[ CAS No. 767-15-7 ] {[proInfo.proName]}

Name: 767-15-7|2-Amino-4,6-dimethylpyrimidine|97%
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SKU: A212791
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Product Details of [ 767-15-7 ]

CAS No. :	767-15-7	MDL No. :	MFCD00006102
Formula :	C₆H₉N₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IDQNBVFPZMCDDN-UHFFFAOYSA-N
M.W :	123.16	Pubchem ID :	13021
Synonyms :

Calculated chemistry of [ 767-15-7 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	36.37
TPSA :	51.8 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) :	-6.58 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.44
Log Po/w (XLOGP3) :	0.67
Log Po/w (WLOGP) :	0.68
Log Po/w (MLOGP) :	0.06
Log Po/w (SILICOS-IT) :	1.06
Consensus Log Po/w :	0.78

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.52
Solubility :	3.73 mg/ml ; 0.0303 mol/l
Class :	Very soluble
Log S (Ali) :	-1.33
Solubility :	5.7 mg/ml ; 0.0463 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.02
Solubility :	1.17 mg/ml ; 0.00951 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.42

Safety of [ 767-15-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 767-15-7 ]

* 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 [ 767-15-7 ]
Downstream synthetic route of [ 767-15-7 ]

[ 767-15-7 ] Synthesis Path-Upstream 1~4

1
[ 767-15-7 ]
[ 4472-44-0 ]

Reference： [1] Journal of Heterocyclic Chemistry, 2004, vol. 41, # 3, p. 343 - 348
[2] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 9, p. 5515 - 5522
[3] Chinese Journal of Chemistry, 2015, vol. 33, # 10, p. 1124 - 1134
[4] Phosphorus, Sulfur and Silicon and the Related Elements, 2016, vol. 191, # 1, p. 48 - 54
[5] Phosphorus, Sulfur and Silicon and the Related Elements, 2017, vol. 192, # 1, p. 34 - 41
[6] Letters in Drug Design and Discovery, 2016, vol. 13, # 4, p. 343 - 351
[7] European Journal of Medicinal Chemistry, 2016, vol. 117, p. 167 - 178
[8] Journal of Fluorine Chemistry, 2016, vol. 184, p. 36 - 44

2
[ 767-15-7 ]
[ 4214-57-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With N-Bromosuccinimide In acetonitrile at 20℃; for 3 h; Inert atmosphere	2-Amino-5-bromo-4,6-dimethylpyrimidine (3):; To a stirred solution containing 4.3 lg (34.75 mmol) of 2-amino-4,6-dimethylpyrimidine (2) in 150 mL of acetonitrile were added 6.15g (52.12 mmol) of N-bromosuccinimide. The reaction mixture was stirred at room temperature under argon atmosphere for 3 h. The formed precipitate was filtered and dried to afford the expected product as a white solid: yield 5.93g (83percent).1H-NMR(CDC1₃) δ 5.19 (br, 2H), 2.44 (s, 6H);¹³C-NMR (CDC1₃) δ 166.28, 160.73, 109.60, 24.70.
83%	With N-Bromosuccinimide In acetonitrile at 23℃; for 3 h; Inert atmosphere	To a stirred solution containing 4.31 g (34.8 mmol) of 2-amino-4,6-dimethylpyrimidine (4) in 150 mL of acetonitrile was added 6.15 g (52.1 mmol) of N-bromosuccinimide. The reaction mixture was stirred at 23 °C for 3 h. The formed precipitate was filtered and dried to afford 5 as a colorless solid: yield 5.93 g (83percent); mp 183-185 °C; silica gel TLC R_f 0.15 (2:1 ethyl acetate/hexanes); ¹H NMR (CDCl₃) δ 2.44 (s, 6H) and 5.19 (br s, 2H); ¹³C NMR (CDCl₃) δ 24.7, 109.6, 160.7 and 166.3; mass spectrum (APCI), m/z 201.9982 (M+H)⁺ (C₆H₉N₃Br requires 201.9980).

Reference： [1] Patent: WO2011/103536, 2011, A1, . Location in patent: Page/Page column 35-37
[2] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 8, p. 608 - 613
[3] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 4, p. 969 - 978
[4] Synthetic Communications, 1991, vol. 21, # 7, p. 901 - 906
[5] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 20, p. 5139 - 5143
[6] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 11, p. 3980 - 3986
[7] Chemische Berichte, 1938, vol. 71, p. 87,99
[8] Biochemical Journal, 1951, vol. 48, p. 394,395

3
[ 767-15-7 ]
[ 57-68-1 ]

Reference： [1] Patent: CH231195, 1938, ,
[2] Journal of Organic Chemistry, 1945, vol. 10, p. 327,329
[3] Journal of the American Chemical Society, 1941, vol. 63, p. 2188
[4] Patent: CH230865, 1938, ,

4
[ 767-15-7 ]
[ 98-74-8 ]
[ 57-68-1 ]

Reference： [1] Patent: US2430439, 1940, ,

[ 767-15-7 ] Synthesis Path-Downstream 1~88

1
[ 590-92-1 ]
[ 767-15-7 ]
6,8-dimethyl-3,4-dihydro-pyrimido[1,2-<i>a</i>]pyrimidin-2-one; hydrobromide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 117,119

2
[ 767-15-7 ]
[ 4214-57-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With N-Bromosuccinimide; In acetonitrile; at 20℃; for 3h;Inert atmosphere;	2-Amino-5-bromo-4,6-dimethylpyrimidine (3):; To a stirred solution containing 4.3 lg (34.75 mmol) of 2-amino-4,6-dimethylpyrimidine (2) in 150 mL of acetonitrile were added 6.15g (52.12 mmol) of N-bromosuccinimide. The reaction mixture was stirred at room temperature under argon atmosphere for 3 h. The formed precipitate was filtered and dried to afford the expected product as a white solid: yield 5.93g (83%).1H-NMR(CDC13) delta 5.19 (br, 2H), 2.44 (s, 6H);13C-NMR (CDC13) delta 166.28, 160.73, 109.60, 24.70.
83%	With N-Bromosuccinimide; In acetonitrile; at 23℃; for 3h;Inert atmosphere;	To a stirred solution containing 4.31 g (34.8 mmol) of 2-amino-4,6-dimethylpyrimidine (4) in 150 mL of acetonitrile was added 6.15 g (52.1 mmol) of N-bromosuccinimide. The reaction mixture was stirred at 23 C for 3 h. The formed precipitate was filtered and dried to afford 5 as a colorless solid: yield 5.93 g (83%); mp 183-185 C; silica gel TLC Rf 0.15 (2:1 ethyl acetate/hexanes); 1H NMR (CDCl3) delta 2.44 (s, 6H) and 5.19 (br s, 2H); 13C NMR (CDCl3) delta 24.7, 109.6, 160.7 and 166.3; mass spectrum (APCI), m/z 201.9982 (M+H)+ (C6H9N3Br requires 201.9980).
	With N-Bromosuccinimide; In acetonitrile; at 80℃; for 6h;	3. The 150 g compound 5, 200g of N - bromosuccinimide added 1 L in acetonitrile, 80 C heated 6 h. Precipitate is filtered, washed with cold acetonitrile, under the condition of vacuum drying, to obtain white solid (compound 6).

Reference： [1]Patent: WO2011/103536,2011,A1 .Location in patent: Page/Page column 35-37
[2]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 608 - 613
[3]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 969 - 978
[4]Synthetic Communications,1991,vol. 21,p. 901 - 906
[5]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5139 - 5143
[6]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 3980 - 3986
[7]Chemische Berichte,1938,vol. 71,p. 87,99
[8]Patent: CN109824604,2019,A .Location in patent: Paragraph 0071; 0074

3
[ 767-15-7 ]
[ 6971-09-1 ]
N-(4,6-dimethylpyrimidin-2-yl)-3-oxo-1,2-benzisothiazole-2(3H)-carboxamide 1,1-dioxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	In toluene Heating;

Reference： [1]Benicha, Mohamed; Azmani, Amina; Akssira, Mohamed; Hurst, Derek T. [Australian Journal of Chemistry, 1993, vol. 46, # 6, p. 903 - 906]

4
[ 767-15-7 ]
[ 16182-04-0 ]
[ 64572-89-0 ]

Yield	Reaction Conditions	Operation in experiment
86.7%	at 40℃; for 6h;	General procedure: The compound 2a(124.1 g, 0.8 mol) was added to the above mentioned solution of 1, and then the mixture was stirred at 40C for 6 h. The obtained mixture was cooled and filtered to achieve the solid which was then washed by50 mL EtOAc. The compound 3a was obtained as the yellow powder, yield 192.4 g (84.0percent);

Reference： [1]Heterocycles,2016,vol. 92,p. 829 - 843
[2]Australian Journal of Chemistry,1988,vol. 41,p. 1221 - 1229

5
[ 767-15-7 ]
[ 532-55-8 ]
[ 121087-84-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	In acetone for 0.5h; Heating;

Reference： [1]Hurst, Derek T.; Stacey, Anthony D.; Nethercleft, Mark; Rahim, Amjad; Harnden, Michael R. [Australian Journal of Chemistry, 1988, vol. 41, # 8, p. 1221 - 1229]

6
[ 767-15-7 ]
[ 463-71-8 ]
[ 92110-86-6 ]

Reference： [1]Journal of the American Chemical Society,1996,vol. 118,p. 6355 - 6369

7
[ 767-15-7 ]
[ 816-39-7 ]
2-(bromomethyl)-2-hydroxy-5,7-dimethyl-1H,2H,3H-imidazo[1,2-a]pyrimidinium bromide [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,2002,vol. 38,p. 590 - 597

8
[ 767-15-7 ]
[ 121-86-8 ]
[ 201230-82-2 ]
1-(3-chloro-4-methyl-phenyl)-3-(4,6-dimethyl-pyrimidin-2-yl)-urea [ No CAS ]

Reference： [1]Journal of Chemical Research - Part S,2003,p. 442 - 444

9
[ 767-15-7 ]
[ 201230-82-2 ]
[ 620-88-2 ]
1-(4,6-dimethyl-pyrimidin-2-yl)-3-(4-phenoxy-phenyl)-urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With selenium; triethylamine In toluene at 150℃; for 4h;

Reference： [1]Ling, Gang; Chen, Jingzhu; Lu, Shiwei [Journal of Chemical Research - Part S, 2003, # 7, p. 442 - 444]

10
[ 767-15-7 ]
[ 5446-92-4 ]
[ 201230-82-2 ]
N-(4,6-dimethyl-2-pyrimidyl)-N'-(6-methoxy-3-pyridyl)urea [ No CAS ]

Reference： [1]Tetrahedron,2003,vol. 59,p. 8251 - 8256

11
[ 767-15-7 ]
[ 4472-44-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; copper dichloride; sodium nitrite; In dichloromethane;	General procedure: 2-Chloro-4,6-disubstituted-pyrimidines 17 were prepared bythe reaction of the diazoniumsalts of 4,6-disubstituted-pyrimidin-2-amines (16) with concentrated hydrochloric acid and ZnCl2 [35].Compound 18 was prepared according to literature [32], and themethod was improved. To a stirred solution of piperazine(45 mmol) and K2CO3 (16.5 mmol) in water (20 mL) was addedchloropyrimidine 17 (18 mmol) in small portions at 50e65 C. Themixture was stirred for 1 h at 60e65 C and cooled to 35 C. Theyellowsolid, 1,4-bispyrimidylpiperazine byproduct, was filtered off,and the filtrate was then extracted three times with chloroform,dried over Na2SO4, and evaporated in vacuum to give compound 18,which was used for the following reactions without further purification.

Reference： [1]Journal of Heterocyclic Chemistry,2004,vol. 41,p. 343 - 348
[2]Journal of Agricultural and Food Chemistry,2010,vol. 58,p. 5515 - 5522
[3]Chinese Journal of Chemistry,2015,vol. 33,p. 1124 - 1134
[4]Phosphorus, Sulfur and Silicon and the Related Elements,2016,vol. 191,p. 48 - 54
[5]Letters in drug design and discovery,2016,vol. 13,p. 343 - 351
[6]European Journal of Medicinal Chemistry,2016,vol. 117,p. 167 - 178
[7]Journal of Fluorine Chemistry,2016,vol. 184,p. 36 - 44

12
[ 767-15-7 ]
[ 1147550-11-5 ]
[ 98-88-4 ]
[ 121087-84-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: ammonium thiocyanate; benzoyl chloride In acetone for 0.0833333h; Heating; Stage #2: 2-Amino-4,6-dimethylpyrimidine In acetone for 0.5h; Heating; Further stages.;

Reference： [1]Dovlatyan; Eliazyan; Ghazaryan; Yengoyan [Chemistry of Heterocyclic Compounds, 2006, vol. 42, # 3, p. 389 - 391]

13
[ 767-15-7 ]
[ 333-20-0 ]
[ 88067-09-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride In acetonitrile

Reference： [1]Sun, Chuanwen; Zhang, Xiaodong; Huang, Hai; Zhou, Pei [Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 24, p. 8574 - 8581]

14
[ 50-01-1 ]
[ 123-54-6 ]
[ 767-15-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In water; at 40℃; for 24h;	2. The 200 g of 2, 4 - pentanedionato (compound 3), 200 g of the GuHCl (compound 4) is dissolved in 2 L of water, gradually adding 550 g potassium carbonate. The reaction mixture in the 40 °C under stirring 24 h. Precipitate is filtered, washed with water, repeated 3 times. Drying under vacuum, to obtain pale white solid (compound 5).

Reference： [1]Australian Journal of Chemistry,2007,vol. 60,p. 120 - 123
[2]European Journal of Organic Chemistry,2018,vol. 2018,p. 5921 - 5934
[3]Synthetic Communications,2020,vol. 50,p. 649 - 658
[4]Patent: CN109824604,2019,A .Location in patent: Paragraph 0071; 0073

15
[ 767-15-7 ]
[ 696-62-8 ]
(4,6-dimethyl-pyrimidin-2-yl)-bis-(4-methoxy-phenyl)-amine [ No CAS ]

Reference： [1]Chemical Communications,2007,p. 3186 - 3188

16
[ 767-15-7 ]
[ 1829-28-3 ]
(4,6-dimethyl-pyrimidin-2-yl)-bis-(2-carboethoxy-phenyl)-amine [ No CAS ]

Reference： [1]Chemical Communications,2007,p. 3186 - 3188

17
[ 767-15-7 ]
[ 591-50-4 ]
(4,6-dimethyl-pyrimidin-2-yl)-diphenyl-amine [ No CAS ]

Reference： [1]RSC Advances,2015,vol. 5,p. 28879 - 28884
[2]Chemical Communications,2007,p. 3186 - 3188

18
[ 767-15-7 ]
[ 88067-09-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: acetone / 0.08 h / Heating 1.2: 87 percent / acetone / 0.5 h / Heating 2.1: 95 percent / NaOH / 0.5 h / Heating
	Multi-step reaction with 2 steps 1: 82 percent / acetone / 24 h / Heating 2: 90 percent / 2M aq. NaOH / Ambient temperature
	Multi-step reaction with 2 steps 1: 95 percent / acetone / 0.5 h / Heating 2: 94 percent / 2M aq. NaOH / Ambient temperature

Reference： [1]Dovlatyan; Eliazyan; Ghazaryan; Yengoyan [Chemistry of Heterocyclic Compounds, 2006, vol. 42, # 3, p. 389 - 391]
[2]Hurst, Derek T.; Stacey, Anthony D.; Nethercleft, Mark; Rahim, Amjad; Harnden, Michael R. [Australian Journal of Chemistry, 1988, vol. 41, # 8, p. 1221 - 1229]
[3]Hurst, Derek T.; Stacey, Anthony D.; Nethercleft, Mark; Rahim, Amjad; Harnden, Michael R. [Australian Journal of Chemistry, 1988, vol. 41, # 8, p. 1221 - 1229]

19
[ 767-15-7 ]
[ 85953-41-9 ]
[ 111-36-4 ]
N-[(4.6-dimethylpyrimidin-2-yl)aminocarbonyl]-1H-indole-2-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide;1,4-diaza-bicyclo[2.2.2]octane; In acetonitrile;	EXAMPLE 6 Preparation of N-[(4.6-dimethylpyrimidin-2-yl)aminocarbonyl]-<strong>[85953-41-9]1H-<strong>[85953-41-9]indole-2-sulfonamide</strong></strong> A mixture of 5.0 g (0.0255 mole) of <strong>[85953-41-9]1H-<strong>[85953-41-9]indole-2-sulfonamide</strong></strong>, 2.9 ml (0.0255 mole) of n-butylisocyanate, a catalytic amount of 1,4-diazabicyclo[2,2,2] octane and 75 ml of xylenes was heated under nitrogen to 138. Phosgene was condensed into the reaction mixture until the temperature fell to 130. As phosgene was consumed, the temperature gradually increased to 138. Further additions of phosgene were made until the reaction temperature failed to return to 138. Unreacted phosgene was removed with a nitrogen stream (2N NaOH trap) and heating was continued for 15 minutes. The reaction mixture was cooled to room temperature, filtered under nitrogen and evaporated in vacuo to afford the sulfonylisocyanate intermediate which was used without purification in the second step of the reaction. A solution of 1.0 g (4.47 mmol) of the above isocyanate in 5 ml dry acetonitrile was added under nitrogen to a mixture of 0.5 g (4.06 mmol) of 2-amino-4.6-dimethylpyrimidine in 5 ml dry acetonitrile and the mixture allowed to stir overnight at ambient temperature. The precipitate was collected by filtration and washed with ether to afford the desired material.

Reference： [1]Patent: US4764610,1988,A

20
[ 767-15-7 ]
[ 43036-06-2 ]
[ 1189-71-5 ]
[ 7732-18-5 ]
1-(2-cyanoethyl)-N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-1H-pyrrole-2-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	aluminum (III) chloride; In tetrahydrofuran;	EXAMPLE 3 Preparation of 1-(2-cyanoethyl)-N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-1H-pyrrole-2-sulfonamide. To a stirred suspension of 2.59 g (0.021 mole) of 2-amino-4,6-dimethylpyrimidine in 80 ml dry tetrahydrofuran at -70 C. under nitrogen was added dropwise via syringe 2.0 ml (0.023 mole) of chlorosulfonyl isocyanate at such a rate to maintain the temperature of the reaction mixture below -55 C. The resulting solution was stirred 0.5 hour at -70, then treated dropwise with a solution of 2.4 ml (0.021 mol) of N-(2-cyanoethyl)pyrole in 10 ml dry THF. A catalytic amount (approximately 0.2 to 0.3 gm) of aluminum (III) chloride was added and the reaction mixture allowed to warm to ambient temperatures and stirred for an additional 18 hours. The reaction mixture was poured into 300 ml of H2 O and extracted with three portions of dichloromethane. The organic solutions were washed with water, dried over MgSO4 and evaporated. Trituration with a small volume of CH2 Cl2 afforded 1.2 g of the desired product as a white microcrystalline solid, m.p. 158-159 C. The infrared spectrum of the product included absorptions at 3250 and 3110 (NH), 2240 (C N), 1685 (C=O), 1350 and 1160 cm-1 (SO2).

Reference： [1]Patent: US4368067,1983,A

21
[ 767-15-7 ]
[ 26638-43-7 ]
[ 74222-97-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	In acetonitrile;	EXAMPLE 1 Preparation of 2-[[(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester A slurry of 7.0 grams (0.057 moles) of 4,6-dimethyl-2-pyrimidinamine, 6.0 grams (0.092 moles) sodium cyanate, and 13.5 grams (0.057 moles) 2-carbomethoxybenzenesulfonyl chloride in 60 ml acetonitrile was stirred 1 hour at reflux (81). The reaction was diluted with 60 ml water, allowed to cool to room temperature and filtered. The solid was washed with 20 ml water and dried. There was obtained 16.0 grams (77.0% of theory) of the title compound. The product was 98% pure as assayed by high pressure liquid chromatography. The m.p. and IR spectrum of the title compound were identical to those of an authentic sample prepared as described in U.S. Pat. No. 4,394,506.

Reference： [1]Patent: US4546179,1985,A

22
[ 767-15-7 ]
[ 10294-28-7 ]
[ 134040-68-9 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1991,vol. 64,p. 744 - 746

23
[ 767-15-7 ]
[ 10294-28-7 ]
2Au⁽³⁺⁾*4C₄N₂H(CH₃)2NH₂*6Br^(1-)={Au(C₄N₂H(CH₃)2NH₂)2Br}2Br₄ [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1991,vol. 64,p. 744 - 746

24
[ 767-15-7 ]
[ 870837-41-5 ]
[ 1185015-76-2 ]

Yield	Reaction Conditions	Operation in experiment
62%	With sodium phenoxide;tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 80℃; for 2h;Inert atmosphere;	b) 5-(4,6-Dimethyl-pyrimidin-2-ylamino)-2-(4-methyl-imidazol-1-yl)-benzonitrile; A mixture of 5-bromo-2-(4-methyl-imidazol-1-yl)-benzonitrile (200 mg, 0.76 mmol), 2-amino-4,6-dimethyl-pyrimidine (141 mg, 1.14 mmol), sodium phenoxide (266 mg, 2.29 mmol), tris(dibenzylideneacetone)dipalladium chloroform complex (21 mg, 0.02 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene=xanthphos (26 mg, 0.04 mmol) in 5 mL of dioxane was heated to 80° C. under argon for 2 hours. The mixture was diluted with water, extracted with ethyl acetate and the product purified by chromatography on silica gel using dichloromethane/methanol 9:1 v/v as an eluent. The title compound was obtained as a colorless solid (144 mg, 62percent). MS ISP (m/e): 305.1 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): delta (ppm)=10.08 (s, 1H), 8.44 (s, 1H), 8.15 (d, 1H), 7.89 (s, 1H), 7.55 (d, 1H), 7.25 (s, 1H), 6.76 (s, 1H), 2.36 (s, 6H), 2.18 (s, 3H).

Reference： [1]Patent: US2009/215759,2009,A1 .Location in patent: Page/Page column 55

25
[ 767-15-7 ]
[ 36016-40-7 ]
[ 446839-32-3 ]

Yield	Reaction Conditions	Operation in experiment
62%	In dichloromethane; at 0℃;	To a solution of 4,6-Dimethyl-pyrimidin-2-ylamine (25 g, 200 mmol) in 400 mL of CH2Cl2 was added dropwise a solution of hydroxylamine-2,4,6-Trimethyl-benzenesulfonate (105 g, 488 mmol) in 300 mL of CH2Cl2 at 0° C., and the mixture was stirred at 0° C. for 1 hand filtered. The solid collected was washed with CH2Cl2 (100 mL) to give 1-Amino-4,6-dimethyl-1H-pyrimidin-2-ylidene-ammonium 2,4,6-Trimethyl-benzenesulfonate (40 g, yield: 62percent).
62%	In dichloromethane; at 0℃; for 1h;	Example 52-Chloromethyl-5,7-dimethyl-[1,2,4]triazolo[1 ,5-a]pyrimidine1-Amino-4,6-dimethyl-1 H-pyrimidin-2-ylidene-ammonium 2,4,6-Trimethyl-benzenesulfonate2-Chloromethyl-5,7-dimethyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidineTo a solution of 4,6-Dimethyl-pyrimidin-2-ylamine (25 g, 200 mmol) in 400 ml_ of CH2CI2 was added dropwise a solution of hydroxylamine-2,4,6-Trimethyl- benzenesulfonate (105 g, 488 mmol) in 300 ml_ of CH2CI2 at 0°C, and the mixture was stirred at 0°C for 1 hour and filtered. The solid collected was washed with CH2CI2 (100 ml_) to give 1 -Amino-4,6-dinnethyl-1 H-pyrimidin-2- ylidene-amnnoniunn 2,4,6-trinnethyl-benzenesulfonate (40 g, yield:62percent).
62%	In dichloromethane; at 0℃; for 1h;	Preparation of other intermediates2-Chloromethyl-5,7-dimethyl-[1,2,4]triazolo[1 ,5-a]pyrimidine 2-Chloromethyl-5,7-dimethyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidineTo a solution of 4,6-Dimethyl-pyhmidin-2-ylannine (25 g, 200 mmol) in 400 mL of CH2CI2 was added dropwise a solution of hydroxylamine-2,4,6-Trimethyl- benzenesulfonate (105 g, 488 mmol) in 300 mL of CH2CI2 at 0°C, and the mixture was stirred at 0°C for 1 hour and filtered. The solid collected was washed with CH2CI2 (100 mL) to give 1 -Amino-4,6-dimethyl-1 H-pyrimidin-2- ylidene-ammonium 2,4,6-Trimethyl-benzenesulfonate (40 g, yield:62percent).

62%	In dichloromethane; at 0℃; for 1h;	To a solution of 4,6-Dimethyl-pyhmidin-2-ylamine (25 g, 200 mmol) in 400 ml_ of CH2CI2 was added dropwise a solution of hydroxylamine-2,4,6-Trimethyl- benzenesulfonate (105 g, 488 mmol) in 300 ml_ of CH2CI2 at 0°C, and the mixture was stirred at 0°C for 1 hour and filtered. The solid collected was washed with CH2CI2 (100 ml_) to give 1 -Amino-4,6-dimethyl-1 H-pyrimidin-2-ylidene-ammonium 2,4,6-Trimethyl-benzenesulfonate (40 g, yield:62percent).
62%	In dichloromethane; at 0℃;	4,6-Dimethyl-pyrimidin-2-ylamine 1-Amino-4,6-dimethyl-1 H-pyrimidin-2 -ylidene-ammonium 2,4,6-Trimethyl-benzenesulfonate 2-Chloromethyl-5,7-dimethyl-[1 ,2,4] triazolo[1 ,5-a]pyrimidineTo a solution of 4,6-Dimethyl-pyrimidin-2-ylamine (25 g, 200 mmol) in 400 ml_ of CH2CI2 was added dropwise a solution of hydroxylamine-2,4,6-Trimethyl- benzenesulfonate (105 g, 488 mmol) in 300 ml_ Of CH2CI2 at O0C, and the mixture was stirred at OoC for 1 hand filtered. The solid collected was washed with CH2CI2 (100 ml_) to give 1-Amino-4,6-dimethyl-1 H-pyrimidin-2-ylidene-ammonium 2,4,6-Trimethyl- benzenesulfonate (40 g, yield:62percent).
	In dichloromethane; at 20℃; for 3h;	a.1-Amino-4,6-dimethylpyridin-2(1H)-iminium-2,4,6-trimethyl-benzenesulfonateA solution of O-(mesitylsulfonyl)hydroxylamine (1.65 g, 7.65 mmol) in DCM (20 mL) was stirred at room temperature, and 4,6-dimethylpyrimidine (0.313 g, 2.55 mmol) was added slowly.The reaction mixture was stirred at room temperature for 3 h, then the solvent was removed under reduced pressure, and the crude product was used for the next step without further purification. ESI MS: m/z 139 [M+H]+.

Reference： [1]Patent: US2010/16303,2010,A1 .Location in patent: Page/Page column 20
[2]Patent: WO2011/72696,2011,A1 .Location in patent: Page/Page column 40-41
[3]Patent: WO2011/72697,2011,A1 .Location in patent: Page/Page column 41-43
[4]Patent: WO2011/72694,2011,A1 .Location in patent: Page/Page column 45-46
[5]Patent: WO2009/152825,2009,A1 .Location in patent: Page/Page column 48
[6]Patent: US2012/178748,2012,A1 .Location in patent: Page/Page column 40

26
[ 767-15-7 ]
[ 534-07-6 ]
2-chloromethyl-5,7-dimethyl-imidazo[1,2-a]pyrimidine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%		A solution of <strong>[767-15-7]2-amino-4,6-dimethylpyrimidine</strong> (2.46 g, 20.0 mmol) and 1,3-dichloro-2-propanone (2.67 g, 21.0 mmol) in 1,2-dimethoxyethane (20 mL) was stirred at 45° C. overnight. A precipitate formed, and this was collected by filtration, and was then refluxed with ethanol (15 mL) for 2 hours. After cooling to room temperature, the product precipitated as white needles which were collected by filtration and vacuum dried to yield the title compound pure as its hydrochloride salt (883 mg, 19percent). 1H NMR (500 MHz, DMSO-d6): delta7.84 (s, 1H), 6.88 (s, 1H), 4.84 (s, 2H), 2.60 (s, 3H), 2.49 (s, 3H).
19%		2-Chloromethyl-5,7-dimethyl-imidazo[1 ,2-a]pyrimidine A solution of 2-amino-4,6-dimethylpyhnnidine (2.46 g, 20.0 mmol) and 1 ,3-dichloro- 2-propanone (2.67 g, 21 .0 mmol) in 1 ,2-dimethoxyethane (20 mL) was stirred at 45 °C overnight. A precipitate formed, and this was collected by filtration, and was then refluxed with ethanol (15 mL) for 2 hours. After cooling to room temperature, the product precipitated as white needles which were collected by filtration and vacuum dried to yield the title compound pure as its hydrochloride salt (883 mg, 19percent). 1H NMR (500 MHz, DMSO-c/6): delta 7.84 (s, 1 H), 6.88 (s, 1 H), 4.84 (s, 2H), 2.60 (s, 3H), 2.49 (s, 3H).
19%		2-Chloromethyl-5,7-dimethyl-imidazo[1,2-a]pyrimidine A solution of <strong>[767-15-7]2-amino-4,6-dimethylpyrimidine</strong> (2.46 g, 20.0 mmol) and 1 ,3-dichloro-2- propanone (2.67 g, 21.0 mmol) in 1 ,2-dimethoxyethane (20 ml_) was stirred at 45 0C overnight. A precipitate formed, and this was collected by filtration, and was then refluxed with ethanol (15 ml_) for 2 hours. After cooling to room temperature, the product precipitated as white needles which were collected by filtration and vacuum dried to yield the title compound pure as its hydrochloride salt (883 mg, 19percent). 1H NMR (500 MHz, DMSO-de): delta7.84 (s, 1 H), 6.88 (s, 1 H), 4.84 (s, 2H), 2.60 (s, 3H), 2.49 (s, 3H).

Reference： [1]Patent: US2010/16303,2010,A1 .Location in patent: Page/Page column 20
[2]Patent: WO2011/72694,2011,A1 .Location in patent: Page/Page column 44-45
[3]Patent: WO2009/152825,2009,A1 .Location in patent: Page/Page column 47

27
[ 767-15-7 ]
[ 534-07-6 ]
[ 690642-33-2 ]

Yield	Reaction Conditions	Operation in experiment
63%	In Dimethyl ether; at 45℃; for 10h;	1,3-dichloroacetone (5.6 g, 41.0 mmol) and intermediatea2 (5.0 g, 41.0 mmol) were solubilized in dimethyl ether(30 mL), the mixture was stirred at 45 C for 10 h . The resulting precipitate was filtered, added to ethanol (50 mL) and the mixturewas refluxed for 2 h. The solvent was removed under reduced pressure,water (30 mL) was added and the mixture was adjusted to pH8-9 with saturated sodium carbonate solution. The resulting precipitatewas filtered, washed with water and dried under reducedpressure to yield the title compound as a white solid (5.1 g, 63%).MS [M+H]+ m/z: 196.
63%	In Dimethyl ether; at 45℃; for 10h;	Dissolve 5.63 g (0.041 mol) of 1,3-dichloropropan-2-one in 30 mL of dimethyl ether, add 5 g (0.041 mol) of intermediate a2, and raise the temperature to 45 C for reaction. A white solid is produced during the reaction. After 10 hours of reaction, suction filtration was performed. The filter cake was added to absolute ethanol for 2 hours to complete the reaction. Evaporate the ethanol, add water and stir for 30 min, suction filter, wash the filter cake with water, and dry to obtain 5.03 g of white solid with a yield of 63%.

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 2621 - 2631
[2]Patent: CN110229150,2019,A .Location in patent: Paragraph 0135; 0138; 0141; 0142

28
[ 767-15-7 ]
[ 1969-44-4 ]
[ 886173-90-6 ]

Yield	Reaction Conditions	Operation in experiment
62%	In N,N-dimethyl-formamide at 120℃;

Reference： [1]Location in patent: body text Guellue, Mustafa; Dincsoenmezl, Ali; Oezyavas, Oeznur [European Journal of Organic Chemistry, 2010, # 11, p. 2113 - 2120]

29
[ 506-93-4 ]
[ 123-54-6 ]
[ 767-15-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium carbonate; In water; at 80℃; for 7h;	A mixtureof guanidine nitrate (3.0 g, 25.0 mmol), 2,4-pentandione(3.7 g, 37.0 mmol), K2CO3 (3.4 g, 25.0 mmol) and distilled water(15 mL) was stirred at 80 C for 7 h. After that, the mixture wascooled to rt and the resulting precipitate was filtered, washed withwater and dried under reduced pressure to yield the title compoundas a white solid (2.6 g, 96%). MS [M+H]+ m/z: 123.
96%	With potassium carbonate; In water; at 80℃; for 7h;	3g (0.025mol) guanidine nitrate,3.7g (0.037mol) of 2,4-pentanedione,3.4 g (0.025 mol) of potassium carbonate and 15 mL of distilled water were added to a 50 mL eggplant-shaped bottle, heated to 80 C., and reacted for 7 hours. The reaction solution was slowly lowered to room temperature, suction filtered, and the filter cake was washed with a small amount of distilled water. The filter cake was dried to obtain 2.59 g of a white solid with a yield of 96%.
69.5%		A solution of guanidine nitrate (122.1 g, 1 mol)and 2,4-pentanedione (120.1 g, 1.2 mol) in water (800 mL) was stirred vigorously for 0.5 h at roomtemperature, and then sodium carbonate (74.2 g, 0.7 mol) was added. The resultant mixture was refluxed for 3 h, after that the mixture was cooled to the room temperature. The compound 2b as the white precipitate was separated from the reaction solution, yield 85.6 g (69.5%); mp 153.8-154.5 C[lit.152-154 C]25; 1H-NMR (400 MHz, CDCl3): delta 6.38 (s, 1H, pyrimidine), 5.24 (s, 2H, NH2), 2.29 (s, 6H,2 × CH3); Anal. Calcd for C6H9N3: C 58.51, H 7.37, N 34.12. Found C 58.74, H 6.98, N 34.28.

52.3 g

With sodium carbonate; In water; at 80℃; for 4h;

To a 500 mL three-necked flask equipped with a stirrer, a thermometer, and a condenser reflux tube,Add 125mL of water, 70g of guanidine nitrate, 45g of sodium carbonate, and 50g of acetylacetone, and turn on the stirring.heating. The temperature was raised slowly to 80 C., and the mixture was stirred. After the reaction was conducted for 4 h, the heating device was removed, and the mixture was stirred at room temperature for 12 h. A large amount of white solids appeared in the three-vial flask. It is suction filtered and washed with water to give a white solid,The product was dried in an oven to give 52.3 g of 2-amino-4,6-dimethylpyrimidine.

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 2621 - 2631
[2]Patent: CN110229150,2019,A .Location in patent: Paragraph 0135; 0138; 0139; 0140
[3]Heterocycles,2016,vol. 92,p. 829 - 843
[4]Polish Journal of Chemistry,2009,vol. 83,p. 1601 - 1607
[5]Patent: CN107663178,2018,A .Location in patent: Paragraph 0008; 0021; 0022

30
[ 767-15-7 ]
[ 4534-68-3 ]
[ 7732-18-5 ]
[ 20667-12-3 ]
[Ag₄(2-amino-4,6-dimethylpyrimidine)6(1,2,3,4-butanetetracarboxylate)]*2H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With aq. NH₃ In methanol; water Sonication; in the darkness; mixt. of Ag2O and two ligands stirred in MeOH-H2O; aq. NH3 soln. added dropwise; ultrasonicated; evapd. slowly in the darkness at room temp. for several d; washed with cold EtOH and Et2O; elem. anal.;

Reference： [1]Sun, Di; Zhang, Na; Xu, Qin-Juan; Huang, Rong-Bin; Zheng, Lan-Sun [Journal of Molecular Structure, 2010, vol. 975, # 1-3, p. 17 - 22]

31
[ 767-15-7 ]
[ 13089-11-7 ]
[ 1236112-72-3 ]

Reference： [1]Journal of Fluorine Chemistry,2010,vol. 131,p. 1044 - 1048
[2]Russian Chemical Bulletin,2009,vol. 58,p. 1476 - 1478
[3]Phosphorus, Sulfur and Silicon and the Related Elements,2013,vol. 188,p. 179 - 182

32
[ 67-56-1 ]
[ 767-15-7 ]
C₈H₉N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 1029; Step A; To commercially available 4,6-dimethyl-pyrimidin-2-ylamine (6.0 g) in water (400 mL) was added a solution of sodium hydroxide (1.3 g in 5 mL water) and heated at 80° C. for 10 min. Then potassium permanganate (15 g) was added and heated between 85° C. to 90° C. for 1 h. Potassium permanganate (15 g) was again added and mixture was heated for another 2 h. The mixture was cooled to room temperature and filtered through Celite.(R). and then acidified to pH 2. The mixture was concentrated to 20percent of the original volume and the solid was filtered and dried. To solid was dissolved in methanol (200 mL) and saturated with dry hydrogen chloride gas and the mixture was heated to reflux for 24 h. The mixture was concentrated to an oil and then taken up in dichloromethane and the organic phase was washed with saturated NaHCO3 and then dried over MgSO4, filtered and concentrated to give a solid which was purified by column chromatography (silica, 10percent methanol/dichloromethane) to give the intermediate (0.41 g). [MH]+=212.; Example 1030; Step A; To commercially available 4,6-dimethyl-pyrimidin-2-ylamine (6.0 g) in water (400 mL) was added a solution of sodium hydroxide (1.3 g in 5 mL water) and heated at 80° C. for 10 min. Then potassium permanganate (15 g) was added and heated between 85° C. to 90° C. for 1 h. Potassium permanganate (15 g) was again added and mixture was heated for another 2 h. The mixture was cooled to room temperature and filtered through Celite.(R). and then acidified to pH 2. The mixture was concentrated to 20percent of the original volume and the solid was filtered and dried. To solid was dissolved in methanol (200 mL) and saturated with dry hydrogen chloride gas and the mixture was heated to reflux for 24 h. The mixture was concentrated to an oil and then taken up in dichloromethane and the organic phase was washed with saturated NaHCO3 and then dried over MgSO4, filtered and concentrated to give a solid which was purified by column chromatography (silica, 10percent methanol/dichloromethane) to give the intermediate (0.41 g). [MH]+=212.

Reference： [1]Patent: US2007/155739,2007,A1 .Location in patent: Page/Page column 67-68; 69

33
[ 594-14-9 ]
[ 123-54-6 ]
[ 767-15-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium carbonate; In water; at 100℃;Product distribution / selectivity;	2-Amino-4,6-dimethylpyrimidine (2):; To a stirred solution containing 4.00g (36.99 mmol) of guanidine sulfate and 8.40g (79.25 mmol) of sodium carbonate in 25 mL of water were added 6.00 mL (58.12 mmol) of 2,4- pentadienone. The reaction mixture was stirred at 100 °C overnight. The reaction mixture was poured into 150 mL of water and then extracted with two portions of 150 mL of dichloromethane. The combined organic solution was washed with a 150 mL portion of brine, dried (MgSC^) and then concentrated under diminished pressure to afford the expected product as a white solid: yield 4.3 lg (95percent). 1H-NMR(CDC13) delta 6.33 ( s, 1H), 5.39 (br, 2H), 2.24 (s, 6H);13C-NMR (CDC13) delta 167.72, 162.90, 110.45, 23.66.

Reference： [1]Patent: WO2011/103536,2011,A1 .Location in patent: Page/Page column 35-36

34
[ 646-34-4 ]
[ 123-54-6 ]
[ 767-15-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium carbonate; In water; at 100℃; for 24h;Inert atmosphere;	To a stirred solution containing 4.00 g (37.0 mmol) of guanidine sulfate and 8.40 g (79.3 mmol) of sodium carbonate in 25 mL of water was added 6.00 mL (5.88 g; 58.1 mmol) of 2,4-pentanedione. The reaction mixture was stirred at 100 °C for 24 h. The cooled reaction mixture was poured into 150 mL of water and then extracted with two 150-mL portions of dichloromethane. The combined organic phase was washed with 150 mL of brine, dried (MgSO4) and then concentrated under diminished pressure to afford 4 as a colorless solid: yield 4.31 g (95percent); mp 152-153 °C; silica gel TLC Rf 0.50 (9:1 dichloromethane/methanol); 1H NMR (CDCl3) delta 2.24 (s, 6H), 5.39 (br s, 2H) and 6.33 (s, 1H); 13C NMR (CDCl3) delta 23.7, 110.5, 162.9 and 167.7; mass spectrum (APCI), m/z 124.0869 (M+H)+ (C6H10N3 requires 124.0875).

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 608 - 613
[2]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 969 - 978

35
[ 767-15-7 ]
[ 58142-97-5 ]
N-(4,6-dimethylpyrimidin-2-yl)-5-nitroisoquinolin-1-amine [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2013,vol. 61,p. 747 - 756

36
[ 53112-28-0 ]
[ 767-15-7 ]
[ 25513-98-8 ]
[ 1449337-59-0 ]
[ 1449337-60-3 ]
[ 1449337-61-4 ]
[ 1449337-62-5 ]
C₁₂H₁₃N₃O [ No CAS ]
C₁₂H₁₃N₃O [ No CAS ]
[ 62-53-3 ]

Reference： [1]Journal of Mass Spectrometry,2013,vol. 48,p. 983 - 987

37
[ 767-15-7 ]
[ 104-88-1 ]
[ 1456630-24-2 ]

Yield	Reaction Conditions	Operation in experiment
	With guanidine hydrochloride; In neat (no solvent); at 120℃; for 1h;	General procedure: A mixture ofheteroarylamine (2 mmol), aldehyde (1 mmol), and guanidinium chloride(0.1 mmol) was heated at 120 C for 15?70 min (Table 1), in an oil-bathunder solvent-free conditions. Upon completion, as monitored by TLC, themixture was cooled to 80 C, then glyoxal (40percent aqueous solution, 1 mmol) wasadded and the mixture stirred at the same temperature for 5?15 min asindicated in Table 1. After completion, the mixture was cooled to room temperature and EtOH (5 mL) was added until solid products precipitated. Theprecipitate was filtered, washed with EtOH, and dried. The crude product waspurified by column chromatography on silica gel (n-hexane/EtOAc, 30/70) toafford the corresponding pure white products 4.

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 5730 - 5733

38
[ 767-15-7 ]
[ 582-17-2 ]
[ 623-27-8 ]
[ 1447758-44-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	With formic acid; In neat (no solvent); at 80℃; for 0.25h;Green chemistry;	General procedure: A mixture of heteroaryl amine(2.0 mmol), terephthaldehyde (1.0 mmol) and naphthol (2.0mmol) in the presence of formic acid (0.1 mmol) as catalystwas magnetically stirred on a preheated oil bath at 80 ° C forthe appropriate amount of time as indicated in (Table 1). Theprogress of the reaction was monitored by thin-layer chromatography(TLC). After completion, the reaction mixture wascooled to room temperature and EtOH (5 mL) was addeduntil solid products precipitated. The precipitate was filtered,washed with cold ethanol and dried. The crude product wasstirred for 5 min in boiling EtOH and the resulting whiteprecipitate was filtered. The obtained products 7 were foundto be pure upon TLC examination (Ethyl acetate/ n-Hexane:1/2).

Reference： [1]Letters in Organic Chemistry,2013,vol. 10,p. 311 - 316

39
[ 120-72-9 ]
[ 767-15-7 ]
[ 6334-18-5 ]
[ 1555971-54-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	With N,N,N?,N?-tetrabromobenzene-1,3-disulfonamide; at 20℃; for 0.666667h;Green chemistry;	General procedure: To a stirred mixture of 4-methylbenzaldehyde (1 mmol, 0.120 g) and N,N,N',N'-tetrabromobenzene-1,3-disulfonamide [TBBDA] (0.05 g, 0.09 mmol) or poly(N-bromo-N-ethyl-benzene-1,3-disulfonamide) [PBBS] (0.12 g) at room temperature, was added 2-amino-4,6-dimethylpyrimidin (1 mmol, 0.123 g). Then, indole (1 mmol, 0.12 g) was added to the mixture after 10 min. The progress of the reaction was monitored by TLC (n-hexane/acetone, 17:2). After completion of the reaction, EtOH (5 mL) was added to the reaction mixture and the colorless precipitate was filtered (after evaporation of the ethanol, cool methylene dichloride (2 mL) was added, and the catalyst was recovered), washed with EtOH and dried and purified by recrystallization from ethanol.

Reference： [1]Comptes Rendus Chimie,2014,vol. 17,p. 118 - 123

40
[ 120-72-9 ]
[ 767-15-7 ]
[ 100-52-7 ]
[ 1555971-58-8 ]

Yield	Reaction Conditions	Operation in experiment
80%	With N,N,N?,N?-tetrabromobenzene-1,3-disulfonamide; at 20℃; for 0.5h;Green chemistry;	General procedure: To a stirred mixture of 4-methylbenzaldehyde (1 mmol, 0.120 g) and N,N,N',N'-tetrabromobenzene-1,3-disulfonamide [TBBDA] (0.05 g, 0.09 mmol) or poly(N-bromo-N-ethyl-benzene-1,3-disulfonamide) [PBBS] (0.12 g) at room temperature, was added 2-amino-4,6-dimethylpyrimidin (1 mmol, 0.123 g). Then, indole (1 mmol, 0.12 g) was added to the mixture after 10 min. The progress of the reaction was monitored by TLC (n-hexane/acetone, 17:2). After completion of the reaction, EtOH (5 mL) was added to the reaction mixture and the colorless precipitate was filtered (after evaporation of the ethanol, cool methylene dichloride (2 mL) was added, and the catalyst was recovered), washed with EtOH and dried and purified by recrystallization from ethanol.

Reference： [1]Comptes Rendus Chimie,2014,vol. 17,p. 118 - 123

41
[ 120-72-9 ]
[ 767-15-7 ]
[ 104-87-0 ]
[ 1555971-51-1 ]

Yield	Reaction Conditions	Operation in experiment
93%	With N,N,N?,N?-tetrabromobenzene-1,3-disulfonamide; at 20℃; for 0.416667h;Green chemistry;	General procedure: To a stirred mixture of 4-methylbenzaldehyde (1 mmol, 0.120 g) and N,N,N',N'-tetrabromobenzene-1,3-disulfonamide [TBBDA] (0.05 g, 0.09 mmol) or poly(N-bromo-N-ethyl-benzene-1,3-disulfonamide) [PBBS] (0.12 g) at room temperature, was added 2-amino-4,6-dimethylpyrimidin (1 mmol, 0.123 g). Then, indole (1 mmol, 0.12 g) was added to the mixture after 10 min. The progress of the reaction was monitored by TLC (n-hexane/acetone, 17:2). After completion of the reaction, EtOH (5 mL) was added to the reaction mixture and the colorless precipitate was filtered (after evaporation of the ethanol, cool methylene dichloride (2 mL) was added, and the catalyst was recovered), washed with EtOH and dried and purified by recrystallization from ethanol.

Reference： [1]Comptes Rendus Chimie,2014,vol. 17,p. 118 - 123

42
[ 767-15-7 ]
[ 679406-03-2 ]
[ 1602681-86-6 ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile; at 150℃; for 3.0h;Microwave irradiation;	Step 1 Ethyl 6-chloro-4-(4,6-dimethylpyrimidin-2-ylamino)pyridazine-3-carboxylate A microwave vessel was charged with 4,6-dimethylpyrimidin-2-amine (682 mg, 5.54 mmol), <strong>[679406-03-2]ethyl 4,6-dichloropyridazine-3-carboxylate</strong> (0.306 g, 1.38 mmol) and acetonitrile (0.50 mL). The mixture was and heated under microwave irradiation at 150 C for 3 h. After cooling, the mixture was adsorbed on silica gel and purified by chromatography (silica gel 45 muMu, 80 g, Thomson, eluting with 0 to 10 % of a 9: 1 MeOH:NH4OH solution in CH2C12, 20 min) to give ethyl 6-chloro-4-(4,6-dimethylpyrimidin-2-ylamino)pyridazine-3-carboxylate (85 mg) as a brown foam which was ~60 % pure and used directly in the next reaction without further purification.

Reference： [1]Patent: WO2014/60371,2014,A1 .Location in patent: Page/Page column 79

43
[ 767-15-7 ]
[ 959935-47-8 ]
3,3',5,5'-tetrakis[(4,6-dimethylpyrimidin-2-yl)aminomethyl]-2,2',4,4',6,6'-hexamethyldiphenylmethane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%		To a suspension of NaOH (192 mg, 4.80 mmol) in DMF (10 mL) 2-amino-4,6-dimethyl-pyrimidine (24) (592 mg, 4.80 mmol) was added and stirred at room temperature for 30 min. Then compound 20 (500 mg, 0.80 mmol) was added and the reaction mixture stirred for 72 h at 80 °C. Afterwards, the mixture was poured into ice water (100 mL), the formed precipitate filtered off, washed thoroughly with distilled water. The crude product was purified by column chromatography (aluminium oxide, CHCl3/Et2O 3:1, Rf=0.69). The desired product was obtained as a white solid (330 mg, 52percent), mp 139 °C. 1H NMR (400 MHz, CDCl3): delta 6.31 (s, 4H), 4.89 (t, J=4.3 Hz, 4H), 4.55 (d, J=4.4 Hz, 8H), 4.14 (s, 2H), 2.28 (s, 24H), 2.12 (s, 12H) ppm. 13C NMR (100 MHz, CDCl3): delta=167.33, 161.86, 137.29, 135.82, 134.59, 133.30, 109.59, 41.19, 33.35, 23.80, 16.75, 15.87 ppm. HRMS (ESI) calcd for C47H61N12 [M+H]+ 793.51366, found 793.51400.

Reference： [1]Tetrahedron,2014,vol. 70,p. 8758 - 8767

44
[ 767-15-7 ]
[ 72804-96-7 ]
1-amino-4,6-dimethyl-1H-pyrimidin-2-ylideneammonium diphenylphosphinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	In dichloromethane; at 0℃; for 24h;Inert atmosphere;	The solution of 2-amino-4,6-dimethylpyrimidine (4.18 g, 34.0 mmol) in dry dichloromethane (80 mL) was put under argon and cooled in an ice-^ath to 0 C. Then to the solution 8.8 g (34.0 mmol) of <strong>[72804-96-7]O-(diphenylphosphinyl)hydroxylamine</strong> were added portionwise. The resulted white suspension was stirred for 24 hours, then the mixture was slowly brought to room temperature (without removing the ice-^ath). White solid product thus formed was filtered on Schott funnel. The filtrate was concentrated, obtained yellow solid was triturated with dichloromethane and filtered-off (second crop). Combined solids were dried under reduced pressure to obtain 7.78 g of the title product (yield 64%). MS-ESI: (m/z) calculated for C6HioN4 [M+H]": 139.09, found 139.1 (iminium cation); calculated for C12H11O2P [M-H]": 217.04, found 217.1 (diphenylphosphinate anion).

Reference： [1]Patent: WO2015/177688,2015,A1 .Location in patent: Page/Page column 19; 20

45
[ 767-15-7 ]
C₂₈H₂₄Cl₄N₂O₆Zn [ No CAS ]
C₄₀H₃₈Cl₄N₈O₄Zn [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	In acetone; at 20℃; for 3h;	<strong>[767-15-7]2-Amino-4,6-dimethylpyrimidine</strong> (0.2 g, 1.62 mmol) dissolved in 20 ml of acetone and gradually added to 100 ml of stirred acetone solution of [Zn2(diclo)4] (0.5 g, 0.409 mmol). The reaction mixture was kept stirring for an additional 3 h, then left to evaporate to give 0.42 g of solid product. Yield 60percent; m.p. 155 °C (decompose); IR (cm-1, KBr): 3447, 3369,3182, 3080, 3034, 2975, 2927, 2845, 1673, 1621, 1605, 1591, 1565, 1538, 1451, 1400, 1368, 1304, 1196, 1155, 1094, 1049, 947; 1HNMR (delta, CDCl3): 2.50 (s, 6H, 2CH3(admp)), 3.70 (s, 2H, CH2), 3.93 (s,2H, NH2(admp)) 6.65 (d, 1H, CH, 3JH?H = 9 Hz), 6.71(s, 1H, CH(admp)),7.17 (m, 1H, CH, 3JH?H = 15 Hz), 7.36 (m, 1H, CH, 3JH?H = 14.4 Hz),7.43 (m, 1H, CH, 3JH?H = 17.28 Hz), 7.52 (d, 1H, CH, 3JH?H = 7.7 Hz),7.79 (d, 2H, 2CH, 3JH?H = 9 Hz), 8.85 (s, 1H, NH); 13C{1H} NMR (delta, CDCl3): 23.72 (2CH3(admp)), 40.00 (CH2), 109.08 (CH(admp)), 116.67(CH), 121.14 (CH), 124.90 (CH), 127.10 (C), 127.30 (2CH), 129.32(CH), 129.45 (2CH), 131.20 (CH), 137.93 (C), 143.20 (C), 163.72(2C(admp)), 167.17 (2C(admp)), 177.63 (C); UV?Vis (DMSO, lambda (nm)): 285.

Reference： [1]Polyhedron,2016,vol. 107,p. 97 - 106

46
[ 767-15-7 ]
[ 16712-64-4 ]
2C₁₁H₈O₃*C₆H₉N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	In ethanol; water; at 20℃; for 240h;	Slow evaporation of a 1:1 ethanol/distilledwater solution (10 mL) containing 6-hydroxy-2-naphthoic acid(0.0376 g, 0.2 mmol) and 2-amino-4,6-dimethyl pyrimidine(0.0123 g, 0.1 mmol) yielded colorless crystals of 7 after ten days.Good quality single crystals, suitable for diffraction, were gatheredfrom their mother solution by filtration and dried under vacuum.Yield: 84percent.Anal. calcd for C28H27N3O7: C, 64.99; H, 5.22; N, 8.12percent.Found: C, 65.32; H, 5.57; N, 8.36percent. Infrared spectrum (KBr disc,cm1): 3193 s, 2912 m, 2598 m, 2338 w, 1921 w, 1684 s, 1628 s,1483 s, 1438 m, 1354 s, 1285 s, 1209 s, 1152 s, 1098 m, 971 w, 868 m,814 m, 770 m, 521 m.

Reference： [1]Journal of Molecular Structure,2016,vol. 1115,p. 187 - 198

47
[ 767-15-7 ]
[ 14104-20-2 ]
[ 1663-45-2 ]
[Ag(μ-1,2-bis(diphenylphosphino)ethane)(2-amino-4,6-dimethylpyrimidine)](BF₄)}_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	In methanol; dichloromethane; at 20℃; for 6h;	General procedure: AgNO3 (0.2 mmol, 0.0339 g) was dissolved in a stirringmethanol solution (5 mL) of dppm (0.2 mmol, 0.0769 g), adding adichloromethane solution (5 mL) of phen (0.2 mmol, 0.0361 g) intothe reaction at ambient temperature. After 6 h, the mixturesolution was filtered and transferred to a beaker. Crystals of 1were obtained by slow evaporation over a week.

Reference： [1]Polyhedron,2016,vol. 112,p. 118 - 129

48
[ 767-15-7 ]
[ 1459-93-4 ]
C₂₀H₂₀N₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate at 40℃; for 2h;	20a Synthesis of Compound (8-5) Dimethyl isophthalate (7.2 g: 37 mmol) and sodium methoxide (10 g: 185 mmol) were added to a solution of 2-amino-4,6-dimethylpyrimidine (10 g: 81 mmol) in N-ethylpyrrolidone (75 mL), followed by stirring with heating at 40° C. for 2 hours. The temperature of the reaction system was decreased to room temperature. The reaction solution was poured into a 1N aqueous hydrochloric acid solution, and the solid component was collected by filtration. The crude product was recrystallized from acetonitrile to yield compound (8-5). (0432) The NMR spectrum of produced compound (8-5) is as follows. (0433) 1H-NMR (solvent: d6-DMSO, standard: tetramethylsilane) δ (ppm) 2.42 (12H, s) 7.04 (2H, s) 7.65 (1H, t) 8.11 (2H, d) 8.52 (1H, s) 10.80 (2H, s)

Reference： [1]Current Patent Assignee: FUJIFILM HOLDINGS CORP. - US2016/159750, 2016, A1 Location in patent: Paragraph 0431

49
[ 767-15-7 ]
[ 1073-70-7 ]
2-amino-5-(4'-chlorophenyl)-4,6-dimethylpyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%	With potassium carbonate; In dimethyl sulfoxide; at 25℃; for 24h;	General procedure: A mixture of the arylhydrazine hydrochlorides (1.0 mmol), aminopyridines (20.0 mmol), and potassium carbonate (415 mg, 3.0 mmol) in DMSO (10 mL) was stirred at 25 °C in air. The reactions were completed after 24 h, monitored by thin layer chromatography (TLC). Then, quenched by the addition of water, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and brine solution and dried over anhydrous MgSO4. The solvent was removed under reduced pressure to give the crude products. Purified by column chromatography over silica gel (hexane/AcOEt), the pure products were afforded.

Reference： [1]Tetrahedron,2016,vol. 72,p. 4132 - 4140

50
[ 767-15-7 ]
[ 652-36-8 ]
2C₆H₉N₃*C₈H₂F₄O₄*2H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60.53%	With water; In acetone; at 20℃; for 0.5h;	To an aqueous solution (5 mL) of tetrafluoroterephthalic acid (H2tfBDC 23.8 mg, 0.10 mmol), and then a solution of 2-amino-4,6-dimethyl pyrimidine (ADMPI, 12.3 mg, 0.10 mmol) in acetone (5 mL) was added, and the mixture was stirred at room temperature for 30 min. Then the solution was allowed to stand at room temperature for slow evaporation. Colorless, block crystals were gained after eleven days. The obtained crystals were separated from the mother solution by filtration, washed with an acetone-distilled water solution (v/v = 1: 1), and dried under vacuum. Yield: 31.5 mg (60.53percent based on H2tfBDC), m.p.: 172 °C. Elemental Anal. Calcd (percent) for C20H24F4N6O6: C, 46.11; H, 4.61; N, 16.14. Found: C, 46.32; H, 4.27; N, 15.89. IR data (KBr disc, cm-1): 3562m, 3482s, 3261m, 3087m, 2928w, 2789w, 2412w, 1954w, 1702s, 1644s, 1624s, 1527m, 1492m, 1457s, 1438m, 1379s, 1358s, 1265w, 1249m, 1131w, 1096w, 1052w, 988s, 947m, 884w, 869w, 795w, 732s, 673w, 634m, 595w, 549m, 520m, 474m.

Reference： [1]Journal of Molecular Structure,2016,vol. 1122,p. 256 - 267

51
[ 767-15-7 ]
[ 67359-63-1 ]
[ 74222-97-2 ]

Yield	Reaction Conditions	Operation in experiment
73%	In 1-methyl-pyrrolidin-2-one; at 100 - 105℃; for 18h;	(3) N-(methylcarboxy)-o-carbomethoxybenzenesulfonamide (27.9g, 0 . 1mol), DMF (100mL), 4,6-dimethyl pyrimidine-amine (13.5g, 0 . 11mol) was added to a 250 ml three-port bottle, heating to 100 °C -105 °C for 18h; distilling solvent by reduced pressure, cooling to room temperature, add water to the bottle, filtering, washing, drying to obtain 26.6g of methyl 2-(4,6-dimethylpyrimidin-2-ylcarbamoylaminosulfonyl)benzoate,content 95.7percent, the yield is 70percent. Embodiment 11 This embodiment with the embodiment 1 is characterized in that: step (3) the organic solvent in NMP (100 ml), step (3) in 2 - (4,6-dimethyl-pyrimidin-2-yl-carbamoyl amino sulfonyl) benzoic acid methyl ester in the yield of 73percent.

Reference： [1]Patent: CN103483270,2016,B .Location in patent: Paragraph 0046; 0069; 0070

52
[ 767-15-7 ]
N-(2,6-dimethoxy pyrimidin-4-yl)-4-isothiocyanatobenzenesulfonamide [ No CAS ]
N-(2,6-dimethoxypyrimidin-4-yl)-4-[3-(4,6-dimethylpyrimidin-2-yl)thioureido]benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With triethylamine; In 1,4-dioxane; for 1h;Reflux;	General procedure: A mixture of isothiocyanatobenzenesulfonamide 2 [32](0.01mol) and heterocyclic amine (0.01mol) in dioxane (30mL) containing triethylamine (0.1mL) was refluxed for 1h. The solvent was evaporated under reduced pressure and the solid obtained was filtered, washed with petroleum ether (bp 40-60°C) and crystallized from ethanol to afford the thiourea derivatives.

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 124,p. 299 - 310

53
[ 767-15-7 ]
C₇₆H₆₁Cl₄N₄O₁₆Zn₂ [ No CAS ]
C₅₀H₄₈Cl₂N₈O₈Zn [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In acetone; at 20℃; for 3h;	<strong>[767-15-7]2-Amino-4,6-dimethylpyrimidine</strong> (0.158 g, 1.28 mmol) was dissolvedin 20 ml of acetone and gradually added to 100 ml of stirredacetone solution of [Zn2(indo)4] (0.5 g, 0.321 mmol). The reactionmixture was stirred for an additional 3 h, then left to evaporateto give 0.59 g of solid product.Yield 90percent; m.p. 115?118 °C; IR (KBr, cm1): 3421, 3330, 3152,3000, 2957, 2925, 2852, 1677, 1658, 1620, 1612, 1596, 1570,1468, 1437, 1398, 1356, 1332, 1285, 1235, 1212, 1151, 1091,1071, 1034, 1015, 994, 954, 916, 845, 823, 793, 769, 753, 601,564, 484; 1H NMR (CDCl3): delta (ppm) 2.31 (s, 3H, CH3), 2.31 (s, 6H,2CH3(admp)), 3.29 (s, 2H, CH2), 3.69 (s, 3H, CH3), 5.58 (s, 2H, NH2(admp)), 6.36 (s, 1H, CH(admp)), 7.00 (s, 1H, CH), 6.69 (d, 1H, CH,3JH?H = 8.7 Hz), 6.92 (d, 1H, CH, 3JH?H = 8.7 Hz), 7.54 (d, 2H, 2CH,3JH?H = 6.9 Hz), 7.72 (d, 2H, 2CH, 3JH?H = 6.9 Hz); 13C{1H}NMR(CDCl3): delta (ppm) 13.45 (CH3), 23.67 (2CH3(admp)), 32.02 (CH2),55.73 (CH3), 101.70 (CH), 110.79 (CH(admp)), 111.50 (CH), 114.75(C), 114.91 (CH), 129.24 (2CH), 130.88 (C), 131.34 (C), 131.95(2CH), 134.16 (C), 135.55 (C), 139.29 (C), 156.03 (C), 162.47(C(admp)), 168.14 (C), 168.49 (2C(admp)), 178.10 (C); UV?Vis (DMSO, lambda (nm)): 271, 322, ESI-MS (M++H = 1002.96).

Reference： [1]Polyhedron,2016,vol. 117,p. 249 - 258

54
[ 78027-00-6 ]
[ 767-15-7 ]
[ 50-00-0 ]
4-amino-2-[(4,6-dimethylpyrimidin-2-yl)amino]methyl}-5-pyridin-3-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In tetrahydrofuran; at 20℃; for 4h;	General procedure: To asolution of corresponding compound 4 (1.92 g, 0.01 mol) intetrahydrofuran, morpholine (for 5a) (0.87 mL, 0.01 mol),thiomorpholine (for 5b) (0.94 mL, 0.01 mol), 1-(4-fluorophenyl)piperazine (for 5c) (1.80 g, 0.01 mol), 2-amino-4,6-dimethyl pyrimidine (for 5d) (1.23 g, 0.01 mol), or 6-aminopenicillanic acid (for 5e) (2.16 g, 0.01 mol) was addedin the presence of formaldehyde (37 percent, 3.72 mL, 0.05 mol)and the mixture was stirred at room temperature for 4 h.After evaporating the solvent under reduced pressure, asolid appeared.

Reference： [1]Medicinal Chemistry Research,2016,vol. 25,p. 1958 - 1970

55
[ 767-15-7 ]
[ 1885-14-9 ]
phenyl N-(4,6-dimethylpyrimidin-2-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%		A solution of 4,6-dimethylpyrimidin-2-amine (200 mg, 1.62 mmol) in THF (5 mL) was cooled to 0 °C and treated with NaH (130 mg, 3.24 mmol) under nitrogen atmosphere. The reaction mixture was stirred for 15 min and treated with phenyl chloroformate (380 mg, 2.43 mmol) at 0 °C under nitrogen atmosphere. The reaction mixture was warmed to RT and stirred for 12 h. Upon completion the reaction mixture was diluted with EtOAc, filtered through celite and concentrated in vacuo. The crude product was purified by column chromatography on silica gel (60-120 mesh) using 40percent EtOAc-hexanes eluant to give phenyl (4,6-dimethylpyrimidin-2-yl)carbamate (200 mg, 51 percent) as a white solid.1H NMR (300 MHz, CDCI3): delta = 7.91 (s, 1 H), 7.40-7.35 (m, 2H), 7.24-7.19 (m, 3H), 6.78(s, 1 H), 2.41 (s, 6H). LCMS (m/z): 244.20 [M+H]+.

Reference： [1]Patent: WO2016/131098,2016,A1 .Location in patent: Page/Page column 196
[2]Patent: WO2020/18970,2020,A1 .Location in patent: Paragraph 0320

56
[ 767-15-7 ]
tert-butyl 4-(10-bromo-2-oxo-1,2-dihydropyrimido[1,2-b]indazol-4-yl)piperidine-1-carboxylate [ No CAS ]
tert-butyl 4-{10-[(4,6-dimethylpyrimidin-2-yl)amino]-2-oxo-1,2-dihydropyrimido[1,2-b]indazol-4-yl}piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With potassium phosphate; t-BuBrettPhos; [(2-di-tert-butylphosphino-3,6-dimethoxy-2?,4?,6?-triisopropyl-1,1?-biphenyl)-2-(2?-amino-1,1?-biphenyl)]palladium(II) methanesulfonate; In tert-butyl alcohol; at 95℃; for 16h;Inert atmosphere;	Under argon, tert-butyl 4-(10-bromo-2-oxo-l,2-dihydropyrimido[l,2-b]indazol-4-yl)piperidine-l- carboxylate (150 mg, 335 muiotaetaomicron), 4,6-dimethylpyrimidin-2-amine (103 mg, 838 muiotaetaomicron), Tripotassium phosphate (99.6 mg, 469 muiotaetaomicron), tBuBrettPhos (9.75 mg, 20.1 muiotaetaomicron), and tBuBrettPhos Pd G3 (17.2 mg, 20.1 muiotaetaomicron) were dissolved in tert-Butanol (3.0 ml, 31 mmol). The mixture was stirred at 95 °C for 16 h and then purified via reverse phase chromatography (Method: Reprosil C18; 10 muiotaeta; 125x30 mm / flow: 50 ml/min / solvents: A = water (0,01percent formic acid), B = Acetonitrile / gradient 0.00-4.25 min = 20percentB, 4.50min = 30percentB, 19.00-22.50min = 100percentB, 22.75-25.00min = 20percentB) which afforded the product after drying in vacuo. The obtained amout was 109.0 mg (100 percent purity, 66 percent of theory). LC-MS (Method 1): Rt = 1.25 min; MS (ESIpos): m/z = 490 [M+H]+

Reference： [1]Patent: WO2016/173948,2016,A1 .Location in patent: Page/Page column 151

57
[ 767-15-7 ]
[ 104-87-0 ]
[ 92-44-4 ]
1,4-bis((4,6-dimethylpyrimidin-2-ylamino)(4-methylphenyl)methyl)naphthalene-2,3-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With formic acid; In neat (no solvent); at 80℃; for 1h;Green chemistry;	General procedure: A mixture of two equivalents of aldehyde, one equivalent of 2,3-dihydroxynaphthalene (0.16 g) and two equivalents of heteroaryl amine was heated at 80oC for the appropriate amount of time as indicated in Table 1. The progress of the reaction was monitored by thin-layer chromatography(TLC). After completion, the reaction mixture was cooled to room temperature and MeOH (5 mL) was added and then a precipitate was allowed to form. The precipitate was filtered,washed with methanol and dried. The crude product was stirred for 5 min in boiling MeOH and the resulting white precipitate was filtered. The product 4 thus obtained was found to be pure upon 1H and 13C NMR, mass spectra, elemental analyses, and TLC examination.

Reference： [1]Letters in Organic Chemistry,2017,vol. 14,p. 103 - 108

58
[ 767-15-7 ]
[ 100-52-7 ]
[ 92-44-4 ]
1,4-bis((4,6-dimethylpyrimidin-2-ylamino)(phenyl)methyl)naphthalene-2,3-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With formic acid; In neat (no solvent); at 80℃; for 1.91667h;Green chemistry;	General procedure: A mixture of two equivalents of aldehyde, one equivalent of 2,3-dihydroxynaphthalene (0.16 g) and two equivalents of heteroaryl amine was heated at 80oC for the appropriate amount of time as indicated in Table 1. The progress of the reaction was monitored by thin-layer chromatography(TLC). After completion, the reaction mixture was cooled to room temperature and MeOH (5 mL) was added and then a precipitate was allowed to form. The precipitate was filtered,washed with methanol and dried. The crude product was stirred for 5 min in boiling MeOH and the resulting white precipitate was filtered. The product 4 thus obtained was found to be pure upon 1H and 13C NMR, mass spectra, elemental analyses, and TLC examination.

Reference： [1]Letters in Organic Chemistry,2017,vol. 14,p. 103 - 108

59
[ 767-15-7 ]
[ 3132-99-8 ]
[ 92-44-4 ]
1,4-bis((4,6-dimethylpyrimidin-2-ylamino)(3-bromophenyl)methyl)naphthalene-2,3-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With formic acid; In neat (no solvent); at 80℃; for 0.833333h;Green chemistry;	General procedure: A mixture of two equivalents of aldehyde, one equivalent of 2,3-dihydroxynaphthalene (0.16 g) and two equivalents of heteroaryl amine was heated at 80oC for the appropriate amount of time as indicated in Table 1. The progress of the reaction was monitored by thin-layer chromatography(TLC). After completion, the reaction mixture was cooled to room temperature and MeOH (5 mL) was added and then a precipitate was allowed to form. The precipitate was filtered,washed with methanol and dried. The crude product was stirred for 5 min in boiling MeOH and the resulting white precipitate was filtered. The product 4 thus obtained was found to be pure upon 1H and 13C NMR, mass spectra, elemental analyses, and TLC examination.

Reference： [1]Letters in Organic Chemistry,2017,vol. 14,p. 103 - 108

60
[ 767-15-7 ]
[ 587-04-2 ]
[ 92-44-4 ]
1,4-bis((4,6-dimethylpyrimidin-2-ylamino)(3-chlorophenyl)methyl)naphthalene-2,3-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With formic acid; In neat (no solvent); at 80℃; for 0.916667h;Green chemistry;	General procedure: A mixture of two equivalents of aldehyde, one equivalent of 2,3-dihydroxynaphthalene (0.16 g) and two equivalents of heteroaryl amine was heated at 80oC for the appropriate amount of time as indicated in Table 1. The progress of the reaction was monitored by thin-layer chromatography(TLC). After completion, the reaction mixture was cooled to room temperature and MeOH (5 mL) was added and then a precipitate was allowed to form. The precipitate was filtered,washed with methanol and dried. The crude product was stirred for 5 min in boiling MeOH and the resulting white precipitate was filtered. The product 4 thus obtained was found to be pure upon 1H and 13C NMR, mass spectra, elemental analyses, and TLC examination.

Reference： [1]Letters in Organic Chemistry,2017,vol. 14,p. 103 - 108

61
[ 767-15-7 ]
[ 122-51-0 ]
[ 92-44-4 ]
C₁₇H₁₅N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With formic acid; In water; at 110℃; for 0.333333h;Green chemistry;	General procedure: Formic acid (98percent aqueous solution, 0.1 mmol) was added to a mixture of heteroaryl amine (1 mmol), triethylorthoformate(1 mmol), and 2,3-dihydroxynaphthalene (1 mmol). The reaction mixture was magnetically stirred on a preheated oilbath at 110°C for 20 min. The progress of the reaction was monitored by thin-layer chromatography (TLC). After completion,the reaction mixture was cooled down to room temperature, and CH3CN (5 mL) was added. The precipitate was filtered, washed with cold CH3CN, dried, and purifiedby recrystallization from ethyl acetate to give the pure products 4.

Reference： [1]Letters in Organic Chemistry,2017,vol. 14,p. 128 - 133

62
[ 767-15-7 ]
[ 64-18-6 ]
N-(4,6-dimethylpyrimidin-2-yl)formamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With NaY zeolite functionalized by sulfamic acid/Cu(OAc)2; at 20℃; for 0.25h;	General procedure: To a mixture of amine (1mmol) and NaY/SA/Cu(II) (0.01g), formic acid (5mmol, 0.19mL) was added and stirred for appropriate time at room temperature. After completion of the reaction as monitored by TLC (n-hexane/EtOAc=8/2), NaY/SA/Cu(II) catalyst was filtered and organic layer evaporated under reduced pressure to give pure product. The structure of the products was established from their physical properties and spectral (1H NMR, 13C NMR and IR) analysis and were compared with the data reported in the literature and are available as the Supporting information

Reference： [1]Chinese Chemical Letters,2017,vol. 28,p. 1767 - 1772

63
[ 767-15-7 ]
[ 97-51-8 ]
2-(4,6-dimethylpyrimidin-2-ylimino)methyl-4-nitrophenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	In methanol; for 6h;Reflux;	A methanolic solution (30 mL) of <strong>[767-15-7]2-amino-4,6-dimethylpyrimidine</strong> (0.1232 g, 1 mmol ) and 5-nitrosalicylaldehyde (0.1671 g, 1 mmol) was refluxed withconstant stirring for 6 h. Yellow solid (HL) was isolated bythe slow evaporation and recrystallized by using ethanol.

Reference： [1]Journal of Fluorescence,2017,vol. 27,p. 1801 - 1814

64
[ 767-15-7 ]
[ 122-51-0 ]
[ 762-04-9 ]
tetraethyl [(4,6-dimethylpyrimidin-2-ylamino)methylene]bis(phosphonate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With zinc(II) oxide; In neat (no solvent); at 100℃; for 0.0833333h;Microwave irradiation; Green chemistry;	General procedure: Various pyridinyl/pyrimidinyl amines (1a?1j; 1 mmol),diethyl phosphite (2; 2.2 mmol), triethyl orthoformate (3;1 mmol), and 7.5 molpercent of nano ZnO were taken in a flatbottomedflask and irradiated with microwave irradiationusing Catalyst System (CATA-4R) at 400 W. The progressof the reaction was monitored by TLC (3:2; n-hexane:ethylacetate) for every 1 min. The reaction was completed in5 min. After completion of reaction, the mixture was dissolvedin 10 cm3 of DCM and filtered to remove thecatalyst as residue. The organic layer was washed withwater (2 9 5 cm3) and the water layer was discarded. Thecombined organic mixture was washed with 5 cm3 brinesolution, dried over anhydrous Na2SO4, and concentratedunder reduced pressure; the solid obtained was washedwith cold water, air-dried, and recrystallized from ethanolto get the pure compounds.

Reference： [1]Monatshefte fur Chemie,2017,vol. 148,p. 1843 - 1851

65
[ 767-15-7 ]
[ 85-44-9 ]
[ 59007-49-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	In N,N-dimethyl-formamide; for 24h;Inert atmosphere; Reflux;	General procedure: A mixture of phthalic or naphthalic anhydride (7.3 mmol) and <strong>[767-15-7]2-amino-4,6-dimethylpyrimidine</strong> (8.1 mmol, 1 g) in dry DMF (10 mL) was refluxed under an argon atmosphere for 24 h until an orange-brown suspension formed. Then excess DMF was distilled off under reduced pressure. The residue was washed with hexane and dried in air. The product was purified by recrystallization from an appropriate solvent. N-(4,6-Dimethylpyrimidin-2-yl)phthalimide (2). Yellow crystalline compound. Yield 3.2 g (80percent), m.p. 118?120 C. Found (percent): C, 66.51; H, 4.41; N, 16.04. C14H11N3O2. Calculated (percent): C, 66.40; H, 4.38; N, 16.59. IR (Nujol mulls), /cm?1: 3366, 1673, 1608, 1580, 1266. 1H NMR (CDCl3), delta: 2.57 (s, 6 H, 2 CH3); 7.12 (s, 1 H, Pyrim); 7.79 q, 2 H, PI, J = 7.8 Hz); 7.93 (q, 2 H, PI, J = 7.9 Hz). 13C NMR (CDCl3), delta: 23.6, 119.6, 123.7, 131.6, 134.3, 152.7, 165.9, 169.2.

Reference： [1]Journal of Materials Chemistry C,2017,vol. 5,p. 10589 - 10599
[2]Russian Chemical Bulletin,2019,vol. 68,p. 1702 - 1713
Izv. Akad. Nauk, Ser. Khim.,2019,vol. 68,p. 1702 - 1713,12

66
[ 767-15-7 ]
[ 455-88-9 ]
C₁₃H₁₄N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 80℃; for 16h;	To a stirred solution of 2-fluoro-5-nitrotoluene (2 g, 12.903 mmol) in DMF (15 ml) was added 2- amino-3,5-dimethylpyrimidine (1.58 g, 12.90 mmol) and Cs2CO3 (6.2 g, 25.806 mmol) in a flask at room temperature and stirred for 16 h at 80 °C. Reaction mixture was monitored by TLC (50percent Ethyl acetate/Pet ether). After completion of the reaction, the reaction was allowed to room temperature and poured into ice water mixture and extracted with AcOEt (2 X 100 ml). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give crude 4-methyl-N-(2-methyl-4-nitrophenyl) pyrimidin-2-amine (2.2 g). The crude product was used for next step without purification. Mass: (ES+) C13H14N4O2 required 258.1; found 259.1 [M+H], HPLC/MS method 2.

Reference： [1]Patent: WO2017/191599,2017,A1 .Location in patent: Page/Page column 174

67
[ 767-15-7 ]
[ 87-51-4 ]
C₁₀H₉NO₂*C₆H₉N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 20℃; under 760.051 Torr;	Indole-3-acetic acid and <strong>[767-15-7]2-amino-4,6-dimethylpyrimidine</strong> in a (1:1) stoichiometric ratio were subjectedto manual grinding using an agate mortar and pestle for about5e7 min. After grinding crystallization were carried out in 10 mlglass vials in ethanol. The single crystals suitable for X-raydiffraction studies were obtained in 2e3 days upon slow evaporationat ambient conditions.

Reference： [1]Journal of Molecular Structure,2018,vol. 1166,p. 202 - 213

68
[ 767-15-7 ]
4-chloromethylbenzoyl isothiocyanate [ No CAS ]
1-(4-chloromethylbenzoyl)-3-(4,6-dimethylpyrimidine-2-yl)thiourea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79.3%	In tetrahydrofuran; at 60 - 65℃; for 0.05h;Microwave irradiation;	General procedure: Detailed descriptions of synthesis of related thiourea derivativeshave been previously reported [27]. A solution of 4-chloromethylbenzoyl chloride (1.5 mL, 10 mmol) in dry tetrahydrofuran(40 mL) was added dropwise to a three-necked roundbottomedflask containing potassium thiocyanate (0.98 g,10 mmol). The mixturewas refluxed at 60 C until a large amount ofwhite precipitate appears (KCl). A solution of 4-chloro-6-methoxypyrimidine-2-amine or 4, 6-dimethylpyrimidine-2-amine(10 mmol) in tetrahydrofuran (20 mL) was added and reacted inmicrowave heating 60e65 C for about 3 min. The resultingmixture was pushed into 500mL cold water and filtered off,washed with ethanol and dried in vacuo.

Reference： [1]Journal of Molecular Structure,2018,vol. 1169,p. 85 - 95

69
[ 767-15-7 ]
[ 17333-86-7 ]
2-((2-amino-4,6-dimethylpyrimidine-5yl)diazenyl)benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate; In ethanol; water; at 0 - 5℃; for 4h;	20 mmol of anthranilic acid is dissolved in hydrochloric acid:-water (1:1). The solution is then cooled to 0e5 C by stirring. Whilestirring, sodium nitrite (2 mmol) in water (10 mL) is graduallyadded to this solution. The reaction mixture is stirred for 2 h at0e5 C. The resulting diazonium salt solution is then added dropwiseto a cooled and stirred solution of <strong>[767-15-7]2-amino-4,6-dimethylpyrimidine</strong> (20 mmol) in sodium acetate (4 g) dissolvedin 20 mL ethanol:water (1:1). Stirring is continued for 4 h at 0e5 C.The precipitated products diluted with cold water, filtered off,washed with water several times, and dried. The obtained productis recrystalized from DMF-H2O mixture (Orange crystal, meltingpoint: 240 C decomposition).

Reference： [1]Journal of Molecular Structure,2018,vol. 1171,p. 906 - 914

70
[ 767-15-7 ]
isopimaric chloride [ No CAS ]
1,4a,7-trimethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene-1-carboxylic acid (4,6-dimethylpyrimidin-2-yl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35.36%	With triethylamine; In tetrahydrofuran;	General procedure: A mixture of oxalyl chloride (6 mmol)and CH2Cl2 (10 mL) was added to a solution of isopimaric acid (5 mmol) and CH2Cl2 (10 mL) at 0C. The reaction mixturewas stirred for 3 h at room temperature. The solvent and excess oxalyl chloride were removed by rotary evaporation to obtaincompound 1 as a yellow oil. The substituted amine (5 mmol) and Et3N (6 mmol) were dissolved in THF (10 mL). The mixturewas cooled at 0C, and 1 in THF (10 mL) was added dropwise. The reaction was stirred for 2?5 h, and the reaction progresswas monitored by TLC. After the reaction, the solvent was evaporated under reduced pressure, and the solid was purified viacolumn chromatography.

Reference： [1]Chemistry of Natural Compounds,2018,vol. 54,p. 695 - 700
Khim. Prir. Soedin.,2018,vol. 54,p. 589 - 593,5

71
[ 767-15-7 ]
C₁₀H₉NO₆S [ No CAS ]
sodium ((4,6-dimethylpyrimidin-2-yl)carbamoyl)((2-(ethoxycarbonyl) phenoxy)sulfonyl)amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%		General procedure: For the synthesis of 2, the solution of sulfurisocyanatidic chloride (7.2mmol) in 20mL toluene was added to the solution of 1 (6.0mmol) in 20mL toluene dropwise at room temperature. The reactant was heated to 140C and then the reaction proceeded for 18h under reflux. Subsequently, the mixture was cooled down to room temperature and remaining sulfurisocyanatidic chloride was removed under reduced pressure, together with the solvent. Without further purification, the resulting yellow oil 2 was dissolved in 10mL anhydrous acetonitrile and after that it was added slowly to 5mmol of 3, which was also dissolved in 10mL anhydrous acetonitrile beforehead in ice bath. After stirring for 24hat room temperature, acetonitrile was removed under reduced pressure and saturated sodium bicarbonate was added to product 4. Product 5 precipitated easily and it was further purified by recrystallization from petroleum ether/acetone in 1:1 ratio in high yields. 15% hydrochloric acid was added to aqueous solution of 5 under stirring and corresponding acidified product 4 precipitated out easily in high yields.