[ CAS No. 6326-27-8 ] {[proInfo.proName]}

Name: 6326-27-8|4-Methylbenzimidamide hydrochloride|97%
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SKU: A161764
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Quality Control of [ 6326-27-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 6326-27-8 ]

Product Details of [ 6326-27-8 ]

CAS No. :	6326-27-8	MDL No. :	MFCD00040183
Formula :	C₈H₁₁ClN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MTDUPZAXNYELOU-UHFFFAOYSA-N
M.W :	170.64	Pubchem ID :	122753
Synonyms :

Calculated chemistry of [ 6326-27-8 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	49.64
TPSA :	49.87 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.87 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.07
Log Po/w (WLOGP) :	2.08
Log Po/w (MLOGP) :	2.25
Log Po/w (SILICOS-IT) :	1.57
Consensus Log Po/w :	1.59

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.54
Solubility :	0.492 mg/ml ; 0.00289 mol/l
Class :	Soluble
Log S (Ali) :	-2.75
Solubility :	0.306 mg/ml ; 0.00179 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.48
Solubility :	0.559 mg/ml ; 0.00327 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Safety of [ 6326-27-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 6326-27-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 6326-27-8 ]
Downstream synthetic route of [ 6326-27-8 ]

[ 6326-27-8 ] Synthesis Path-Upstream 1~6

1
[ 104-85-8 ]
[ 6326-27-8 ]

Reference： [1] Australian Journal of Chemistry, 1985, vol. 38, # 5, p. 825 - 833
[2] Journal of the American Chemical Society, 1985, vol. 107, # 9, p. 2743 - 2748
[3] Physical Chemistry Chemical Physics, 2004, vol. 6, # 4, p. 756 - 765
[4] Russian Journal of Organic Chemistry, 2012, vol. 48, # 2, p. 209 - 213
[5] European Journal of Organic Chemistry, 2014, vol. 2014, # 17, p. 3614 - 3621
[6] Tetrahedron Letters, 2018, vol. 59, # 4, p. 361 - 364

2
[ 72525-60-1 ]
[ 104-85-8 ]
[ 6326-27-8 ]

Yield	Reaction Conditions	Operation in experiment
2%	With hydrogenchloride; trimethylsilyl trifluoromethanesulfonate In methanol; dichloromethane; ethyl acetate	Example 7 Synthesis of p-tolylamidine hydrochloride To a solution of hexamethyl disilazane (484 mg) in dichloromethane (1 ml), methanol (96 mg) was added dropwise at room temperature. After cooling on ice, trimethylsilyl trifluoromethanesulfonate (667 mg) was added dropwise to the solution. After the resulting suspension was stirred for 1 hour at room temperature, p-tolunitrile (351 mg) was added dropwise and further stirred for 2 nights at room temperature. The suspension was poured into 2N aqueous sodium hydroxide and extracted with dichloromethane. The extracted solution was dried over anhydrous sodium sulfate and evaporated under reduced pressure to remove the solvent. The resulting residue was purified by column chromatography on silica gel carrying amino groups (liquid phase: dichloromethane/methanol=5/1), followed by addition of 4N solution of hydrogen chloride in ethyl acetate and evaporation under reduced pressure to remove the solvent, thereby giving the titled compound (7 mg, yield 2percent). 1H-NMR (270 MHz, DMSO-d₆) δ: 2.41 (3H, s), 7.43 (2H, d, J=8.0 Hz), 7.74 (2H, d, J=8.0 Hz), 9.06 (2H, s); 9.30 (2H, s).

Reference： [1] Patent: US2003/158442, 2003, A1,

3
[ 19227-13-5 ]
[ 6326-27-8 ]

Reference： [1] Synthetic Communications, 2011, vol. 41, # 15, p. 2195 - 2199

4
[ 43002-64-8 ]
[ 6326-27-8 ]

Reference： [1] Russian Journal of Organic Chemistry, 2012, vol. 48, # 2, p. 209 - 213

5
[ 39739-50-9 ]
[ 6326-27-8 ]

Reference： [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 17, p. 3614 - 3621

6
[ 6326-27-8 ]
[ 77232-38-3 ]

Reference： [1] Helvetica Chimica Acta, 1981, vol. 64, # 1, p. 113 - 152

[ 6326-27-8 ] Synthesis Path-Downstream 1~88

1
[ 6326-27-8 ]
[ 95911-62-9 ]

Yield	Reaction Conditions	Operation in experiment
38%	With sodium hypobromide; lithium bromide In dimethyl sulfoxide for 1h;
34%	With sodium hypobromide; lithium bromide In dimethyl sulfoxide; pentane 1.) below 30 deg C, 5 min, 2.) 0 deg C, 1 h;
	With sodium hypobromide; sodium bromide In hexane; water; dimethyl sulfoxide cooling;

Multi-step reaction with 3 steps 1: 12 percent / NaOCl / H₂O; diethyl ether / 0.08 h / cooling 2: 95 percent / t-BuOCl / CH₂Cl₂ / 24 h / 0 °C 3: LiBr / acetonitrile / 0.17 h / 20 °C

Reference： [1]Moss, Robert A.; Terpinski, Jacek; Cox, D. Phillip; Denneey, Dorothy Z.; Krogh-Jespersen, Karsten [Journal of the American Chemical Society, 1985, vol. 107, # 9, p. 2743 - 2748]
[2]Takeuchi, Ken'ichi; Kitagawa, Toshikazu; Miyabo, Atsushi; Hori, Hideshi; Komatsu, Koichi [Journal of Organic Chemistry, 1993, vol. 58, # 21, p. 5802 - 5810]
[3]Thompson, Robert A.; Francisco, Joseph S.; Grutzner, John B. [Physical Chemistry Chemical Physics, 2004, vol. 6, # 4, p. 756 - 765]
[4]Martinu, Tomas; Dailey, William P. [Journal of Organic Chemistry, 2006, vol. 71, # 13, p. 5012 - 5015]

2
[ 104-85-8 ]
[ 6326-27-8 ]

Yield	Reaction Conditions	Operation in experiment
79%
30%	With sodium methylate; ammonium chloride In methanol at 25℃; 1.) 48 h; 2.) 24 h;
	With ammonium chloride; sodium In methanol at 35℃; for 72h;

	Multi-step reaction with 2 steps 1: hydrogenchloride / benzene / Cooling with ice 2: ammonia / ethanol
	Multi-step reaction with 2 steps 1: hydrogenchloride / diethyl ether / 0 - 5 °C 2: ammonia / methanol / 52 h / 20 °C
	Stage #1: para-methylbenzonitrile With sodium methylate In methanol for 48h; Inert atmosphere; Stage #2: With ammonium chloride In methanol at 20℃; for 24h; Inert atmosphere;	General procedure for synthesis of aryl amidines General procedure: A 100 mL flask was charged with 30 mL of anhydrous MeOH, 10 mmol of the arylnitrile, and 1.0 mmol of sodium methoxide. The complex was protected from moisture and stirred for 48 h. Then, 10 mmol of NH4Cl was added and stirring was continued for 24 h. Unreacted NH4Cl was filtered, and methanol was stripped from the filtrate to afford the product aryl amidine hydrochlorides, which was dissolved in 2.5 mL 8M sodium hydroxide aqueous solution and stirred for 1 h. Then chloroform (20 ml x 3) and H2O (20 ml x 3) were added successively to extract the product, and the combined organic layer was dried with anhydrous MgSO4 and then evaporated under vacuum to remove the organic solvent to give the desired arylamidine.

Reference： [1]Brown; Cronin; Lan; Nardo [Australian Journal of Chemistry, 1985, vol. 38, # 5, p. 825 - 833]
[2]Moss, Robert A.; Terpinski, Jacek; Cox, D. Phillip; Denneey, Dorothy Z.; Krogh-Jespersen, Karsten [Journal of the American Chemical Society, 1985, vol. 107, # 9, p. 2743 - 2748]
[3]Thompson, Robert A.; Francisco, Joseph S.; Grutzner, John B. [Physical Chemistry Chemical Physics, 2004, vol. 6, # 4, p. 756 - 765]
[4]Kuvaeva; Fedorova; Zaitsev; Yakovlev; Zakharov; Semakova [Russian Journal of Organic Chemistry, 2012, vol. 48, # 2, p. 209 - 213]
[5]Golubev, Pavel R.; Pankova, Alena S.; Kuznetsov, Mikhail A. [European Journal of Organic Chemistry, 2014, vol. 2014, # 17, p. 3614 - 3621]
[6]Lu, Xiaodong; Xin, Xiaoyi; Wan, Boshun [Tetrahedron Letters, 2018, vol. 59, # 4, p. 361 - 364]

3
[ 1538-08-5 ]
[ 6326-27-8 ]
3-trifluoromethyl-5-(4-methylphenyl)-1,2,4-triazole [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1999,p. 1301 - 1308

4
[ 82979-45-1 ]
[ 6326-27-8 ]
3-(p-methylphenyl)-2,4-diazabicyclo[4.2.0]octa-1⁽⁶⁾,2-dien-5-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With triethylamine In 1,4-dioxane at 20℃; for 48h;

Reference： [1]Nötzel, Marcus W.; Rauch, Karsten; Labahn, Thomas; De Meijere, Armin [Organic Letters, 2002, vol. 4, # 5, p. 839 - 841]

5
[ 6326-27-8 ]
[ 77232-38-3 ]

Reference： [1]Helvetica Chimica Acta,1981,vol. 64,p. 113 - 152

6
[ 75-70-7 ]
[ 6326-27-8 ]
[ 221038-01-3 ]

Yield	Reaction Conditions	Operation in experiment
44%	With triethylamine In chloroform	8 (Process 8, Scheme 8) To a mixture of p-methylbenzamidine hydrochloride (5.1 g, 30.0 mmol) in CHCl3 (100 ml) is added triethyl amine (15.12 g, 20.9 ml, 150.0 mmol) and cooled to 5° C. in an ice-water bath. To the mixture is slowly added perchloromethyl mercaptan (95%, 6.16 g, 31.5 mmol) in CHCl3 (10 ml) over 1 hour. The yellow solution is allowed to warm up to room temperature. After 2 hours the mixture is washed with water (100 ml*2) and brine (100 ml). The organic layer is dried over MgSO4 and the solvent is removed under reduced pressure to yield a brown oil. The oil is purified on a bed of silica gel, eluding with 1:1 CHCl3:hexanes to yield 3-(p-tolyl)-5-chloro-1,2,4-thiadiazole as a yellow solid (2.78 g, 44%). 1 H NMR (CDCl3): δ2.41 (s, 3H), 7.30(d, 2H), 8.13 (d, 2H).

Reference： [1]Current Patent Assignee: Yu; Dingwei Tim; Macina; Orest Taras; Sircar; Ila; Sircar; Jagadish Chandra; Riviello; Christopher Mark - US6156776, 2000, A

7
[ 88-67-5 ]
[ 6326-27-8 ]
[ 18818-41-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: 2-Iodobenzoic acid; p-methylbenzamidine hydrochloride In N,N-dimethyl-formamide for 0.166667h; Inert atmosphere; Green chemistry; Stage #2: With caesium carbonate In N,N-dimethyl-formamide at 60℃; for 12h; Inert atmosphere; Green chemistry;
88%	With 8-quinolinol; sodium hydroxide; copper dichloride In water at 20℃; for 0.333333h; Sealed tube; Microwave irradiation;	Experimental General procedure: In a 10 mL glass tube 2-iodobenzoic acid (1.0 mmol), acetamidine hydrochloride (1.2 mmol), CuCl2 (0.1 mmol), L2 (0.1 mmol), and NaOH (4.0 equiv.) and 3.0 mL water were placed. The vessel was then sealed with a septum and placed into the microwave cavity. Initial microwave irradiation of 120 W by using a CEM Discover microwave synthesizer was used at the room temperature for 20 min. The reaction mixture was stirred continuously during the reaction. After completion of the reaction, the solvent was removed in vacuo. The residue was purified by silica gel column chromatography to afford the corresponding product. All the products were confirmed by NMR and MS spectroscopic analysis.
82%	Stage #1: 2-Iodobenzoic acid; p-methylbenzamidine hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: With iron(III)-acetylacetonate; caesium carbonate; N,N`-dimethylethylenediamine In N,N-dimethyl-formamide Microwave irradiation; Inert atmosphere;

Reference： [1]He, Wen; Zhao, Hong; Yao, Ruiya; Cai, Mingzhong [RSC Advances, 2014, vol. 4, # 91, p. 50285 - 50294]
[2]Ke, Fang; Liu, Caiqin; Zhang, Peng; Xu, Jianhua; Chen, Xiaole [Synthetic Communications, 2018, vol. 48, # 24, p. 3089 - 3098]
[3]Location in patent: experimental part Zhang, Xiaodong; Ye, Deju; Sun, Haifeng; Guo, Diliang; Wang, Jiang; Huang, He; Zhang, Xu; Jiang, Hualiang; Liu, Hong [Green Chemistry, 2009, vol. 11, # 11, p. 1881 - 1888]

8
[ 6326-27-8 ]
[ 3005-30-9 ]

Yield	Reaction Conditions	Operation in experiment
61%	Stage #1: p-methylbenzamidine hydrochloride With copper; caesium carbonate In dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere; Stage #2: With oxygen In dimethyl sulfoxide at 120℃; for 48h;
58%	With 1,10-Phenanthroline; copper(II) bis(trifluoromethanesulfonate); sodium hydrogencarbonate; potassium hexacyanoferrate(III) In 1,2-dichloro-benzene at 130℃; for 24h; Sealed tube;	4.3 General procedure III for the Cu(OTf)2-catalyzed dimerizationof amidine hydrochlorides General procedure: A dry 10 mL vial was equipped with a magnetic stir bar andcharged with amidine hydrochloride 1 (1.0 mmol), Cu(OTf)2 (18 mg,0.05 mmol), NaHCO3 (252 mg, 3.0 mmol), 1,10-phenanthroline(36 mg, 0.20 mmol), K3[Fe(CN)6] (99 mg, 0.30 mmol) and sealedunder air. Then, freshly distilled o-dichlorobenzene (3 mL) wasadded using a syringe and the reaction mixture was stirred at130 C for 24 h. After cooling to room temperature the reactionmixture was diluted with water (5 mL) and extracted with EtOAc(320 mL). The combined organic layers were dried over anhydrousMgSO4, filtered and evaporated in vacuo. The crude productwas subjected to flash column chromatography over silica gel toyield the product 2. 4.4.3 3,5-Bis(4-methylphenyl)-1H-1,2,4-triazole (2c)23c,31 Compound 1c (171 mg, 1.0 mmol) was reacted under the conditions of general procedure III. Column chromatography over silica gel (petroleum ether/EtOAc=3:1) afforded 3,5-bis(4-methylphenyl)-1H-1,2,4-triazole (2c) as a white solid in 58% yield (72 mg, 0.29 mmol).
50%	With iodine; caesium carbonate In 1,2-dichloro-benzene at 130℃; for 16h; chemoselective reaction;	2. General procedure (A) for the preparation of symmetrical 1,2,4-Triazoles (2a-n): General procedure: To a stirred solution of amidine hydrochloride 1 (1.0 mmol) in o-dichlorobenzene (3.0 mL) was added Cs2CO3 (651 mg, 2.0 mmol) followed by iodine (508 mg, 2.0 mmol) at room temperature. The reaction mixture was stirred at 130 °C for 16 h. After cooling to room temperature the reaction mixture was diluted with 10% aqueous Na2S2O3 (4.0 mL) and the product was extracted with EtOAc (2 × 15 mL). The combined organic layers were dried over anhydrous Na2SO4, filteredand evaporated in vacuum. The crude product was purified by flash column chromatography over silica gel using EtOAc/n-Hexane as the eluent to afford the desired product

Reference： [1]Xu, Hao; Jiang, Yuyang; Fu, Hua [Synlett, 2013, vol. 24, # 1, p. 125 - 129]
[2]Sudheendran, Kavitha; Schmidt, Dietmar; Frey, Wolfgang; Conrad, Jürgen; Beifuss, Uwe [Tetrahedron, 2014, vol. 70, # 8, p. 1635 - 1645]
[3]Inturi, Surendra Babu; Kalita, Biswajit; Ahamed, A. Jafar [Tetrahedron Letters, 2016, vol. 57, # 21, p. 2227 - 2230]

9
[ 3599-89-1 ]
[ 6326-27-8 ]
[ 1216193-88-2 ]

Reference： [1]Synlett,2013,vol. 24,p. 125 - 129

10
[ 57297-29-7 ]
[ 6326-27-8 ]
[ 1251249-97-4 ]

Reference： [1]Synlett,2013,vol. 24,p. 125 - 129

11
[ 615-43-0 ]
[ 6326-27-8 ]
[ 120-03-6 ]

Yield	Reaction Conditions	Operation in experiment
51%	With copper(I) oxide; caesium carbonate; N,N`-dimethylethylenediamine In N,N-dimethyl-formamide at 140℃; for 16h; Inert atmosphere;	General experimental procedure General procedure: A flask was charged with Cu2O (14 mg, 0.1 mmol), Cs2CO3 (977 mg, 3 mmol), o-haloaniline (1 mmol) and amidine hydrochloride (1.5 mmol) in 2 mL DMF under nitrogen atmosphere. The mixture was stirred at room temperature and DMEDA (20 mL, 0.2 mmol) was added via syringe. The reaction mixture was then stirred in a preheated oil bath at 140 C for 16 h, and then cooled to room temperature. The inorganic salt was filtered off and ethyl acetate, water was added. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was dried over Na2SO4, and concentrated in vacuum.The residue was purified by column chromatography on silica gelusing petroleum ether/ethyl acetate as eluent to provide the desired product.

Reference： [1]Qu, Yanyang; Pan, Lei; Wu, Zhiqing; Zhou, Xiangge [Tetrahedron, 2013, vol. 69, # 6, p. 1717 - 1719]

12
[ 6326-27-8 ]
[ 615-36-1 ]
[ 120-03-6 ]

Yield	Reaction Conditions	Operation in experiment
40%	With copper(I) oxide; caesium carbonate; N,N`-dimethylethylenediamine In N,N-dimethyl-formamide at 140℃; for 16h; Inert atmosphere;	General experimental procedure General procedure: A flask was charged with Cu2O (14 mg, 0.1 mmol), Cs2CO3 (977 mg, 3 mmol), o-haloaniline (1 mmol) and amidine hydrochloride (1.5 mmol) in 2 mL DMF under nitrogen atmosphere. The mixture was stirred at room temperature and DMEDA (20 mL, 0.2 mmol) was added via syringe. The reaction mixture was then stirred in a preheated oil bath at 140 C for 16 h, and then cooled to room temperature. The inorganic salt was filtered off and ethyl acetate, water was added. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was dried over Na2SO4, and concentrated in vacuum.The residue was purified by column chromatography on silica gelusing petroleum ether/ethyl acetate as eluent to provide the desired product.

Reference： [1]Qu, Yanyang; Pan, Lei; Wu, Zhiqing; Zhou, Xiangge [Tetrahedron, 2013, vol. 69, # 6, p. 1717 - 1719]

13
[ 6293-83-0 ]
[ 6326-27-8 ]
[ 1571-90-0 ]

Yield	Reaction Conditions	Operation in experiment
68%	With copper(I) oxide; caesium carbonate; N,N`-dimethylethylenediamine In N,N-dimethyl-formamide at 140℃; for 16h; Inert atmosphere;	General experimental procedure General procedure: A flask was charged with Cu2O (14 mg, 0.1 mmol), Cs2CO3 (977 mg, 3 mmol), o-haloaniline (1 mmol) and amidine hydrochloride (1.5 mmol) in 2 mL DMF under nitrogen atmosphere. The mixture was stirred at room temperature and DMEDA (20 mL, 0.2 mmol) was added via syringe. The reaction mixture was then stirred in a preheated oil bath at 140 C for 16 h, and then cooled to room temperature. The inorganic salt was filtered off and ethyl acetate, water was added. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was dried over Na2SO4, and concentrated in vacuum.The residue was purified by column chromatography on silica gelusing petroleum ether/ethyl acetate as eluent to provide the desired product.

Reference： [1]Qu, Yanyang; Pan, Lei; Wu, Zhiqing; Zhou, Xiangge [Tetrahedron, 2013, vol. 69, # 6, p. 1717 - 1719]

14
[ 13296-94-1 ]
[ 6326-27-8 ]
[ 1571-90-0 ]

Yield	Reaction Conditions	Operation in experiment
55%	With copper(I) oxide; caesium carbonate; N,N`-dimethylethylenediamine In N,N-dimethyl-formamide at 140℃; for 16h; Inert atmosphere;	General experimental procedure General procedure: A flask was charged with Cu2O (14 mg, 0.1 mmol), Cs2CO3 (977 mg, 3 mmol), o-haloaniline (1 mmol) and amidine hydrochloride (1.5 mmol) in 2 mL DMF under nitrogen atmosphere. The mixture was stirred at room temperature and DMEDA (20 mL, 0.2 mmol) was added via syringe. The reaction mixture was then stirred in a preheated oil bath at 140 C for 16 h, and then cooled to room temperature. The inorganic salt was filtered off and ethyl acetate, water was added. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was dried over Na2SO4, and concentrated in vacuum.The residue was purified by column chromatography on silica gelusing petroleum ether/ethyl acetate as eluent to provide the desired product.

Reference： [1]Qu, Yanyang; Pan, Lei; Wu, Zhiqing; Zhou, Xiangge [Tetrahedron, 2013, vol. 69, # 6, p. 1717 - 1719]

15
[ 6326-27-8 ]
[ 594-42-3 ]
[ 221038-01-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With triethylamine In dichloromethane at -10 - 20℃; for 3h;	2.a Example 2 l-Benzo[l,3]dioxol-5-ylmethyl-4-(3-p-tolyl-[l,2,4]thiadiazol-5-yl)-piperazine a) 5-Chloro-3-p-tolyl-l,2,4-thiadiazole A mixture of 4-methylbenzimidamide hydrochloride (1.55 g, 9.08 mmol) and Et3N (4.6 g, 6.33 ml, 45.4 mmol) in DCM (30 mL) was cooled with a NaCl/ice-bath to -10°C. Perchloromethyl mercaptan (1.86 g, 1.09 ml, 9.99 mmol) in DCM (10 mL) was added during 40 min. The resulting yellow suspension was stirred for 20 min at 0 °C and 2 h at RT. Water (40 mL) and aq. 2 N NaOH (10 mL) was added. The organic layer was separated and extracted with brine (50 mL). The aqueous layers were extracted with DCM (2 x 40 mL). The combined organic layers were dried over Na2S04, filtered off and concentrated in vacuo. The residue was purified by silica chromatography (Flash 50 g Si- cartridge using AcOEt: Heptane 1 : 19 to 1 :9.) to yield 5-chloro-3-p-tolyl-l,2,4-thiadiazole (1.63 g, 7.74 mmol, 85 % yield) as light yellow solid.

Reference： [1]Current Patent Assignee: REMYND - WO2013/4642, 2013, A1 Location in patent: Page/Page column 51

16
[ 1140899-25-7 ]
[ 6326-27-8 ]
4-amino-6,9-dichloro-2-(p-tolyl)benzo[g]pteridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With triethylamine In tetrahydrofuran Reflux;	5.1. Preparation of 4-amino-2-aryl-6,9-dichlorobenzo[g]pteridines 5 General procedure: A stirred mixture of 5,8-dichloro-2,3-dicyanoquinoxaline 3(2 mmol), the corresponding benzamidine hydrochloride (2.1 mmol), and triethylamine (4.4 mmol), in THF (15 mL), was refluxed until complete consumption of 3 (clearly detectable by silica gel TLC, ethyl acetate/hexane 1:2). The reaction time varied from 2 to 6 h depending on the benzamidine hydrochloride used.The solvent was then removed under reduced pressure. The residue was vigorously stirred in water (20 mL) for 30 min, leaving a solid that was collected by vacuum filtration and crystallized in the appropriate solvent. Preparation of product 5g was carried out in DMF instead of THF, in the presence of 7 mmol of triethylamine (benzamidine 4g was available as dihydrochloride) at 80 °Cfor 12 h.

Reference： [1]Guirado, Antonio; López Sánchez, José I.; Ruiz-Alcaraz, Antonio J.; García-Peñarrubia, Pilar; Bautista, Delia; Gálvez, Jesús [European Journal of Medicinal Chemistry, 2013, vol. 66, p. 269 - 275]

17
[ 3959-05-5 ]
[ 6326-27-8 ]
2-p-tolyl-quinazoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	Stage #1: 2-bromobenzylamine; p-methylbenzamidine hydrochloride With potassium carbonate; copper(I) bromide In dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere; Schlenk technique; Stage #2: In dimethyl sulfoxide at 100℃; for 0.5h; Schlenk technique;	General procedure for synthesis of compounds 3a-v General procedure: A 25 mL Schlenk tube wascharged with a magnetic stirrer and DMSO (2.0 mL). Substituted(2-bromophenyl)methylamine (1) (0.5 mmol), amidine hydrochloride (2) (1.0 mmol),CuBr (0.1 mmol, 14.2 mg), and K2CO3 (1.5 mmol, 207 mg) were added to the tube.The mixture was stirred at 80-120 oC under nitrogen atmosphere for 24 h, and thenunder air for 0.5 h. The resulting mixture was cooled to room temperature and filtered,and the solid was washed with ethyl acetate for two times (3 × 3 mL). The combinedfiltrate was concentrated by the rotary evaporator, and the residue was purified bycolumn chromatography on silica gel using petroleum ether/ ethyl acetate as eluent togive the desired target product.
65%	With potassium phosphate; copper(l) iodide; Trimethylacetic acid In 1,2-dichloro-benzene at 110℃; for 18h; Sealed tube;	4.2. General procedure for the CuI-catalyzed synthesis ofcompounds 3a-t General procedure: Anoven-dried 10mLvialwas charged with CuI (9mg, 0.05mmol),K3PO4 (318 mg, 1.5 mmol), pivalic acid (20 mg, 0.2 mmol), a 1-(2-bromophenyl)methanamine 1 (0.5 mmol), and an amidinium salt 2or an imidate salt 4 (0.5 mmol) under air. After sealing the vial, dry1,2-dichlorobenzene (3 mL) was added by syringe and the reactionmixture was stirred at 110 C (oil bath temperature) for 18 h. Aftercooling to room temperature, the vial was opened and the reactionmixturewas partitioned between CH2Cl2 (30 mL) and brine (20 mL).The aqueous phase was extracted with CH2Cl2 (220 mL). Thecombined organic layers were dried over anhydrous MgSO4 andconcentrated in vacuum. The residue was purified by flash chromatographyon silica gel to afford the desired product.

Reference： [1]Liu, Qing; Zhao, Yufen; Fu, Hua; Cheng, Changmei [Synlett, 2013, vol. 24, # 16, p. 2089 - 2094]
[2]Omar, Mohamed A.; Conrad, Jürgen; Beifuss, Uwe [Tetrahedron, 2014, vol. 70, # 18, p. 3061 - 3072]

18
[ 887581-09-1 ]
[ 6326-27-8 ]
[ 1255516-30-3 ]

Yield	Reaction Conditions	Operation in experiment
71%		General procedure: A 25 mL Schlenk tube wascharged with a magnetic stirrer and DMSO (2.0 mL). Substituted(2-bromophenyl)methylamine (1) (0.5 mmol), amidine hydrochloride (2) (1.0 mmol),CuBr (0.1 mmol, 14.2 mg), and K2CO3 (1.5 mmol, 207 mg) were added to the tube.The mixture was stirred at 80-120 oC under nitrogen atmosphere for 24 h, and thenunder air for 0.5 h. The resulting mixture was cooled to room temperature and filtered,and the solid was washed with ethyl acetate for two times (3 × 3 mL). The combinedfiltrate was concentrated by the rotary evaporator, and the residue was purified bycolumn chromatography on silica gel using petroleum ether/ ethyl acetate as eluent togive the desired target product.

Reference： [1]Synlett,2013,vol. 24,p. 2089 - 2094

19
1-(2-bromo-4-fluorophenyl)methan-1-amine [ No CAS ]
[ 6326-27-8 ]
7-fluoro-2-(p-tolyl)quinazoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	Stage #1: 1-(2-bromo-4-fluorophenyl)methan-1-amine; p-methylbenzamidine hydrochloride With potassium carbonate; copper(I) bromide In dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere; Schlenk technique; Stage #2: In dimethyl sulfoxide at 100℃; for 0.5h; Schlenk technique;	General procedure for synthesis of compounds 3a-v General procedure: A 25 mL Schlenk tube wascharged with a magnetic stirrer and DMSO (2.0 mL). Substituted(2-bromophenyl)methylamine (1) (0.5 mmol), amidine hydrochloride (2) (1.0 mmol),CuBr (0.1 mmol, 14.2 mg), and K2CO3 (1.5 mmol, 207 mg) were added to the tube.The mixture was stirred at 80-120 oC under nitrogen atmosphere for 24 h, and thenunder air for 0.5 h. The resulting mixture was cooled to room temperature and filtered,and the solid was washed with ethyl acetate for two times (3 × 3 mL). The combinedfiltrate was concentrated by the rotary evaporator, and the residue was purified bycolumn chromatography on silica gel using petroleum ether/ ethyl acetate as eluent togive the desired target product.

Reference： [1]Liu, Qing; Zhao, Yufen; Fu, Hua; Cheng, Changmei [Synlett, 2013, vol. 24, # 16, p. 2089 - 2094]

20
[ 6326-27-8 ]
[ 100-51-6 ]
[ 7753-06-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	With oxygen; copper(II) acetate monohydrate; sodium carbonate In toluene at 110℃; for 24h;
87%	With copper(II) acetate monohydrate; sodium carbonate In toluene at 110℃; for 24h;	7 Synthesis of 2-phenyl-4,6-di-p-tolyl-1,3,5-triazine, including the following steps: 20 mmol of 4-methylbenzamidine hydrochloride and 13 mmol of benzyl alcohol were taken in a 100 mL round bottom flask. 2 mmol Cu(OAc)2·H2O was added to it, 20 mmol Na2CO3 and 30mL toluene were added and stirred at 110 ° C for 24 hours. The product was extracted with ethyl acetate and dried to obtain a crude product. The crude product was purified by silica gel column chromatography (solvent volume ratio petroleum ether: ethyl acetate = 100:1) to give a white solid, 2-phenyl-4,6-di-p-tolyl-1,3,5-triazine, yield 87%. The melting point is 233 ° C.
78%	With bis(3,5-di-(tert-butyl)-2-hydroxyazobenzolato)nickel(II); potassium <i>tert</i>-butylate; oxygen In toluene at 80℃; for 8h;

71%	Stage #1: p-methylbenzamidine hydrochloride; benzyl alcohol With caesium carbonate In dimethyl sulfoxide at 20℃; for 0.0833333h; Schlenk technique; Green chemistry; Stage #2: With N-iodo-succinimide In dimethyl sulfoxide at 100℃; for 16h; Schlenk technique; Green chemistry;
66%	With μ-diiodo-di((η5-pentamethylcyclopentadienyl)(iodo)iridium); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 20 - 110℃; for 20h;	Typical procedure for the synthesis of 3a. General procedure: [Cp*IrI2]2 (1 mol %, 0.01 mmol), xantphos (2 mol %,0.02 mmol) and dioxane (2 mL) were stirred shortly in a Schlenk tube at room temperature. Subsequently, 3-pyridinemethanol (2.0 mmol), benzamidine hydrochloride(1.0 mmol), and cesium carbonate (1.0 mmol)were added. The mixture was heated under 110°C for 20 h and then cooled down to room temperature. The resulting solution was purified by column chromatography with petroleum ether-ethyl acetate(10 : 1) as an eluent to give 2,4-diphenyl-6-(pyridin-3-yl)-1,3,5-triazine (3a) as a white solid.
64%	With [RhCl₂(p-cymene)]2; caesium carbonate In dimethyl sulfoxide at 110℃; for 16h; Sealed tube;

Reference： [1]You, Qing; Wang, Fei; Wu, Chaoting; Shi, Tianchao; Min, Dewen; Chen, Huajun; Zhang, Wu [Organic and Biomolecular Chemistry, 2015, vol. 13, # 24, p. 6723 - 6727]
[2]Current Patent Assignee: ANHUI NORMAL UNIVERSITY - CN104262273, 2017, B Location in patent: Paragraph 0070-0072
[3]Bains, Amreen K.; Adhikari, Debashis [Catalysis science and technology, 2020, vol. 10, # 18, p. 6309 - 6318]
[4]Tiwari, Abhishek R.; Akash; Bhanage, Bhalchandra M. [Organic and Biomolecular Chemistry, 2015, vol. 13, # 45, p. 10973 - 10976]
[5]Shi, Gang; He, Fei; Che, Youxin; Ni, Caihua; Li, Ying [Russian Journal of General Chemistry, 2016, vol. 86, # 2, p. 380 - 386][Zh. Obshch. Khim., 2016, vol. 86, # 2, p. 380 - 386,7]
[6]Xie, Feng; Chen, Mengmeng; Wang, Xiaoting; Jiang, Huanfeng; Zhang, Min [Organic and Biomolecular Chemistry, 2014, vol. 12, # 17, p. 2761 - 2768]

21
[ 6326-27-8 ]
[ 105-13-5 ]
[ 1596320-76-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With bis(3,5-di-(tert-butyl)-2-hydroxyazobenzolato)nickel(II); potassium <i>tert</i>-butylate; oxygen In toluene at 80℃; for 8h;
76%	Stage #1: p-methylbenzamidine hydrochloride; 4-Methoxybenzyl alcohol With caesium carbonate In dimethyl sulfoxide at 20℃; for 0.0833333h; Schlenk technique; Green chemistry; Stage #2: With N-iodo-succinimide In dimethyl sulfoxide at 100℃; for 16h; Schlenk technique; Green chemistry;
71%	With μ-diiodo-di((η5-pentamethylcyclopentadienyl)(iodo)iridium); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 20 - 110℃; for 20h;	Typical procedure for the synthesis of 3a. General procedure: [Cp*IrI2]2 (1 mol %, 0.01 mmol), xantphos (2 mol %,0.02 mmol) and dioxane (2 mL) were stirred shortly in a Schlenk tube at room temperature. Subsequently, 3-pyridinemethanol (2.0 mmol), benzamidine hydrochloride(1.0 mmol), and cesium carbonate (1.0 mmol)were added. The mixture was heated under 110°C for 20 h and then cooled down to room temperature. The resulting solution was purified by column chromatography with petroleum ether-ethyl acetate(10 : 1) as an eluent to give 2,4-diphenyl-6-(pyridin-3-yl)-1,3,5-triazine (3a) as a white solid.

68%

With [RhCl₂(p-cymene)]2; caesium carbonate In dimethyl sulfoxide at 110℃; for 16h; Sealed tube;

Reference： [1]Bains, Amreen K.; Adhikari, Debashis [Catalysis science and technology, 2020, vol. 10, # 18, p. 6309 - 6318]
[2]Tiwari, Abhishek R.; Akash; Bhanage, Bhalchandra M. [Organic and Biomolecular Chemistry, 2015, vol. 13, # 45, p. 10973 - 10976]
[3]Shi, Gang; He, Fei; Che, Youxin; Ni, Caihua; Li, Ying [Russian Journal of General Chemistry, 2016, vol. 86, # 2, p. 380 - 386][Zh. Obshch. Khim., 2016, vol. 86, # 2, p. 380 - 386,7]
[4]Xie, Feng; Chen, Mengmeng; Wang, Xiaoting; Jiang, Huanfeng; Zhang, Min [Organic and Biomolecular Chemistry, 2014, vol. 12, # 17, p. 2761 - 2768]

22
[ 6326-27-8 ]
[ 873-76-7 ]
[ 7752-00-3 ]

Yield	Reaction Conditions	Operation in experiment
96%	With oxygen; copper(II) acetate monohydrate; sodium carbonate In toluene at 110℃; for 24h;
71%	With bis(3,5-di-(tert-butyl)-2-hydroxyazobenzolato)nickel(II); potassium <i>tert</i>-butylate; oxygen In toluene at 80℃; for 8h;
70%	Stage #1: p-methylbenzamidine hydrochloride; para-Chlorobenzyl alcohol With caesium carbonate In dimethyl sulfoxide at 20℃; for 0.0833333h; Schlenk technique; Green chemistry; Stage #2: With N-iodo-succinimide In dimethyl sulfoxide at 100℃; for 16h; Schlenk technique; Green chemistry;

61%	With [RhCl₂(p-cymene)]2; caesium carbonate In dimethyl sulfoxide at 110℃; for 16h; Sealed tube;
61%	With μ-diiodo-di((η5-pentamethylcyclopentadienyl)(iodo)iridium); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 20 - 110℃; for 20h;	Typical procedure for the synthesis of 3a. General procedure: [Cp*IrI2]2 (1 mol %, 0.01 mmol), xantphos (2 mol %,0.02 mmol) and dioxane (2 mL) were stirred shortly in a Schlenk tube at room temperature. Subsequently, 3-pyridinemethanol (2.0 mmol), benzamidine hydrochloride(1.0 mmol), and cesium carbonate (1.0 mmol)were added. The mixture was heated under 110°C for 20 h and then cooled down to room temperature. The resulting solution was purified by column chromatography with petroleum ether-ethyl acetate(10 : 1) as an eluent to give 2,4-diphenyl-6-(pyridin-3-yl)-1,3,5-triazine (3a) as a white solid.

Reference： [1]You, Qing; Wang, Fei; Wu, Chaoting; Shi, Tianchao; Min, Dewen; Chen, Huajun; Zhang, Wu [Organic and Biomolecular Chemistry, 2015, vol. 13, # 24, p. 6723 - 6727]
[2]Bains, Amreen K.; Adhikari, Debashis [Catalysis science and technology, 2020, vol. 10, # 18, p. 6309 - 6318]
[3]Tiwari, Abhishek R.; Akash; Bhanage, Bhalchandra M. [Organic and Biomolecular Chemistry, 2015, vol. 13, # 45, p. 10973 - 10976]
[4]Xie, Feng; Chen, Mengmeng; Wang, Xiaoting; Jiang, Huanfeng; Zhang, Min [Organic and Biomolecular Chemistry, 2014, vol. 12, # 17, p. 2761 - 2768]
[5]Shi, Gang; He, Fei; Che, Youxin; Ni, Caihua; Li, Ying [Russian Journal of General Chemistry, 2016, vol. 86, # 2, p. 380 - 386][Zh. Obshch. Khim., 2016, vol. 86, # 2, p. 380 - 386,7]

23
[ 100-55-0 ]
[ 6326-27-8 ]
[ 1596320-84-1 ]

Yield	Reaction Conditions	Operation in experiment
56%	With μ-diiodo-di((η5-pentamethylcyclopentadienyl)(iodo)iridium); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 20 - 110℃; for 20h;	Typical procedure for the synthesis of 3a. General procedure: [Cp*IrI2]2 (1 mol %, 0.01 mmol), xantphos (2 mol %,0.02 mmol) and dioxane (2 mL) were stirred shortly in a Schlenk tube at room temperature. Subsequently, 3-pyridinemethanol (2.0 mmol), benzamidine hydrochloride(1.0 mmol), and cesium carbonate (1.0 mmol)were added. The mixture was heated under 110°C for 20 h and then cooled down to room temperature. The resulting solution was purified by column chromatography with petroleum ether-ethyl acetate(10 : 1) as an eluent to give 2,4-diphenyl-6-(pyridin-3-yl)-1,3,5-triazine (3a) as a white solid.
54%	With [RhCl₂(p-cymene)]2; caesium carbonate In dimethyl sulfoxide at 110℃; for 16h; Sealed tube;

Reference： [1]Shi, Gang; He, Fei; Che, Youxin; Ni, Caihua; Li, Ying [Russian Journal of General Chemistry, 2016, vol. 86, # 2, p. 380 - 386][Zh. Obshch. Khim., 2016, vol. 86, # 2, p. 380 - 386,7]
[2]Xie, Feng; Chen, Mengmeng; Wang, Xiaoting; Jiang, Huanfeng; Zhang, Min [Organic and Biomolecular Chemistry, 2014, vol. 12, # 17, p. 2761 - 2768]

24
[ 63071-10-3 ]
[ 6326-27-8 ]
[ 1596320-89-6 ]

Yield	Reaction Conditions	Operation in experiment
58%	With mu-diiodo-di((eta5-pentamethylcyclopentadienyl)(iodo)iridium); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 20 - 110℃; for 20h;	General procedure: [Cp*IrI2]2 (1 mol %, 0.01 mmol), xantphos (2 mol %,0.02 mmol) and dioxane (2 mL) were stirred shortly in a Schlenk tube at room temperature. Subsequently, 3-pyridinemethanol (2.0 mmol), benzamidine hydrochloride(1.0 mmol), and cesium carbonate (1.0 mmol)were added. The mixture was heated under 110C for 20 h and then cooled down to room temperature. The resulting solution was purified by column chromatography with petroleum ether-ethyl acetate(10 : 1) as an eluent to give 2,4-diphenyl-6-(pyridin-3-yl)-1,3,5-triazine (3a) as a white solid.

Reference： [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 2761 - 2768
[2]Russian Journal of General Chemistry,2016,vol. 86,p. 380 - 386
Zh. Obshch. Khim.,2016,vol. 86,p. 380 - 386,7

25
[ 6326-27-8 ]
[ 3005-30-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With 1,10-Phenanthroline; copper diacetate; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 24h; Inert atmosphere; Schlenk technique;	General Procedure for the Synthesis of Compounds 2a-o General procedure: To a round-bottom flask (25 mL) equipped with a spherical condenser (40 cm length) were added amidine hydrochloride 1 (1.0 mmol), Cu(OAc)2 (0.2 equiv), K2CO3 (2.0 equiv), 1,10-phenanthroline (0.1 equiv) and anhyd DMF (2.0 mL). Then the mixture was well stirred at 130°C under an inert atmosphere. After cooling off, the mixture was filtered through a pad of celite eluting with CH2Cl2 (3×6 mL). The volatiles were removed under reduced pressure and the residue was purified by a short flash silica gel column chromatography to give compound 2.

Reference： [1]Li, Zhonglian; Zhang, Zhiguo; Zhang, Wei; Liu, Qingfeng; Liu, Tongxin; Zhang, Guisheng [Synlett, 2013, vol. 24, # 20, p. 2735 - 2739]

26
[ 6326-27-8 ]
[ 67496-29-1 ]
[ 1255516-36-9 ]

Yield	Reaction Conditions	Operation in experiment
61%	With potassium phosphate; copper(l) iodide; Trimethylacetic acid; In 1,2-dichloro-benzene; at 110℃; for 18h;Sealed tube;	General procedure: Anoven-dried 10mLvialwas charged with CuI (9mg, 0.05mmol),K3PO4 (318 mg, 1.5 mmol), pivalic acid (20 mg, 0.2 mmol), a 1-(2-bromophenyl)methanamine 1 (0.5 mmol), and an amidinium salt 2or an imidate salt 4 (0.5 mmol) under air. After sealing the vial, dry1,2-dichlorobenzene (3 mL) was added by syringe and the reactionmixture was stirred at 110 C (oil bath temperature) for 18 h. Aftercooling to room temperature, the vial was opened and the reactionmixturewas partitioned between CH2Cl2 (30 mL) and brine (20 mL).The aqueous phase was extracted with CH2Cl2 (220 mL). Thecombined organic layers were dried over anhydrous MgSO4 andconcentrated in vacuum. The residue was purified by flash chromatographyon silica gel to afford the desired product.

Reference： [1]Tetrahedron,2014,vol. 70,p. 3061 - 3072

27
1-(2-bromo-4-methylphenyl)methanamine [ No CAS ]
[ 6326-27-8 ]
[ 1600535-90-7 ]

Yield	Reaction Conditions	Operation in experiment
57%	With potassium phosphate; copper(l) iodide; Trimethylacetic acid In 1,2-dichloro-benzene at 110℃; for 18h; Sealed tube;	4.2. General procedure for the CuI-catalyzed synthesis ofcompounds 3a-t General procedure: Anoven-dried 10mLvialwas charged with CuI (9mg, 0.05mmol),K3PO4 (318 mg, 1.5 mmol), pivalic acid (20 mg, 0.2 mmol), a 1-(2-bromophenyl)methanamine 1 (0.5 mmol), and an amidinium salt 2or an imidate salt 4 (0.5 mmol) under air. After sealing the vial, dry1,2-dichlorobenzene (3 mL) was added by syringe and the reactionmixture was stirred at 110 C (oil bath temperature) for 18 h. Aftercooling to room temperature, the vial was opened and the reactionmixturewas partitioned between CH2Cl2 (30 mL) and brine (20 mL).The aqueous phase was extracted with CH2Cl2 (220 mL). Thecombined organic layers were dried over anhydrous MgSO4 andconcentrated in vacuum. The residue was purified by flash chromatographyon silica gel to afford the desired product.

Reference： [1]Omar, Mohamed A.; Conrad, Jürgen; Beifuss, Uwe [Tetrahedron, 2014, vol. 70, # 18, p. 3061 - 3072]

28
[ 747392-34-3 ]
[ 6326-27-8 ]
[ 1600535-93-0 ]

Yield	Reaction Conditions	Operation in experiment
62%	With potassium phosphate; copper(l) iodide; Trimethylacetic acid; In 1,2-dichloro-benzene; at 110℃; for 18h;Sealed tube;	General procedure: Anoven-dried 10mLvialwas charged with CuI (9mg, 0.05mmol),K3PO4 (318 mg, 1.5 mmol), pivalic acid (20 mg, 0.2 mmol), a 1-(2-bromophenyl)methanamine 1 (0.5 mmol), and an amidinium salt 2or an imidate salt 4 (0.5 mmol) under air. After sealing the vial, dry1,2-dichlorobenzene (3 mL) was added by syringe and the reactionmixture was stirred at 110 C (oil bath temperature) for 18 h. Aftercooling to room temperature, the vial was opened and the reactionmixturewas partitioned between CH2Cl2 (30 mL) and brine (20 mL).The aqueous phase was extracted with CH2Cl2 (220 mL). Thecombined organic layers were dried over anhydrous MgSO4 andconcentrated in vacuum. The residue was purified by flash chromatographyon silica gel to afford the desired product.

Reference： [1]Tetrahedron,2014,vol. 70,p. 3061 - 3072

29
[ 6326-27-8 ]
[ 33513-42-7 ]
[ 39238-44-3 ]

Yield	Reaction Conditions	Operation in experiment
72%	With pyridine; copper(l) iodide; oxygen; triethylamine at 90℃; for 14h;
63%	With oxygen; copper(II) acetate monohydrate; sodium carbonate In toluene at 110℃; for 24h;

Reference： [1]Xu, Xiaowen; Zhang, Min; Jiang, Huanfeng; Zheng, Jia; Li, Yiqun [Organic Letters, 2014, vol. 16, # 13, p. 3540 - 3543]
[2]You, Qing; Wang, Fei; Wu, Chaoting; Shi, Tianchao; Min, Dewen; Chen, Huajun; Zhang, Wu [Organic and Biomolecular Chemistry, 2015, vol. 13, # 24, p. 6723 - 6727]

30
[ 26113-44-0 ]
[ 6326-27-8 ]
[ 68-12-2 ]
[ 1613637-86-7 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 3540 - 3543

31
[ 21739-93-5 ]
[ 6326-27-8 ]
[ 82256-09-5 ]

Reference： [1]RSC Advances,2014,vol. 4,p. 50285 - 50294

32
[ 394-28-5 ]
[ 6326-27-8 ]
C₁₅H₁₁FN₂O [ No CAS ]

Reference： [1]RSC Advances,2014,vol. 4,p. 50285 - 50294

33
[ 6967-82-4 ]
[ 6326-27-8 ]
[ 82256-07-3 ]

Reference： [1]RSC Advances,2014,vol. 4,p. 50285 - 50294

34
[ 6326-27-8 ]
[ 67-68-5 ]
[ 39238-44-3 ]

Yield	Reaction Conditions	Operation in experiment
79%	With potassium phosphate; oxygen; copper diacetate at 100℃; for 8h;
46%	With oxygen; copper(II) acetate monohydrate; sodium carbonate In toluene at 110℃; for 24h;

Reference： [1]Huang, Huawen; Guo, Wei; Wu, Wanqing; Li, Chao-Junx; Jiang, Huanfeng [Organic Letters, 2015, vol. 17, # 12, p. 2894 - 2897]
[2]You, Qing; Wang, Fei; Wu, Chaoting; Shi, Tianchao; Min, Dewen; Chen, Huajun; Zhang, Wu [Organic and Biomolecular Chemistry, 2015, vol. 13, # 24, p. 6723 - 6727]

35
[ 6326-27-8 ]
[ 121-44-8 ]
[ 3599-62-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium phosphate; oxygen; copper diacetate In toluene at 100℃; for 10h;

Reference： [1]Huang, Huawen; Guo, Wei; Wu, Wanqing; Li, Chao-Junx; Jiang, Huanfeng [Organic Letters, 2015, vol. 17, # 12, p. 2894 - 2897]

36
[ 589-18-4 ]
[ 6326-27-8 ]
[ 6726-45-0 ]

Yield	Reaction Conditions	Operation in experiment
86%	With oxygen; copper(II) acetate monohydrate; sodium carbonate In toluene at 110℃; for 24h;
86%	With copper(II) acetate monohydrate; sodium carbonate In toluene at 110℃; for 24h;	8 Synthesis of 2,4,6-tri-p-tolyl-1,3,5-triazine, including the following steps: 20 mmol of 4-methylbenzamidine hydrochloride and 12 mmol of 4-methylbenzyl alcohol were taken in a 100 mL round bottom flask, 2 mmol Cu(OAc)2·H2O was added to it, 20mmol Na2CO3 and 30mL toluene were added and stirred at 110 ° C for 24 hours. The product was extracted with ethyl acetate and dried to obtain a crude product. The crude product was purified by silica gel column chromatography (solvent volume ratio petroleum ether: Ethyl acetate = 100:1) to give a white solid, ie, 2,4,6-tri-p-tolyl-1,3,5-triazine, yield 86%. The melting point is 321 ° C.
66%	With bis(3,5-di-(tert-butyl)-2-hydroxyazobenzolato)nickel(II); potassium <i>tert</i>-butylate; oxygen In toluene at 80℃; for 8h;

37
[ 459-56-3 ]
[ 6326-27-8 ]
2-(4-fluorophenyl)-4,6-di-p-tolyl-1,3,5-triazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With oxygen; copper(II) acetate monohydrate; sodium carbonate In toluene at 110℃; for 24h;
75%	With bis(3,5-di-(tert-butyl)-2-hydroxyazobenzolato)nickel(II); potassium <i>tert</i>-butylate; oxygen In toluene at 80℃; for 8h;

38
[ 2579-22-8 ]
[ 6326-27-8 ]
[ 77232-22-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	With (triphenylphosphine)gold(I) chloride; potassium carbonate In dichloromethane at 20℃; for 3h;
87%	With potassium carbonate In dichloromethane at 20℃; for 3h;	General procedure for heterogeneous Au(I)-catalyzed synthesis of pyrimidines General procedure: A mixture of ynal 1 (0.5 mmol), amidine hydrochloride 2 (0.6 mmol), K2CO3(1.0 mmol), and MCM-41-PPh3-AuCl (41 mg, 0.015 mmol) in DCM (3mL) was stirred at room temperature for 3 h (TLC monitored). The resulting mixture was then diluted with ethyl acetate (15 mL) and filtered. The gold catalyst was washed with distilled water(5 mL), and dry ethanol (25mL) and reused in the next run. The filtrate was concentrated under reduced pressure and the residue was purified by chromatography on silicagel (eluent: petroleum ether/ethyl acetate) to afford the desired product 3.

Reference： [1]Zhan, Haiying; Chen, Longbin; Tan, Jingwen; Cao, Hua [Catalysis Communications, 2016, vol. 73, p. 109 - 112]
[2]Jiang, Minhua; Nie, Quan; Cai, Mingzhong [Synthetic Communications, 2019, vol. 49, # 19, p. 2488 - 2500]

39
[ 6326-27-8 ]
[ 104-55-2 ]
[ 77232-22-5 ]

Yield	Reaction Conditions	Operation in experiment
74%	With oxygen; potassium hydroxide In dimethyl sulfoxide at 120℃; for 12h; Green chemistry;	2.1 General procedure for 3aa General procedure: A mixture of benzamidine hydrochloride 1a (0.25mmol), cinnamaldehyde 2a (0.30mol) and KOH (0.50mmol, 2equiv.) was stirred in DMSO (1.0mL) under 1atm O2 atmosphere at 120°C for 12h. After completion of the reaction (monitored by TLC), water (10mL) was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The combined organic layers were then dried over MgSO4, filtered, and then concentrated in vacuo. The residue was purified by flash chromatography on silica gel to give the desired product 3aa as a white solid (using the mixture of petroleum ether and ethyl acetate as eluents).

Reference： [1]Guo, Wei [Chinese Chemical Letters, 2016, vol. 27, # 1, p. 47 - 50]

40
[ 1501-06-0 ]
[ 6326-27-8 ]
3-[4-methyl-2-(4-methylphenyl)-6-oxo-1,6-dihydropyrimidine-5-yl]propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: p-methylbenzamidine hydrochloride With sodium In ethanol for 0.166667h; Stage #2: diethyl 2-acetylglutarate In ethanol for 6h; Reflux; Stage #3: With sodium hydroxide In ethanol; water for 4h; Reflux;	3-[4-Methyl-2-(4-methylphenyl)-6-oxo-1,6-dihydropyrimidine-5-yl]propanoic acid (1a). To a solution of 4.6 g (0.2 mol) of sodium in 150 mL of anhydrous EtOH was added 17.01 g (0.1 mol) of 4-methylbenzamidine hydrochloride, the mixture was stirred for 10 min, to the suspension 23.0 g (0.1 mol) of diethyl ether 2-acetylpentanedioate was added, the reaction mixture was boiled for 6 h and then 2/3 of ethanol was distilled off. To the residue 5.0 g (0.125 mol) of NaOH was added, the mixture was boiled for 4 h, acidified with HCl to pH 6 and left overnight in the cold. The precipitate was filtered off and dried. Yield 19.6 g (72%), mp 239-241°C, Rf 0.46. IR spectrum, ν, cm-1: 1698 (CO), 1627 (C=C-C=N). 1H NMR spectrum (DMSO-d6), δ, ppm: 2.32 s (3H, CH3), 2.33 s (3H, CH3), 2.38-2.44 m (2H, CH2), 2.64-2.71 m (2H, CH2), 7.27-7.33 m (2H) and 7.95-8.01 m (2H, C6H4), 12.31 br.s (2H, COOH, NH). Found, %: N 9.98. C15H16N2O3. Calculated, %: N 10.29.

Reference： [1]Harutyunyan [Russian Journal of Organic Chemistry, 2016, vol. 52, # 2, p. 235 - 239][Zh. Org. Khim., 2016, vol. 52, # 2, p. 252 - 256,5]

41
[ 63190-44-3 ]
[ 6326-27-8 ]
[ 3005-30-9 ]
5-cyclopropyl-3-(p-tolyl)-1H-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 38% 2: 10%	With iodine; caesium carbonate In 1,2-dichloro-benzene at 130℃; for 16h; chemoselective reaction;	3. General procedure (B) for the preparation of unsymmetrical 1,2,4-Triazoles (4a-g): General procedure: To a stirred solution of amidine hydrochloride 1 (1.0 mmol) and imidate hydrochloride 3 (2.0 mmol) in o-dichlorobenzene (4.0 mL) was added Cs2CO3 (1.3g, 4.0 mmol) followed by iodine (254 mg, 1.0 mmol) at room temperature. The reaction mixture was stirred at 130 °C for 16 h. After cooling to room temperature the reaction mixture was diluted with 10% aqueous Na2S2O3 (4.0 mL) and the product was extracted with EtOAc (2 × 15 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated in vacuum. The crude product was purified by flash column chromatography over silica gel using EtOAc/n-Hexane as the eluent to afford the desired product 4.

Reference： [1]Inturi, Surendra Babu; Kalita, Biswajit; Ahamed, A. Jafar [Tetrahedron Letters, 2016, vol. 57, # 21, p. 2227 - 2230]

42
[ 91-56-5 ]
[ 6326-27-8 ]
[ 18818-41-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With tert.-butylhydroperoxide; potassium phosphate In water; dimethyl sulfoxide at 25 - 30℃; for 6h; Sealed tube;

Reference： [1]Jia, Feng-Cheng; Zhou, Zhi-Wen; Xu, Cheng; Wu, Yan-Dong; Wu, An-Xin [Organic Letters, 2016, vol. 18, # 12, p. 2942 - 2945]

43
[ 21100-66-3 ]
[ 6326-27-8 ]
[ 77232-22-5 ]

Yield	Reaction Conditions	Operation in experiment
67%	With potassium carbonate In acetonitrile for 12h; Reflux; Inert atmosphere;	1 One-pot general procedure for the synthesis of 2,4-diarylpyrimidines 7e-p General procedure: To a solution of 6 (1.0 mmol) in dry THF (25 mL) a 1.0 M solution of potassium tert-butoxide (1.0 mmol) in dry THF was added dropwise and the mixture was stirred for 4 h. After filtration the solvent was removed in vacuo, the solid residue was washed with a cool ethanol (3 mL) and crystallised from ethanol. 4.7.1 2-(4-Methylphenyl)-4-phenylpyrimidine (7e) Yellow needles (hexane). Mp: 91-92 °C (Lit, 59 mp 91-94 °C). (Found C 82.55; H 5.98; N 11.42; C17H14N2 requires C 82.90; H 5.73; N 11.37); 1H NMR δ (CDCl3, 300 MHz): 2.45 (s, 3H), 7.32-7.36 (m, 2H), 7.53-7.56 (m, 4H), 8.21-8.25 (m, 2H), 8.48-8.53 (m, 2H), 8.81 (d, 1H, J=5.4 Hz); 13C NMR δ (CDCl3, 75.4 MHz): 21.47, 114.17, 127.13, 128.19, 128.85, 129.25, 130.83, 135.11, 136.98, 140.89, 157.71, 163.70, 164.56; MS (EI) m/z (%): 246 (M+, 100), 247 (38), 231 (4), 169 (6), 129 (30), 117 (32), 102 (59); IR (KBr): 1583, 1547, 1492, 1452, 1426, 1406, 1382, 1277, 1175, 830, 765, 688 cm-1.

Reference： [1]Guirado, Antonio; Alarcón, Enrique; Vicente, Yesica; Andreu, Raquel; Bautista, Delia; Gálvez, Jesús [Tetrahedron, 2016, vol. 72, # 27-28, p. 3922 - 3929]

44
[ 69808-96-4 ]
[ 6326-27-8 ]
4-(4-methoxyphenyl)-2-(4-methylphenyl)pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With potassium carbonate In acetonitrile for 12h; Reflux; Inert atmosphere;	4 One-pot general procedure for the synthesis of 2,4-diarylpyrimidines 7e-p General procedure: To a solution of 6 (1.0 mmol) in dry THF (25 mL) a 1.0 M solution of potassium tert-butoxide (1.0 mmol) in dry THF was added dropwise and the mixture was stirred for 4 h. After filtration the solvent was removed in vacuo, the solid residue was washed with a cool ethanol (3 mL) and crystallised from ethanol.

Reference： [1]Guirado, Antonio; Alarcón, Enrique; Vicente, Yesica; Andreu, Raquel; Bautista, Delia; Gálvez, Jesús [Tetrahedron, 2016, vol. 72, # 27-28, p. 3922 - 3929]

45
[ 807331-41-5 ]
[ 6326-27-8 ]
4-dichloromethyl-2-(4-methylphenyl)-6-(2-naphthyl)pyrimidine [ No CAS ]
2-(4-methylphenyl)-4-(2-naphthyl)pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 73% 2: 5%	With potassium carbonate In acetonitrile for 12h; Reflux; Inert atmosphere;	7 One-pot general procedure for the synthesis of 2,4-diarylpyrimidines 7e-p General procedure: To a solution of 6 (1.0 mmol) in dry THF (25 mL) a 1.0 M solution of potassium tert-butoxide (1.0 mmol) in dry THF was added dropwise and the mixture was stirred for 4 h. After filtration the solvent was removed in vacuo, the solid residue was washed with a cool ethanol (3 mL) and crystallised from ethanol.

Reference： [1]Guirado, Antonio; Alarcón, Enrique; Vicente, Yesica; Andreu, Raquel; Bautista, Delia; Gálvez, Jesús [Tetrahedron, 2016, vol. 72, # 27-28, p. 3922 - 3929]

46
[ 1184912-94-4 ]
[ 6326-27-8 ]
4-(4-biphenylyl)-2-(4-methylphenyl)pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With potassium carbonate In acetonitrile for 12h; Reflux; Inert atmosphere;	10 One-pot general procedure for the synthesis of 2,4-diarylpyrimidines 7e-p General procedure: To a solution of 6 (1.0 mmol) in dry THF (25 mL) a 1.0 M solution of potassium tert-butoxide (1.0 mmol) in dry THF was added dropwise and the mixture was stirred for 4 h. After filtration the solvent was removed in vacuo, the solid residue was washed with a cool ethanol (3 mL) and crystallised from ethanol.

Reference： [1]Guirado, Antonio; Alarcón, Enrique; Vicente, Yesica; Andreu, Raquel; Bautista, Delia; Gálvez, Jesús [Tetrahedron, 2016, vol. 72, # 27-28, p. 3922 - 3929]

47
[ 6326-27-8 ]
[ 93-55-0 ]
[ 77232-22-5 ]

Yield	Reaction Conditions	Operation in experiment
86%	With ferrous(II) sulfate heptahydrate; 1,10-Phenanthroline; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In N,N-dimethyl-formamide at 120℃; for 12h; Sealed tube;	6 Example 6 Synthesis of 2- (4-methylphenyl) -4-phenylpyrimidine 0.3 mmol of 4-methylbenzamidine hydrochloride (0.0512 g), 0.75 mmol of phenylacetone (0.1006 g)0.03 mmol of ferrous sulfate heptahydrate (0.0083 g), 0.03 mmol of 1,10-phenanthroline (0.0054 g), tetramethylpiperidine nitrogenOxides (TEMPO) (0.0563 g) was added to a 10 mL tube reaction tube, and 2 mL of N, N-dimethylformamide (DMF) was added as a solvent,Sealed at 120 ° C for 12 hours. After the reaction, the reaction solution was passed through water, ethyl acetate, anhydrous sulfuric acidSodium drying and column chromatography (column chromatography separation conditions: the stationary phase of 300 ~ 400 mesh silica gel powder, the mobile phase ethyl acetate(A) and petroleum ether (B), the mobile phase change program (A: B) is 1: 50 → 1: 20, 0.0632 g of the reaction product (white solidbody). According to the characterization data, the obtained reaction product 2- (4-methylphenyl) -4-phenylpyrimidine pure (purity>95%), the structure is as follows:The product yield was calculated and the result was 86%.
86%	With ferrous(II) sulfate heptahydrate; 1,10-Phenanthroline; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; N,N-dimethyl-formamide at 120℃; for 12h; regioselective reaction;
78%	With [2,2]bipyridinyl; TEMPOL; copper diacetate; sodium acetate In 1,2-dichloro-benzene at 140℃; for 24h; Sealed tube;

Reference： [1]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN106496127, 2017, A Location in patent: Paragraph 0092; 0093; 0094; 0095; 0096; 0097; 0098
[2]Chu, Xue-Qiang; Cao, Wen-Bin; Xu, Xiao-Ping; Ji, Shun-Jun [Journal of Organic Chemistry, 2017, vol. 82, # 2, p. 1145 - 1154]
[3]Zhan, Jun-Long; Wu, Meng-Wei; Chen, Fei; Han, Bing [Journal of Organic Chemistry, 2016, vol. 81, # 23, p. 11994 - 12000]

48
(2S,3aR,5aR,5bS,9S,13S,14R,16aR,16bS)-4-bromo-13-[(2R,5S,6R)-5-(dimethylamino)-6-methyloxan-2-yl]oxy}-9-ethyl-14-methyl-2-[(2R,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyloxan-2-yl]oxy}-1H,2H,3H,3aH,4H,5H,5aH,5bH,6H,7H,9H,10H,11H,12H,13H,14H,15H,16aH,16bH-as-indaceno[3,2-d]oxacyclododecane-5,7,15-trione [ No CAS ]
[ 6326-27-8 ]
(1S,2R,8R,10S,12S,13R,17R,18S,22S)-18-[(2R,5S,6R)-5-(dimethylamino)-6-methyloxan-2-yl]oxy}-22-ethyl-17-methyl-5-(4-methylphenyl)-10-[(2R,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyloxan-2-yl]oxy}-23-oxa-4,6-diazapentacyclo[13.10.0.0²'¹³.0³'⁷.0^8,12]pentacosa-3⁽⁷⁾,4,14-triene-16,24-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12.6%	With potassium carbonate In acetonitrile at 85℃;	50 Example 50: (lS,2R,8R,10S,12S,13R,17R,18S,22S)-18-[(2R,5S,6R)-5-(dimethylamino)-6- methyloxan-2-yl]oxy}-22-ethyl-17-methyl-5-(4-methylphenyl)-10-[(2R,3R,4R,5S,6S)-3,4,5- trimethoxy-6-methyloxan-2-yl]oxy}-23-oxa-4,6- diazapentacyclo[13.10.0.0²'¹³.0³'⁷.0^{8 12}]pentacosa-3(7),4,14-triene-16,24-dione To a solution of Intermediate 1 (800 mg, 0.96 mmol) and 4-methyl-benzamidine hydrochloride (330 mg, 1.9 mmol) in acetonitrile (15 mL) was added potassium carbonate (400 mg, 2.9 mmol). The mixture was then heated to 85 °C overnight. The mixture was concentrated under reduced pressure to give an oil, which was purified by chromatography over silica gel (dichloromethane/methanol = 50/1 to 15/1) to give the crude product. The crude product was further purified by prep-HPLC to afford the title compound (105 mg, yield 12.6%) as a white solid. Partial 1H MR (400 MHz, CDC13): δ 1.70 (d, J= 8.0 Hz, 2H), 7.19 (d, J= 8.0 Hz, 2H), 6.71 (s, 1H), 4.91 (s, 1H), 4.80-4.74 (m, 1H), 4.43-4.39 (m, 2H), 3.98-3.92 (m, 1H), 3.65-3.61 (m, 1H), 3.37-3.33 (m, 1H), 3.26-3.22 (m, 2H), 3.13-3.09 (m, 1H), 2.75-2.62 (m, 3H), 2.01-1.85 (m, 5H), 0.85 (t, J= 7.2 Hz, 3H). LCMS: m/z 862.1 [M+H]+.

Reference： [1]Current Patent Assignee: AGRIMETIS LLC - WO2017/40882, 2017, A1 Location in patent: Page/Page column 80-81

49
[ 6326-27-8 ]
[ 104-81-4 ]
[ 17590-34-0 ]

Yield	Reaction Conditions	Operation in experiment
67%	With sulfur; lithium tert-butoxide In toluene at 140℃; for 12h; Schlenk technique; Inert atmosphere;	General procedure for the preparation of 1,2,4-thiadiazoles General procedure: A 20 mL of Schlenk tube equipped with a stir bar was charged with benzyl bromides (0.12 mmol), aryl amidines (0.1 mmol), S8 (0.1 mmol), LiOtBu (0.4 mmol). The tube was sealed with a Teflon lined cap, and the reaction mixture was stirred at 140 °C for 12 h in oil bath. Then the solvent was concentrated in vacuum and the residue was purified by flash column chromatography on silica gel with petroleum ether-EtOAc as the eluent to give the desired product.

Reference： [1]Zhou, Zhen; Liu, Miaochang; Sun, Song; Yao, En; Liu, Suqin; Wu, Zhiwen; Yu, Jin-Tao; Jiang, Yan; Cheng, Jiang [Tetrahedron Letters, 2017, vol. 58, # 26, p. 2571 - 2573]

50
[ 6326-27-8 ]
[ 100-52-7 ]
[ 536-74-3 ]
4,6-diphenyl-2-p-methylphenylpyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With copper(II) oxide; potassium hydroxide In N,N-dimethyl-formamide at 140℃; for 24h;	8 4,6-diphenyl-2- (p-tolyl) pyrimidine, comprising the steps of 0.3 mmol p-methylbenzamidine hydrochlorideand 0.39 mmol of benzaldehyde, 0.45 mmol of phenacetylene, and added thereto 0.03 mmol of Cu0, 0.9 mmol of K0H and 2-3 ml of DMF were added and stirred at 140 ° C for 24 hours to give the product; The product was extracted with ethyl acetate and dried to give the crude product. The crude product was purified by silica gel column chromatography (solvent volume ratio petroleum ether: ethyl acetate = 50: 1) To give 4,6-diphenyl-2- (p-tolyl) pyrimidine as a white solid. The yield was 88%

Reference： [1]Current Patent Assignee: ANHUI NORMAL UNIVERSITY - CN106632075, 2017, A Location in patent: Paragraph 0105-0108

51
[ 6326-27-8 ]
[ 613-92-3 ]
[ 3213-95-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium carbonate; copper(II) oxide In dimethyl sulfoxide at 110℃; for 18h;	4 Synthesis of 5- (4- (methyl) phenyl) -3- (phenyl) -1H-1,2,4-triazole, comprising the steps of: A, 0.5 mmol p-methylbenzamidine hydrochloride and 0.6 mmol N-hydroxyphenylcarboximide were placed in the reaction tube,And further adding 0.05 mmol of CuO,1.0 mmol Na2CO3 and 3 mL DMSO,The reaction was stirred at 110 ° C for 18 hours;B, the product was extracted with ethyl acetate,Dried over anhydrous sodium sulfate,Concentrated under reduced pressure,The crude product was purified by silica gel column chromatography (solvent volume ratio petroleum ether: ethyl acetate = 5: 1)(4- (methyl) phenyl) -3- (phenyl) -1H-1,2,4-triazole as a white solid,The yield was 90% and the melting point was 187-188 ° C.

Reference： [1]Current Patent Assignee: ANHUI NORMAL UNIVERSITY - CN106632106, 2017, A Location in patent: Paragraph 0076; 0077; 0078; 0079; 0080; 0081

52
[ 5033-28-3 ]
[ 6326-27-8 ]
5-(4-chlorophenyl)-3-(p-tolyl)-1H-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium carbonate; copper(II) oxide In dimethyl sulfoxide at 110℃; for 24h;	1 Synthesis of a 5- (4-chlorophenyl) -3- (p-tolyl) -1H-1,2,4-triazole comprising the steps of: A, take 0.5 mmol p-methylbenzamidine hydrochloride and0.6 mmol of 4-chloro-N-hydroxyphenylcarboximide in a reaction tube,And further adding 0.05 mmol of CuO, 1.0 mmol of K2CO3 and 3 mL of DMSO,The reaction was stirred at 110 ° C for 24 hours in air;B, the product was extracted with ethyl acetate,Dried over anhydrous sodium sulfate,Concentrated under reduced pressure to give the crude product,The crude product was purified by silica gel column chromatography (solvent volume ratio petroleum ether: ethyl acetate = 5: 1) to give a white solid,5- (4-chlorophenyl) -3- (p-tolyl) -1H-1,2,4-triazole in 80% yield and a melting point of 254 ° C.

Reference： [1]Current Patent Assignee: ANHUI NORMAL UNIVERSITY - CN106632106, 2017, A Location in patent: Paragraph 0058; 0059; 0060; 0061; 0062; 0063

53
[ 948-65-2 ]
[ 6326-27-8 ]
C₂₂H₁₇N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With copper(I) oxide; oxygen In 1-methyl-pyrrolidin-2-one at 80℃; for 4h; Sealed tube; Green chemistry;	2 Synthesis of 2-phenyl-4- (4-methylphenyl) -benzo [1,3,5] triazolidin-5-hydro-6-one 0.3 mmol of 4-methylbenzamidine hydrochloride (N. 2, corresponding compound, 0.0513 g) was weighed, 0.4 mmol of 2-phenyl-1-hydrogenindole (corresponding to (30) the corresponding compound, 0.0770 g) And 0.06 mmol cuprous oxide (0.0086 g) in 20 mL of test tubes, Plus 3mL N-methyl pyrrolidone as solvent, tube mouth closed with oxygen balloon, Stirring at 80 ° C for 4 hours; after completion of the reaction, The reaction solution was extracted with ethyl acetate, dried over anhydrous sodium sulfate and separated by column chromatography (column chromatography separation conditions: 300 ~ 400 mesh silica gel with mobile phase as ethyl acetate (viable) and petroleum ether (3) Phase change program (A: B) of 1: 6) to give 0.0808 g of the reaction product. According to the characterization data, The resulting reaction product was pure 2-phenyl-4- (4-methylphenyl) -benzo [1,3,5] triazolidin-5-hydro-6-one (purity> 95%) ; The product yield is calculated, the result is 81%.

Reference： [1]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN106946808, 2017, A Location in patent: Paragraph 0039; 0040; 0041; 0044

54
[ 6326-27-8 ]
[ 18465-11-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In water at 20℃; for 1h;	General procedure for synthesis of aryl amidines General procedure: A 100 mL flask was charged with 30 mL of anhydrous MeOH, 10 mmol of the arylnitrile, and 1.0 mmol of sodium methoxide. The complex was protected from moisture and stirred for 48 h. Then, 10 mmol of NH4Cl was added and stirring was continued for 24 h. Unreacted NH4Cl was filtered, and methanol was stripped from the filtrate to afford the product aryl amidine hydrochlorides, which was dissolved in 2.5 mL 8M sodium hydroxide aqueous solution and stirred for 1 h. Then chloroform (20 ml x 3) and H2O (20 ml x 3) were added successively to extract the product, and the combined organic layer was dried with anhydrous MgSO4 and then evaporated under vacuum to remove the organic solvent to give the desired arylamidine.

Reference： [1]Lu, Xiaodong; Xin, Xiaoyi; Wan, Boshun [Tetrahedron Letters, 2018, vol. 59, # 4, p. 361 - 364]

55
[ 21900-27-6 ]
[ 6326-27-8 ]
2-(3-bromo-5-chlorophenyl)-4,6-bis(4-methylphenyl)-1,3,5-triazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: 3-bromo-5-chlorobenzoic acid chloride; p-methylbenzamidine hydrochloride With triethylamine In 5,5-dimethyl-1,3-cyclohexadiene at 0 - 60℃; for 3.5h; Inert atmosphere; Stage #2: With 1,1,3,3-tetramethyldisilazane In 5,5-dimethyl-1,3-cyclohexadiene at 150℃; for 5h; Inert atmosphere;	24 Example 24 Under argon flow, 4-methylbenzamidine hydrochloride (512 mg, 3.0 mmol) was suspended in xylene (7.5 mL).The suspension was cooled to 0 ° C., triethylamine (420 μL, 3.0 mmol) and 3-bromo-5-chlorobenzoyl chloride (254 mg, 1.0 mmol) were added, and the mixture was stirred at 0 ° C. for 30 minutes and at 60 ° C. at 3 And stirred for a while.After allowing to cool, 1,1,3,3-tetramethyldisilazane (520 μL, 3.0 mmol) was added to the reaction mixture, and the mixture was stirred at 150 ° C. for 5 hours.After standing to cool, the low boiling point portion was distilled off from the reaction mixture under reduced pressure, water was added to the obtained residue, and the solid was filtered off.The solid was washed with water, methanol, then hexane.The obtained solid was dried under reduced pressure to obtain the objective 2- (3-bromo-5-chlorophenyl) -4,6-bis (4-methylphenyl) -1,3,5-triazine as a white solid ( 323 mg, 72%).

Reference： [1]Current Patent Assignee: TOSOH CORPORATION; SAGAMI CHEMICAL RESEARCH INSTITUTE - JP2018/30792, 2018, A Location in patent: Paragraph 0134-0135

56
[ 108-94-1 ]
[ 6326-27-8 ]
2-(p-methylphenyl)-1,3-diazaspiro[4,4]non-1-en-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With oxygen; sodium hydroxide In pyridine at 80℃; for 24h;
87%	With quinoline; oxygen; sodium hydroxide at 40℃; for 48h; Green chemistry;	2; 7 Example 2 Synthesis of 2-(p-methylphenyl)-1,3-diazaspiro[4,4]non-1-en-4-one A reaction tube was taken, and 0.9 mmol (36 mg) of sodium hydroxide, 0.2 mmol (34.1 mg) of 4-methylbenzene carboximidamide hydrochloride, 0.3 mmol (31.2 μL) of cyclohexanone, and 0.8 mL of quinoline were added under oxygen protection. The reaction was carried out at 40 ° C for 48 hours. The conventional treatment gave 39.7 mg of pure product with a yield of 87%.

Reference： [1]Xie, Yanjun; Cheng, Xiufang; Liu, Saiwen; Chen, Hui; Zhou, Wang; Yang, Luo; Deng, Guo-Jun [Green Chemistry, 2015, vol. 17, # 1, p. 209 - 213]
[2]Current Patent Assignee: XIANGTAN UNIVERSITY - CN104177298, 2018, B Location in patent: Paragraph 0086; 0111-0113; 0138

57
[ 110-18-9 ]
[ 6326-27-8 ]
[ 51721-68-7 ]
[ 39238-44-3 ]
2-(4-methoxyphenyl)-4-(p-tolyl)-1,3,5-triazine [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 2629 - 2633

58
1-(1H-benzo[f]chromen-2-yl)-2,2,2-trifluoroethan-1-one [ No CAS ]
[ 6326-27-8 ]
5-[(2-hydroxynaphthalen-1-yl)methyl]-2-(p-tolyl)-4-(trifluoromethyl)pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 6h; Reflux;	5-[(2-Hydroxynaphthalen-1-yl)methyl]-2-(n-tolyl)-4-(trifluoromethyl)pyrimidine (3j) General procedure: DBU (0.17 ml, 1.1 mmol) was added toa mixture of chromene 1 or 2 (1 mmol) and the respectiveamidine hydrochloride (1 mmol) in MeCN (5 ml), and theresulting solution heated under reflux for 6 h. The mixturewas cooled to room temperature, and poured with stirringinto cold water (20 ml). The formed precipitate was filteredoff, dried in air, and purified by recrystallization fromEtOH (compounds 3a-g,i-k) or from DMF-MeOH, 5:1mixture (compound 3h)

Reference： [1]Popova, Yulia V.; Sakhnenko, Darina V.; Arbuzova, Irina V.; Osyanin, Vitaly A.; Osipov, Dmitry V.; Klimochkin, Yuri N. [Chemistry of Heterocyclic Compounds, 2016, vol. 52, # 10, p. 803 - 808][Khim. Geterotsikl. Soedin., 2016, vol. 52, # 10, p. 803 - 808]

59
1-(6,7-dimethyl-4H-chromen-3-yl)-2,2,2-trifluoroethan-1-one [ No CAS ]
[ 6326-27-8 ]
5-(2-hydroxy-4,5-dimethylbenzyl)-2-(p-tolyl)-4-(trifluoromethyl)pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 6h; Reflux;	5-(2-Hydroxy-4,5-dimethylbenzyl)-2-(p-tolyl)-4-(trifluoromethyl)pyrimidine (3d) General procedure: DBU (0.17 ml, 1.1 mmol) was added toa mixture of chromene 1 or 2 (1 mmol) and the respectiveamidine hydrochloride (1 mmol) in MeCN (5 ml), and theresulting solution heated under reflux for 6 h. The mixturewas cooled to room temperature, and poured with stirringinto cold water (20 ml). The formed precipitate was filteredoff, dried in air, and purified by recrystallization fromEtOH (compounds 3a-g,i-k) or from DMF-MeOH, 5:1mixture (compound 3h)

60
[ 104-87-0 ]
[ 6326-27-8 ]
[ 6726-45-0 ]

Yield	Reaction Conditions	Operation in experiment
68%	With copper(II) acetate monohydrate; sodium carbonate In toluene at 100℃; for 24h;	General Procedure for the Preparation 7a-7x General procedure: A mixture ofaldehyde 1 (6.8 mmol), amidine hydrochloride 2 (2 g,11.4 mmol), Na2CO3 (1.21 g, 11.4 mmol, 1.0 equiv) andCu(OAc)2 (10 mol%) was stirred in toluene (20 mL) under100 °C in air for 24 h. After completion of the reaction, themixture was cooled to room temperature. The water wasadded to the reaction system and atmospheric distillation untiltoluene was evaporated. The resulting solution was filteredand residue with hot water washed 3 times. The crude productwas purified by column chromatography on silica gel usingpetroleum ether/EtOAc (100:1) as an eluent to give the correspondingproducts 7a-7x.

Reference： [1]Wang, Xueding; Xu, Yilian; Yang, Lu; Lu, Xiang; Zou, Hao; Yang, Weiqing; Zhang, Yuanyuan; Li, Zicheng; Ma, Menglin [Journal of Fluorescence, 2018, vol. 28, # 2, p. 707 - 723]

61
[ 6326-27-8 ]
[ 100-52-7 ]
[ 7753-06-2 ]

Yield	Reaction Conditions	Operation in experiment
78%	With copper(II) acetate monohydrate; sodium carbonate In toluene at 100℃; for 24h;	General Procedure for the Preparation 7a-7x General procedure: A mixture ofaldehyde 1 (6.8 mmol), amidine hydrochloride 2 (2 g,11.4 mmol), Na2CO3 (1.21 g, 11.4 mmol, 1.0 equiv) andCu(OAc)2 (10 mol%) was stirred in toluene (20 mL) under100 °C in air for 24 h. After completion of the reaction, themixture was cooled to room temperature. The water wasadded to the reaction system and atmospheric distillation untiltoluene was evaporated. The resulting solution was filteredand residue with hot water washed 3 times. The crude productwas purified by column chromatography on silica gel usingpetroleum ether/EtOAc (100:1) as an eluent to give the correspondingproducts 7a-7x.

Reference： [1]Wang, Xueding; Xu, Yilian; Yang, Lu; Lu, Xiang; Zou, Hao; Yang, Weiqing; Zhang, Yuanyuan; Li, Zicheng; Ma, Menglin [Journal of Fluorescence, 2018, vol. 28, # 2, p. 707 - 723]

62
[ 6326-27-8 ]
[ 1493-27-2 ]
[ 120-03-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate; copper(I) bromide In dimethyl sulfoxide at 120℃; for 8h;	Synthesis of benzimidazole derivatives 3a-h General procedure: A mixture of 1-fluoro-2-nitrobenzene (1) (0.141 g,1.0 mmol), the appropriate benzamidine hydrochloride 2a-h (1.0 mmol), CuBr (0.029 g, 0.2 mmol), and K2CO3 (0.276 g,2.0 mmol) in dry DMSO (3.0 ml) was heated in a round bottom flask for 8 h at 120°C. After the reaction was complete (TLC), the mixture was cooled, quenched with water (20 ml), and extracted with EtOAc (3 × 20 ml). The extract was washed with 20% aqueous NaCl solution, dried over Na2SO4, and concentrated under reduced pressure.The residue was purified by column chromatography using petroleum ether - ethyl acetate, 4:1, as eluent to afford the pure products.

Reference： [1]Sayahi, Mohammad Hosein; Khoshneviszadeh, Mehdi; Soheilizad, Mehdi; Saghanezhad, Seyyed Jafar; Mahdavi, Mohammad [Chemistry of Heterocyclic Compounds, 2018, vol. 54, # 3, p. 351 - 354][Khim. Geterotsikl. Soedin., 2018, vol. 54, # 3, p. 351 - 354,4]

63
[ 91-56-5 ]
[ 6326-27-8 ]
2-(4,6-di-p-tolyl-1,3,5-triazin-2-yl)aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 25℃; for 24h; Sealed tube;
60%	With potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 20℃; for 5h;	6 Synthesis of 2-(4,6-di-p-tolyl-1,3,5-triazin-2-yl)aniline: The specific steps are as follows: adding blush (44.1 mg, 0.3 mmol) to p-methylbenzamide hydrochloride (153.5 mg,0.9 mmol), CuI (5.7 mg, 0.03 mmol) and potassium phosphate (381.6 mg, 1.8 mmol), added to 3 mL of DMSO, magnetic at room temperatureAfter stirring for 5 hours, the reaction mixture was extracted with methylene chloride.After that, the solvent is distilled off under reduced pressure to obtain a crude product, and the crude product is subjected to column separation using dichloromethane/petroleum ether = 1:20 (V/V) as eluent.Purification is the desired product. The product is a yellow solid with a yield of 60%.

Reference： [1]Jia, Feng-Cheng; Xu, Cheng; Wang, Yu-Wei; Chen, Zhi-Peng; Chen, Yun-Feng; Wu, An-Xin [Organic and Biomolecular Chemistry, 2018, vol. 16, # 23, p. 4223 - 4226]
[2]Current Patent Assignee: WUHAN INSTITUTE OF TECHNOLOGY - CN108558782, 2018, A Location in patent: Paragraph 0031

64
[ 13323-81-4 ]
[ 6326-27-8 ]
[ 873-76-7 ]
4-(4-chlorophenyl)-6-phenyl-2-p-tolylpyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With copper diacetate; potassium hydroxide In toluene at 120℃; for 24h;	8A; 8B Synthesis of 4-(4-chlorophenyl)-6-phenyl-2-p-tolylpyrimidine, including the following steps: A, 0.3 mmol p-methylbenzylamidine hydrochloride and 0.39 mmol 4-chlorobenzyl alcohol, 0.45 mmol 1-phenylethanol,Further, 0.03 mmol of Cu(OAc) 2, 0.9 mmol of KOH, and 3 mL of toluene were added.The reaction was stirred at 120 ° C for 24 hours to obtain a product;B. The product is extracted with ethyl acetate and dried to give a crude product.The crude product was chromatographed on silica gel to petroleum ether:Ethyl acetate = 50:1 as the eluent, which was purified to give 4-(4-chlorophenyl)-6-phenyl-2-p-tolylpyrimidine as a white solid.The yield was 71% and the melting point was 188-190 °C.

Reference： [1]Current Patent Assignee: ANHUI NORMAL UNIVERSITY - CN108409672, 2018, A Location in patent: Paragraph 0105-0108

65
[ 6326-27-8 ]
[ 88-65-3 ]
[ 18818-41-2 ]

Yield	Reaction Conditions	Operation in experiment
76%	With 8-quinolinol; sodium hydroxide; copper dichloride In water at 20℃; for 0.333333h; Sealed tube; Microwave irradiation;	Experimental General procedure: In a 10 mL glass tube 2-iodobenzoic acid (1.0 mmol), acetamidine hydrochloride (1.2 mmol), CuCl2 (0.1 mmol), L2 (0.1 mmol), and NaOH (4.0 equiv.) and 3.0 mL water were placed. The vessel was then sealed with a septum and placed into the microwave cavity. Initial microwave irradiation of 120 W by using a CEM Discover microwave synthesizer was used at the room temperature for 20 min. The reaction mixture was stirred continuously during the reaction. After completion of the reaction, the solvent was removed in vacuo. The residue was purified by silica gel column chromatography to afford the corresponding product. All the products were confirmed by NMR and MS spectroscopic analysis.

Reference： [1]Ke, Fang; Liu, Caiqin; Zhang, Peng; Xu, Jianhua; Chen, Xiaole [Synthetic Communications, 2018, vol. 48, # 24, p. 3089 - 3098]

66
[ 75-09-2 ]
[ 6326-27-8 ]
[ 51721-68-7 ]
[ 39238-44-3 ]
2-(4-methoxyphenyl)-4-(p-tolyl)-1,3,5-triazine [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 1166 - 1170

67
[ 1895-39-2 ]
[ 6326-27-8 ]
[ 39238-44-3 ]

Yield	Reaction Conditions	Operation in experiment
76%	With caesium carbonate In acetonitrile at 120℃; for 24h;	9 The reaction bottle by adding 1 b (4 mmol), two chlorofluorcarbons sodium acetate (4 mmol), cesium carbonate (8 mmol) and acetonitrile (10 ml), then in 120 °C heating reaction 24 hours. After the reaction is finished using water quenching, and then the extraction of ethyl acetate, the combined organic phase after drying with anhydrous sodium sulfate, concentrated using petroleum ether and ethyl acetate mixed solvent of column chromatography to obtain the product 3 b, yield is 76%. White solid
76%	With caesium carbonate In acetonitrile at 120℃; for 24h; Schlenk technique;

Reference： [1]Current Patent Assignee: ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY - CN109810069, 2019, A Location in patent: Paragraph 0043-0045
[2]Yan, Yizhe; Cui, Chang; Wang, Jianyong; Li, Shaoqing; Tang, Lin; Liu, Yanqi [Organic and Biomolecular Chemistry, 2019, vol. 17, # 35, p. 8071 - 8074]

68
[ 667-27-6 ]
[ 6326-27-8 ]
[ 51721-68-7 ]
[ 39238-44-3 ]
2-(4-methoxyphenyl)-4-(p-tolyl)-1,3,5-triazine [ No CAS ]

Reference： [1]Chemical Communications,2019,vol. 55,p. 8079 - 8082

69
[ 1846-68-0 ]
[ 6326-27-8 ]
C₁₆H₂₀N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With potassium carbonate In dichloromethane at 20℃; for 3h;	General procedure for heterogeneous Au(I)-catalyzed synthesis of pyrimidines General procedure: A mixture of ynal 1 (0.5 mmol), amidine hydrochloride 2 (0.6 mmol), K2CO3(1.0 mmol), and MCM-41-PPh3-AuCl (41 mg, 0.015 mmol) in DCM (3mL) was stirred at room temperature for 3 h (TLC monitored). The resulting mixture was then diluted with ethyl acetate (15 mL) and filtered. The gold catalyst was washed with distilled water(5 mL), and dry ethanol (25mL) and reused in the next run. The filtrate was concentrated under reduced pressure and the residue was purified by chromatography on silicagel (eluent: petroleum ether/ethyl acetate) to afford the desired product 3.

Reference： [1]Jiang, Minhua; Nie, Quan; Cai, Mingzhong [Synthetic Communications, 2019, vol. 49, # 19, p. 2488 - 2500]

70
[ 2975-46-4 ]
[ 6326-27-8 ]
[ 77232-13-4 ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium carbonate; In dichloromethane; at 20℃; for 3h;	General procedure: A mixture of ynal 1 (0.5 mmol), amidine hydrochloride 2 (0.6 mmol), K2CO3(1.0 mmol), and MCM-41-PPh3-AuCl (41 mg, 0.015 mmol) in DCM (3mL) was stirred at room temperature for 3 h (TLC monitored). The resulting mixture was then diluted with ethyl acetate (15 mL) and filtered. The gold catalyst was washed with distilled water(5 mL), and dry ethanol (25mL) and reused in the next run. The filtrate was concentrated under reduced pressure and the residue was purified by chromatography on silicagel (eluent: petroleum ether/ethyl acetate) to afford the desired product 3.

Reference： [1]Synthetic Communications,2019,vol. 49,p. 2488 - 2500

71
[ 6326-27-8 ]
[ 100-44-7 ]
[ 50483-75-5 ]

Yield	Reaction Conditions	Operation in experiment
51%	With sulfur; sodium carbonate In dimethyl sulfoxide at 120℃; for 24h; Sealed tube;	General procedure: A mixture of benzamidine hydrochloride (1.0 mmol), benzyl chloride (0.5 mmol), sulfur powder (2.5 mmol),Na2CO3 (2.0 mmol) and dimethyl sulfoxide (2.0 mL) was placed in a sealed pressure vessel (25 mL) containing a magnetic stirring bar. The tube was capped and stirred in a preheated oil bath at 120 °C for 24 h. After the mixture was cooled to room temperature, the resulting solution was diluted with ethyl acetate (25 mL) and extracted with ethyl acetate (3 × 10 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered. The filtrate was concentrated, and the residue was purified by column chromatography on SiO2 (petroleum ether / dichloromethane, 30:1 to 10:1) to give 1,2,4-thiadiazoles (60 % yield) and 1,3,5-triazines (15% yield) .

Reference： [1]Zhang, Yurong; Liu, Yafei; Zhang, Jun; Gu, Ren; Han, Shiqing [Tetrahedron Letters, 2019, vol. 60, # 49]

72
[ 6326-27-8 ]
[ 51721-68-7 ]
[ 298-12-4 ]
[ 39238-44-3 ]
2-(4-methoxyphenyl)-4-(p-tolyl)-1,3,5-triazine [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2019,vol. 2019,p. 7800 - 7803

73
[ 6326-27-8 ]
[ 103-72-0 ]
[ 80-70-6 ]
N2,N2-dimethyl-N4-phenyl-6-(p-tolyl)-1,3,5-triazine-2,4-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With tert.-butylhydroperoxide In dimethyl sulfoxide at 25℃; for 0.166667h;	21 Add 13.5 mg of phenyl isothiocyanate to 1 mL of dimethyl sulfoxide,Tetramethylguanidine 11.5mg, then add 4-methylbenzamidine hydrochloride 17.0mg,Rabbit hemoglobin (0.5mol), slowly add three times the amount of tert-butyl hydroperoxide and react at 25°C (normal temperature) for ten minutes, and then use thin-layer chromatography to detect the progress of the reaction;Then water was added to quench the reaction, extracted with ethyl acetate and dried by adding anhydrous sodium sulfate,Concentrate, then use silica gel column chromatography (ethyl acetate/hexane) for further purification,28.1 mg of N2,N2-dimethyl-N4-phenyl-6-(p-tolyl)-2,4-diamino-1,3,5-triazine was obtained, with a yield of 92%, and a white solid.
40%	With rose bengal In ethanol; dichloromethane at 20℃; for 12h; Irradiation;

Reference： [1]Current Patent Assignee: JILIN UNIVERSITY - CN111606865, 2020, A Location in patent: Paragraph 0225-0231
[2]Guo, Wei; Zhao, Mingming; Du, Chengtang; Zheng, Lvyin; Li, Luo; Chen, Liping; Tao, Kailiang; Tan, Wen; Xie, Zhen; Cai, Liuhuan; Fan, Xiaolin; Zhang, Kai [Journal of Organic Chemistry, 2019]

74
potassium (Z)-2-cyano-2-fluoroethenolate [ No CAS ]
[ 6326-27-8 ]
5-fluoro-2-(4-methylphenyl)pyrimidine-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	In methanol at 20℃; for 16h; Inert atmosphere; Schlenk technique;	General Procedure for the synthesis of pyrimidine-derivatives from amidine hydrochlorides General procedure: The amidine hydrochloride (2.0 eq) and potassium-(Z)-2-cyano-2-fluoroethenolate (8) were suspended in dry methanol (15 mL) under argon atmosphere. The reaction mixture was stirred for 16 h at room temperature, all volatiles were removed in vacuo and the residue was taken up in water and ethyl acetate. The aqueous phase was extracted three times with ethyl acetate, washed with brine, dried over sodium sulfate and the solvent was removed in vacuo. The crude product was purified by column chromatography (cHex/EtOAc, Isolera Flash Purification System, gradient from 0 to 100% EtOAc).

Reference： [1]Dietz, Jule-Philipp; Lucas, Tobias; Opatz, Till [Beilstein Journal of Organic Chemistry, 2020, vol. 16, p. 445 - 450]

75
[ 6326-27-8 ]
[ 614-47-1 ]
4,6-diphenyl-2-p-methylphenylpyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium hydroxide In ethanol at 20℃; Reflux;	Pyrimidines 3a-3c (general procedure). General procedure: A mixtureof 0.01 mol of amidine hydrochloride 2a-2c, 0.01 molof (E)-1-aryl-3-phenylprop-2-en-1-one 3a-3c, and1.12 g (0.02 mol) of KOH in 30 mL of absolute ethanolwas left to stand overnight at room temperature and thenrefl uxed for 3 h, and the solvent was evaporated. Theresidue was poured with 50 mL of water, left to standfor 3 h in the cold, and the precipitate was fi ltered off.4,6-Diphenyl-2-(p-tolyl)pyrimidine (3a) was preparedfrom 4-methylbenzamidine hydrochloride [13]and (E)-N,1-diphenylmethanimine (4a). Yield 65.0%,mp 188-190°, Rf 0.62. IR spectrum, ν, cm-1: 1605,1595 (C=C-C=N). 1H NMR spectrum (DMSO-d6-CCl4,1 : 3), δ, ppm: 2.47 s (3H, CH3), 7.27-7.32 m (2H, H3',5',C6H4), 7.48-7.58 m (6H, 2H3',4',5', C6H5), 8.24 s (1H,H5pyrimidine), 8.34-8.42 m (4H, 2H2',6', C6H5), 8.54-8.59 m(2H, H2',6', C6H4). 13C NMR spectrum, δ, ppm: 21.0(CH3), 109.5, 126.9, 127.8, 128.1, 128.4, 130.0, 134.9,136.8, 139.6, 163.4, 163.7. Found, %: C 85.54; H 5.77;N 8.45. C23H18N2. Calculated, %: C 85.68; H 5.63; N8.69.

Reference： [1]Danagulyan, G. G.; Gukasyan, G. T.; Harutyunyan, A. A.; Panosyan, H. A.; Safaryan, M. S. [Russian Journal of Organic Chemistry, 2020, vol. 56, # 2, p. 269 - 275][Zh. Org. Khim., 2020, vol. 56, # 2, p. 269 - 276,8]

76
[ 103-82-2 ]
[ 6326-27-8 ]
[ 50483-75-5 ]

Yield	Reaction Conditions	Operation in experiment
63%	With sulfur; copper(l) iodide; sodium carbonate In dimethyl sulfoxide at 130℃; for 24h;	16 Preparation method: In a 25mL pressure tube, add 0.5mmol 4-methylbenzamidine hydrochloride, 1.0mmol phenylacetic acid, 3.0mmol sulfur powder, 1.0mmol Na2CO3, 0.1mmol CuI,Then add 2mL of dimethyl sulfoxide and stir at 130 ° C for 24 hours. The TLC plate detects that the reaction is complete and a product is formed.The reaction solution was cooled, extracted, dried, evaporated under reduced pressure, filtered by column chromatography, and filtered to obtain a white solid.The yield was 63%.
63%	With sulfur; copper(l) iodide; sodium carbonate In dimethyl sulfoxide at 130℃; for 24h; Inert atmosphere;

Reference： [1]Current Patent Assignee: NANJING TECH UNIVERSITY - CN111018807, 2020, A Location in patent: Paragraph 0113-0118
[2]Liu, Yafei; Zhang, Yurong; Zhang, Jun; Hu, Liang; Han, Shiqing [Tetrahedron Letters, 2021, vol. 65]

77
C₂₁H₁₅BrO [ No CAS ]
[ 6326-27-8 ]
4-biphenyl-3-yl-6-(4-bromophenyl)-2-p-tolylpyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40.28%	With sodium hydroxide In ethanol; toluene at 80℃;	2 1-Biphenyl-3-yl-3-(4-bromo-phenyl)-propenone (51 g, 140.4 mmole), 4-methylbenzamidine hydrochloride (26.35 g, 154.44 mmole) with sodium hydroxide (8.42 g, 210.6 mmole), 77 ml of toluene, and 255 ml of ethanol were added in a reaction flask; heating and stirring was initiated, and the mixture was maintained at 80° C. for reflux. After the reaction was completed, the reaction was cooled to 60° C. 100 ml of deionized water was added. After stirring for 5 minutes, the aqueous layer was removed, the organic layer was concentrated until solids were precipitated. After being washed with ethyl acetate, filtered and dried, a white solid (about 27 g) was obtained in a yield of 40.28%.

Reference： [1]Current Patent Assignee: E-RAY OPTOELECTRONICS TECHNOLOGY CO., LTD. - US2020/127211, 2020, A1 Location in patent: Paragraph 0066-0068

78
C₂₁H₁₅BrO [ No CAS ]
[ 6326-27-8 ]
4-biphenyl-3-yl-6-(3-bromophenyl)-2-p-tolylpyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39.6%	With sodium hydroxide In ethanol; toluene at 80℃;	1 1-Biphenyl-3-yl-3-(3-bromo-phenyl)-propenone (52 g, 143.15 mmole), 4-methylbenzamidine hydrochloride (26.87 g, 157.47 mmole) and sodium hydroxide (8.56 g, 214.73 mmole), 78 ml of toluene, 260 ml of ethanol were placed in a reaction flask, and heating and stirring was initiated. The mixture was maintained at 80° C. for reflux. After the reaction was completed, the reaction was cooled to 60° C., 100 ml of deionized water was added and stirred for 5 minutes. An aqueous layer was removed. An organic layer was concentrated until solids were precipitated. After washing with ethyl acetate, filtered and dried again, a white solid (about 27.7 g) was obtained with a yield of 39.6%.

Reference： [1]Current Patent Assignee: E-RAY OPTOELECTRONICS TECHNOLOGY CO., LTD. - US2020/127211, 2020, A1 Location in patent: Paragraph 0061-0063

79
[ 6326-27-8 ]
[ 100-52-7 ]
[ 121-44-8 ]
[ 77232-22-5 ]

Yield	Reaction Conditions	Operation in experiment
88%	With di-tert-butyl peroxide; iodine In chlorobenzene at 150℃; for 8h;
88%	With di-tert-butyl peroxide; iodine In chlorobenzene at 150℃; for 8h; Sealed tube;	15 Example 15 Add 1b (85.3mg, 0.5mmol), 2a (53mg, 0.5mmol), 3a (101mg, 1.0mmol), di-tert-butyl peroxide (73mg, 0.5mmol), elemental iodine (25.4mg) to a 35mL sealed tube , 0.2mmol) and chlorobenzene (2mL), then placed in a 150°C oil bath and stirred for 8h. The reaction was quenched by adding 50 mL of water, extracted with ethyl acetate (50 mL×3), and then the organic phase was washed with 10% Na2S2O3 solution and saturated brine in turn, and dried over anhydrous sodium sulfate. It was filtered, spin-dried, and separated by silica gel column (petroleum ether/ethyl acetate=100/1) to obtain the target product 4ab (108.2 mg, 88%).

Reference： [1]Gao, Qinghe; Wu, Manman; Zhang, Ke; Yang, Ning; Liu, Mengting; Li, Juan; Fang, Lizhen; Bai, Suping; Xu, Yongtao [Organic Letters, 2020, vol. 22, # 14, p. 5645 - 5649]
[2]Current Patent Assignee: XINXIANG MEDICAL UNIVERSITY - CN111362880, 2020, A Location in patent: Paragraph 0042-0044

80
[ 121194-34-1 ]
[ 6326-27-8 ]
4-fluoro-2,6-di-p-tolylpyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With potassium hydrogencarbonate In 1,4-dioxane at 60℃; for 48h;	Synthesis of 2,6-Disubstituted 4-Fluoropyrimidines 3a-m and 4a-o; General Procedure General procedure: To a round-bottom flask (10 mL) with a magnetic stirrer bar, 1,4-dioxane(3.0 mL), -CF3-aryl ketone (0.30 mmol, 1.0 equiv), amidine hydrochloride(0.33 mmol, 1.1 equiv) and KHCO3 (0.9 mmol, 3.0 equiv)were added. The resulting mixture was stirred at 60 °C for 12-48 hand the progress of the reaction was monitored by TLC. After the consumptionof -CF3-aryl ketone, the reaction was quenched with H2O(10 mL), and the mixture was extracted with EtOAc (3 × 10 mL). Theorganic layer was then dried over anhydrous Na2SO4 and concentratedunder vacuum by rotary evaporation. The residue was purified bychromatography on silica gel (PE/EtOAc) to afford the desired compound.

Reference： [1]Liu, Fangran; Qian, Qun; Yang, Chunhao; Zhang, Xiaofei [Synthesis, 2020, vol. 52, # 2, p. 273 - 280]

81
C₁₄H₁₁ClO₄ [ No CAS ]
[ 6326-27-8 ]
ethyl 2-[9-chloro-2-(p-tolyl)-5H-chromeno[4,3-d]pyrimidin-5-yl]acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: p-methylbenzamidine hydrochloride With base In ethanol for 0.166667h; Stage #2: C₁₄H₁₁ClO₄ In ethanol at 20℃; for 5h;	Chromeno[4,3-d]pyrimidines 8a-aa; General Procedure General procedure: Commercially available amidine hydrochloride 2a-h·HCl (2.4 mmol) and an equimolar amount of strong base (NaOH, NaOEt, or DBU) were mixed in EtOH (95%, 10 mL). The mixture was stirred for 10 min and then 3-vinylchromone 7a-t (2 mmol) was added and the mixture was further stirred at rt. The end of the reaction was determined by TLC (hexane/EtOAc, 7:3). The mixture was poured into water (100 mL) containing concd HCl (1 mL), and the precipitate formed was collected by filtration, washed with water, and dried. The crude product was crystallized (hexane or hexane/EtOAc).

Reference： [1]Chernov, Nikita M.; Potapova, Anastasia E.; Shutov, Roman V.; Yakovlev, Igor P. [Synthesis, 2020, vol. 52, # 1, p. 40 - 50]

82
[ 14802-30-3 ]
[ 6326-27-8 ]
[ 71103-77-0 ]

Yield	Reaction Conditions	Operation in experiment
77.4%	With potassium hydroxide In ethanol for 5h; Reflux;	2,4,6-Trisubstituted pyrimidines 3 (general procedure). General procedure: A mixture of 0.01 mol of amidine hydrochloride1 and 0.01 mol of (E)-1,3-diarylprop-2-en-1-one 2[10], and 1.12 g (0.02 mol) of KOH in 40 mL of ethanolwas heated under refl ux for 5 h, after which the solventwas removed, the residue was poured with 40 mL ofwater, and the product that precipitated was fi ltered offand recrystallized from 80% AcOH. 2,4-Bis(4-methylphenyl)-6-phenylpyrimidine(3a) was prepared from compound benzamidine hydrochloride(1b) and (E)-1-(4-methylphenyl)-3-phenylprop-2-en-1-one (2a). Yield 2.6 g (77.4%), mp 180-182°C, Rf 0.72. IR spectrum, ν, cm-1: 1611, 1586(C=C-C=N). 1H NMR spectrum, δ, ppm: 2.47 br.s (6H,2CH3), 7.27-7.31 m (2H, H3,5, 2-C6H4), 7.31-7.35 m(2H, H3,5, 4-C6H4), 7.48-7.57 m (3H, H3,4,5, 6-C6H5),8.18 s (1H, H5pyrimidine), 8.25-8.30 m (2H, H2,6, 4-C6H4),8.34-8.39 m (2H, H2,6, 6-C6H5), 8.53-8.57 m (2H, H2,6,2-C6H5). 13C NMR spectrum, δ, ppm: 20.9 (CH3), 21.0(CH3), 109.1 (CH), 126.78 (2CH), 126.83 (2CH), 127.8(2CH), 128.1 (2CH), 128.4 (2CH), 128.8 (2CH), 130.0(CH), 134.1, 135.0, 136.9, 139.5, 140.0, 163.3, 163.6,163.7. Found, %: C 85.43; H 6.24; N 8.17. C24H20N2.Calculated, %: C 85.68; H 5.99; N 8.33.

Reference： [1]Harutyunyan; Panosyan; Danagulyan [Russian Journal of Organic Chemistry, 2020, vol. 56, # 11, p. 1952 - 1957][Zh. Org. Khim., 2020, vol. 56, p. 1748 - 1754,6]

83
[ 6326-27-8 ]
[ 103-72-0 ]
C₁₅H₁₅N₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In methanol at 20℃;	General procedure for 3,5-disubstituted 1,2,4-thiadiazoles 2 General procedure: In an oven-dried single-necked bottle (10 mL) equipped with a stir bar, amidine hydrochloride (0.2 mmol), isothiocyanate 2 (0.2 mmol), NEt3 (0.4 mmol), and CH3OH (2 mL) were added and stirred at room temperature until the conversion was completed as indicated by TLC. Then, rhodamine 6G (0.5 mol %) was added, the reaction mixture was open to the air and stirred at room temperature under the irradiation of a 18 W LED lamp for 8 h. After completion of the reaction, the resulting mixture was extracted with EtOAc and the organic phase was then removed under vacuum. The residue was purified by flash column chromatography using a mixture of petroleum ether and ethyl acetate as eluent to give the desired products 2.Compounds 2a-x are known compounds and their spectral data are in agreement with those reported in the literature (see also the Supplementary Material file)
	In dichloromethane at 20℃; Alkaline conditions;

Reference： [1]Chen, Junmin; Sheng, Shouri; Xiong, Zhiqiang; Zhong, Qihao [Arkivoc, 2021, vol. 2021, # 8]
[2]Cao, Xian-Ting; Zheng, Zuo-Ling; Liu, Jie; Hu, Yu-He; Yu, Hao-Yun; Cai, Shasha; Wang, Guannan [Advanced Synthesis and Catalysis, 2022, vol. 364, # 3, p. 689 - 694]

84
[ 6326-27-8 ]
[ 622-59-3 ]
C₁₆H₁₇N₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In methanol at 20℃;	General procedure for 3,5-disubstituted 1,2,4-thiadiazoles 2 General procedure: In an oven-dried single-necked bottle (10 mL) equipped with a stir bar, amidine hydrochloride (0.2 mmol), isothiocyanate 2 (0.2 mmol), NEt3 (0.4 mmol), and CH3OH (2 mL) were added and stirred at room temperature until the conversion was completed as indicated by TLC. Then, rhodamine 6G (0.5 mol %) was added, the reaction mixture was open to the air and stirred at room temperature under the irradiation of a 18 W LED lamp for 8 h. After completion of the reaction, the resulting mixture was extracted with EtOAc and the organic phase was then removed under vacuum. The residue was purified by flash column chromatography using a mixture of petroleum ether and ethyl acetate as eluent to give the desired products 2.Compounds 2a-x are known compounds and their spectral data are in agreement with those reported in the literature (see also the Supplementary Material file)

Reference： [1]Chen, Junmin; Sheng, Shouri; Xiong, Zhiqiang; Zhong, Qihao [Arkivoc, 2021, vol. 2021, # 8]

85
[ 2253-73-8 ]
[ 6326-27-8 ]
C₁₂H₁₇N₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In methanol at 20℃;	General procedure for 3,5-disubstituted 1,2,4-thiadiazoles 2 General procedure: In an oven-dried single-necked bottle (10 mL) equipped with a stir bar, amidine hydrochloride (0.2 mmol), isothiocyanate 2 (0.2 mmol), NEt3 (0.4 mmol), and CH3OH (2 mL) were added and stirred at room temperature until the conversion was completed as indicated by TLC. Then, rhodamine 6G (0.5 mol %) was added, the reaction mixture was open to the air and stirred at room temperature under the irradiation of a 18 W LED lamp for 8 h. After completion of the reaction, the resulting mixture was extracted with EtOAc and the organic phase was then removed under vacuum. The residue was purified by flash column chromatography using a mixture of petroleum ether and ethyl acetate as eluent to give the desired products 2.Compounds 2a-x are known compounds and their spectral data are in agreement with those reported in the literature (see also the Supplementary Material file)

Reference： [1]Chen, Junmin; Sheng, Shouri; Xiong, Zhiqiang; Zhong, Qihao [Arkivoc, 2021, vol. 2021, # 8]

86
[ 6326-27-8 ]
[ 103-72-0 ]
[ 100-63-0 ]
C₂₁H₁₈N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With potassium carbonate In toluene at 30℃; for 12h;	2 Preparation method: add 0.1mmol of 4-methylbenzamidine hydrochloride, 0.1mmol of phenyl isothiocyanate, 0.15mmol of phenylhydrazine, 0.2mmol of potassium carbonate and 1.0mL of toluene into the reaction tube, and mix them. The reaction was stirred at 30°C for 12 hours. After the reaction, the reaction was separated and purified by column chromatography. The volume ratio of petroleum ether and ethyl acetate in the column chromatography eluent was 5:1 to obtain the purified target product. The yield was 72%, the purity is 99.9%.

Reference： [1]Current Patent Assignee: UNIV GANNAN NORMAL - CN113480486, 2021, A Location in patent: Paragraph 0109-0117

87
[ 6972-27-6 ]
[ 6326-27-8 ]
N-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)-4-methylbenzimidamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In <i>tert</i>-butyl alcohol at 80℃; for 24h; Sealed tube; Inert atmosphere;	General procedure for the preparation of N-uracil amidines from 6-chlorouracil General procedure: The 1,3-dimethyl-6-chlorouracil (349 mg, 2 mmol, 1.0 eq.), benzamidine hydrochloride (3.0 mmol, 1.5 equiv.), 1,8-diazabicyclo[5.4.0]undec-7-ene (660 mL, 4.4 mmol, 2.2 equiv.) were taken in an oven-dried pressure vial (10 mL). In this mixture, anhydrous tert-butanol (0.5 mL) was added using a syringe. The vessel was flushed with N2 and then sealed with a septum. The resulting mixture was placed in a preheated oil bath at 80°C and stirred for 24 hours. The reaction mixture was extracted with ethyl acetate (3 x 15 mL), and the combined ethyl acetate was washed with water (20 mL). The organic layer was dried over Na2SO4, filtered, concentrated under reduced pressure. The resulting crude product was purified by column chromatography using ethyl acetate/petroleum ether mixture as eluent

Reference： [1]Debnath, Pradip [Synthetic Communications, 2022, vol. 52, # 3, p. 380 - 391]

88
[ 30169-25-6 ]
[ 6326-27-8 ]
N-(6-(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazin-3-yl)-4-methylbenzimidamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With triethylamine In N,N-dimethyl-formamide at 20℃; for 3h;	General procedure for the synthesis of N-(6-(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazin-3-yl)imidamides 2a-i. General procedure: To 270 mg (1 mmol) of tetrazine 1 in 5 mL of DMF 1 mmol of amidinehydrochloride (in the case of synthesis 2b - benzamidine hydrochloride hydrate, 2d- 4-chlorobenzamidine hydrobromide, 2i - formamidine acetate) and 101 mg (1mmol) Et3N were added. The reaction was stirred for 3 hours at room temperature(2i was stirred while cooling on ice for 1 hour, then kept at room temperature for aday). The reaction mixture was diluted with 10 mL of water, filtered, and washedwith CH2Cl2.

Reference： [1]Charushin, Valery N.; Chupakhin, Oleg N.; Evstigneeva, Natalya P.; Gerasimova, Natalya A.; Ishmetova, Rashida I.; Korotina, Anna V.; Kungurov, Nikolay V.; Rusinov, Gennady L.; Tolshchina, Svetlana G.; Zilberberg, Natalya V. [Beilstein Journal of Organic Chemistry, 2022, vol. 18, p. 243 - 250]

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
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P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
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P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
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P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
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P407	Maintain air gap between stacks/pallets.
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P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 6326-27-8 ] {[proInfo.proName]}

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[ 6326-27-8 ] Synthesis Path-Upstream 1~6

[ 6326-27-8 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 6326-27-8 ]

Aryls

Amidines

Amines

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[ 6326-27-8 ]