[ CAS No. 38696-21-8 ] {[proInfo.proName]}

Name: 38696-21-8|5-Bromo-N,N-dimethylpyrimidin-2-amine|98%
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Quality Control of [ 38696-21-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 38696-21-8 ]

Product Details of [ 38696-21-8 ]

CAS No. :	38696-21-8	MDL No. :	MFCD07368228
Formula :	C₆H₈BrN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NYMYGNLCILQUMT-UHFFFAOYSA-N
M.W :	202.05	Pubchem ID :	12735315
Synonyms :

Calculated chemistry of [ 38696-21-8 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	43.94
TPSA :	29.02 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.57 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.93
Log Po/w (XLOGP3) :	1.35
Log Po/w (WLOGP) :	1.31
Log Po/w (MLOGP) :	0.85
Log Po/w (SILICOS-IT) :	1.09
Consensus Log Po/w :	1.31

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.32
Solubility :	0.964 mg/ml ; 0.00477 mol/l
Class :	Soluble
Log S (Ali) :	-1.56
Solubility :	5.55 mg/ml ; 0.0274 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.62
Solubility :	0.484 mg/ml ; 0.00239 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.82

Safety of [ 38696-21-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 38696-21-8 ]

* 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 [ 38696-21-8 ]
Downstream synthetic route of [ 38696-21-8 ]

[ 38696-21-8 ] Synthesis Path-Upstream 1~9

1
[ 7752-82-1 ]
[ 74-88-4 ]
[ 31402-54-7 ]
[ 38696-21-8 ]

Yield	Reaction Conditions	Operation in experiment
20%	Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25 h; Stage #2: at 0 - 20℃; for 4.5 h;	Step 39a: 5-Bromo-N-methylpyrimidin-2-amine (compound 0601-116) and 5-bromo-N,N- dimethylpyrimidin-2-amine (compound 0601-117)A mixture of 5-bromopyrimidin-2-amine (3.48 g, 20 mmol) and DMF (20 mL) was cooled to 0°C. To the mixture NaH (60percent, 1.44 g, 36 mmol) was added. After 15 minutes, iodomethane (5 mL, 80 mmol) was added and stirred at 0°C for 0.5 h and the mixture was warmed to room temperature for additional 4 hours. Water (30 mL) was added and extracted with ethyl acetate (3 x 30 mL). The combined organic layers was washed with brine, dried over Na2S04, concentrated and purified by column chromatograph on silica gel (ethyl acetate in petroleum ether, 10percent v/v) to give two compounds: compound 0601-116 (0.76 g, 20percent) as a white solid, LCMS: 190 [M+2]⁺; ¹HNMR (400 MHz, DMSO-<3/4) δ 2.75 (d, J= 4.8 Hz, 3H), 7.35 (d, J= 4.0 Hz, 1H), 8.34 (s, 2H); compound 0601-117 (1.96 g, 49percent) as a yellow solid, LCMS: 202 [M+l]⁺; ¹HNMR (400 MHz, DMSO-<3/4) δ 3.12 (s, 6H), 8.43 (s, 2H).
20%	Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25 h; Stage #2: at 0 - 20℃; for 4.5 h;	Step 39a: 5-Bromo-N-methylpyrimidin-2-amine (compound 0601-116) and 5-bromo-N,N-dimethylpyrimidin-2-amine (compound 0601-117)[0353]A mixture of 5-bromopyrimidin-2-amine (3.48 g, 20 mmol) and DMF (20 mL) was cooled to 0° C. To the mixture NaH (60percent, 1.44 g, 36 mmol) was added. After 15 minutes, iodomethane (5 mL, 80 mmol) was added and stirred at 0° C. for 0.5 h and the mixture was warmed to room temperature for additional 4 hours. Water (30 mL) was added and extracted with ethyl acetate (3×30 mL). The combined organic layers was washed with brine, dried over Na2SO4, concentrated and purified by column chromatograph on silica gel (ethyl acetate in petroleum ether, 10percent v/v) to give two compounds: compound 0601-116 (0.76 g, 20percent) as a white solid, LCMS: 190 [M+2]⁺; ¹HNMR (400 MHz, DMSO-d₆) δ 2.75 (d, J=4.8 Hz, 3H), 7.35 (d, J=4.0 Hz, 1H), 8.34 (s, 2H); compound 0601-117 (1.96 g, 49percent) as a yellow solid, LCMS: 202 [M+1]⁺; ¹HNMR (400 MHz, DMSO-d₆) δ 3.12 (s, 6H), 8.43 (s, 2H).
20%	Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25 h; Stage #2: at 0 - 20℃; for 4.5 h;	5-bromo-pyrimidine-2-amine (3.48g, 20mmol) and a mixture of DMF (20mL) was cooled to 0 . NaH (60percent, 1.44g, 36mmol) to the mixture was added. After 15 minutes, then 0.5 hours with stirring at O ° C. was added iodoethane (5 mL, 80 mmol), the mixture was further warmed to room temperature for 4 hours. With the addition of water (30mL) and extracted with ethyl acetate (3x30mL). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated and purified by column chromatography (petroleum ether in ethyl acetate, 10percent v / v) on silica gel to give the two compounds: Compound 0601 the -116 as a white solid (0.76g, 20percent)

Reference： [1] Patent: WO2011/130628, 2011, A1, . Location in patent: Page/Page column 173
[2] Patent: US2013/102595, 2013, A1, . Location in patent: Paragraph 0352; 0353
[3] Patent: JP2015/187145, 2015, A, . Location in patent: Paragraph 0310

2
[ 7752-82-1 ]
[ 74-88-4 ]
[ 38696-21-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium hydride In tetrahydrofuran at 20℃;	[00159] Scheme 1. Preparation of relevant pyri(mi)dyl halides A-H. Key: (a) NBS, NH₄OAc, MeCN, rt, 5 min, pyr: 85-90percent; pym: quant; (b) pyr: RCHO, Na(CN)BH₃, MeCN, reflux, 1-12h (82percent, R = C₅Hn); pym: NaH, Rl, THF, rt, overnight (85percent, R = Me); (c) Me₃(Bn)NBr, f-BuONO, CH₂Br₂, rt, overnight, pyr: 77-83percent; pym: 30- 40percent; (d) pym: HI, CH₂CI₂, 0°C, 80-85percent; (e) i. NaOH, Br₂, H₂0, rt, 50-60percent, ii. POCI₃, PhNEt₂, reflux, 4h, 75-85percent, iii. HI, CH₂CI₂, 0°C, 80-85percent; (f) ROH, Na, rt, 1-12 h, quant.; (g) RZnl, CI₂Pd(PPh₃)₂, DMF/THF, rt, overnight, pyr (Br): 72percent (R = C₆H₁₃), pym (I) 81 percent, (R = C₆H₁₃); (h) alkyne, Cul, CI₂Pd(PPh₃)₂, Et₃N, MeCN, rt, 1-12 h, quant. [00161] The pyrimidyl bromides were prepared in a similar manner, beginning with bromination of 2-aminopyrimidine. N-Alkylation could not be achieved by reductive amination (presumably due to the decreased nucleophilicity of the amine) and was instead accomplished using NaH and an appropriate alkyl halide to give (B). Nonaqueous diazotization/halo-dediazoniation was used to prepare 5-bromo-2- halopyrimidines, but in diminished yield relative to the analogous reaction with the 2- aminopyridine (again, presumably due to the decreased nucleophilicity of the amine group). Alternatively, 2-pyrimidinone could serve as a precursor to 5-bromo-2- halopyrimidines (Lutz, F.; Kawasaki, T.; Soai, K. Tetrahedron-Asymmetry 2006, 17, 486.) or as a substrate for alkylation to generate 5-bromo-2-alkoxypyrimidines (D) (Kokatla, H. P.; Lakshman, M. K. Org. Lett. 2010, 12, 4478.) Introduction of an alkyne substituent at the 2-position to give ( proceeded satisfactorily under Sonogoshira conditions, but alkylation using Negishi conditions was unselective. Since reduction of the 2- alkynylpyrimidyl bromide (F) to the corresponding 2-alkyl pyrimidyl bromide (H) was complicated by competing removal of the bromine, we turned to 5-bromo-2- iodopyrimidine as a precursor for the cross coupling reactions and saw a dramatic improvement in selectivity and yields.

Reference： [1] Patent: WO2012/162818, 2012, A1, . Location in patent: Page/Page column 45-46
[2] Journal of Organic Chemistry, 2008, vol. 73, # 23, p. 9326 - 9333

3
[ 32779-36-5 ]
[ 124-40-3 ]
[ 38696-21-8 ]

Yield	Reaction Conditions	Operation in experiment
86%	at 20℃; Inert atmosphere	To a solution of 5-bromo-2-chloropyrimidine (2 g, 10.34 mmol) and dimethylamine (5 ml, 10.00 mmol) in tetrahydrofuran (2 ml_) was stirred at room temperature overnight. The solvent was removed and the residue was purified by silica gel chromatography 5percentEtOAc/PE) to give 5-bromo-N,N-dimethylpyrimidin-2-amine (1 .9 g, 8.93 mmol, 86 percent yield) as a white solid. LCMS: [M+H] 202.
3.2 g	at 20℃; for 1 h;	A mixture of 22.5 ml (45.5 mmol) solution of dimethylamine in THF, 3.0 g (15.5 mmol) 2-chloro-5-bromo-pyrimidine and ACN are stirred at RT for 1 h. The solvent is evaporated, water is added and the mixture is extracted with EtOAc. The organic phases are pooled, dried and evaporated yielding 3.2 g 5-bromo-N,N-dimethyl- pyrimidin-2-amine .

Reference： [1] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 1, p. 34 - 38
[2] Patent: WO2017/98440, 2017, A1, . Location in patent: Page/Page column 212
[3] Patent: WO2017/194453, 2017, A1, . Location in patent: Page/Page column 46

4
[ 53939-30-3 ]
[ 124-40-3 ]
[ 38696-21-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	at 20℃; for 5 h;	50 percent Aqueous solution of dimethylamine (30 ml) was added to 5-bromo-2-chloropyridine (1.79 g, 10 mmol) and the mixture was stirred at room temperature under argon atmosphere for 5 hrs. Saturated sodium bicarbonate solution (15 ml) was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with brine and dried. The solvent was distilled off under reduced pressure and the residue was dried at 40 °C under reduced pressure for 2 hrs. to give 5-bromo-2-dimethylaminopyrimidine (1.83 g, 90 percent) as colorless crystals. m.p.: 81 - 82°C; IR (Nujol): 1586, 1527 cm-1; APCI-MS m/z: 202/204 [M+H]+.
90%	at 20℃; for 5 h; Inert atmosphere	(Preparation 29) 1) 50percent Aqueous solution of dimethylamine (30 ml) was added to 5-bromo-2-chloropyridine (1.79 g, 10 mmol) and the mixture was stirred at room temperature under argon atmosphere for 5 hrs. Saturated sodium bicarbonate solution (15 ml) was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with brine and dried. The solvent was distilled off under reduced pressure and the residue was dried at 40° C. under reduced pressure for 2 hrs. to give 5-bromo-2-dimethylaminopyrimidine (1.83 g, 90percent) as colorless crystals. m.p. : 81-82° C.; IR (Nujol) : 1586, 1527 cm^-1; APCI-MSm/z: 202/204 [M+H]

Reference： [1] Patent: EP1481965, 2004, A1, . Location in patent: Page 29-30
[2] Patent: EP2959918, 2015, A1, . Location in patent: Paragraph 0111

5
[ 7752-82-1 ]
[ 74-88-4 ]
[ 31402-54-7 ]
[ 38696-21-8 ]

Yield	Reaction Conditions	Operation in experiment
20%	Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25 h; Stage #2: at 0 - 20℃; for 4.5 h;	Step 39a: 5-Bromo-N-methylpyrimidin-2-amine (compound 0601-116) and 5-bromo-N,N- dimethylpyrimidin-2-amine (compound 0601-117)A mixture of 5-bromopyrimidin-2-amine (3.48 g, 20 mmol) and DMF (20 mL) was cooled to 0°C. To the mixture NaH (60percent, 1.44 g, 36 mmol) was added. After 15 minutes, iodomethane (5 mL, 80 mmol) was added and stirred at 0°C for 0.5 h and the mixture was warmed to room temperature for additional 4 hours. Water (30 mL) was added and extracted with ethyl acetate (3 x 30 mL). The combined organic layers was washed with brine, dried over Na2S04, concentrated and purified by column chromatograph on silica gel (ethyl acetate in petroleum ether, 10percent v/v) to give two compounds: compound 0601-116 (0.76 g, 20percent) as a white solid, LCMS: 190 [M+2]⁺; ¹HNMR (400 MHz, DMSO-<3/4) δ 2.75 (d, J= 4.8 Hz, 3H), 7.35 (d, J= 4.0 Hz, 1H), 8.34 (s, 2H); compound 0601-117 (1.96 g, 49percent) as a yellow solid, LCMS: 202 [M+l]⁺; ¹HNMR (400 MHz, DMSO-<3/4) δ 3.12 (s, 6H), 8.43 (s, 2H).
20%	Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25 h; Stage #2: at 0 - 20℃; for 4.5 h;	Step 39a: 5-Bromo-N-methylpyrimidin-2-amine (compound 0601-116) and 5-bromo-N,N-dimethylpyrimidin-2-amine (compound 0601-117)[0353]A mixture of 5-bromopyrimidin-2-amine (3.48 g, 20 mmol) and DMF (20 mL) was cooled to 0° C. To the mixture NaH (60percent, 1.44 g, 36 mmol) was added. After 15 minutes, iodomethane (5 mL, 80 mmol) was added and stirred at 0° C. for 0.5 h and the mixture was warmed to room temperature for additional 4 hours. Water (30 mL) was added and extracted with ethyl acetate (3×30 mL). The combined organic layers was washed with brine, dried over Na2SO4, concentrated and purified by column chromatograph on silica gel (ethyl acetate in petroleum ether, 10percent v/v) to give two compounds: compound 0601-116 (0.76 g, 20percent) as a white solid, LCMS: 190 [M+2]⁺; ¹HNMR (400 MHz, DMSO-d₆) δ 2.75 (d, J=4.8 Hz, 3H), 7.35 (d, J=4.0 Hz, 1H), 8.34 (s, 2H); compound 0601-117 (1.96 g, 49percent) as a yellow solid, LCMS: 202 [M+1]⁺; ¹HNMR (400 MHz, DMSO-d₆) δ 3.12 (s, 6H), 8.43 (s, 2H).
20%	Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25 h; Stage #2: at 0 - 20℃; for 4.5 h;	5-bromo-pyrimidine-2-amine (3.48g, 20mmol) and a mixture of DMF (20mL) was cooled to 0 . NaH (60percent, 1.44g, 36mmol) to the mixture was added. After 15 minutes, then 0.5 hours with stirring at O ° C. was added iodoethane (5 mL, 80 mmol), the mixture was further warmed to room temperature for 4 hours. With the addition of water (30mL) and extracted with ethyl acetate (3x30mL). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated and purified by column chromatography (petroleum ether in ethyl acetate, 10percent v / v) on silica gel to give the two compounds: Compound 0601 the -116 as a white solid (0.76g, 20percent)

6
[ 506-59-2 ]
[ 32779-36-5 ]
[ 38696-21-8 ]

Reference： [1] Patent: US2004/82586, 2004, A1,
[2] Patent: WO2014/100695, 2014, A1, . Location in patent: Paragraph 00373

7
[ 5621-02-3 ]
[ 38696-21-8 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1999, vol. 72, # 11, p. 2523 - 2535

8
[ 1072-97-5 ]
[ 74-88-4 ]
[ 38696-21-8 ]

Reference： [1] Journal of Organic Chemistry, 2012, vol. 77, # 16, p. 6908 - 6916

9
[ 38696-21-8 ]
[ 56621-99-9 ]

Reference： [1] Journal of Organic Chemistry, 2012, vol. 77, # 16, p. 6908 - 6916

[ 38696-21-8 ] Synthesis Path-Downstream 1~64

1
[ 630-10-4 ]
[ 38696-21-8 ]
2-(2-Dimethylamino-pyrimidin-5-yl)-isoselenourea; hydrobromide [ No CAS ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1981,vol. 17,p. 1935 - 1938
Zhurnal Organicheskoi Khimii,1981,vol. 17,p. 2171 - 2174

2
[ 3425-46-5 ]
[ 38696-21-8 ]
[ 65007-45-6 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1980,vol. 16,p. 1963 - 1969
Zhurnal Organicheskoi Khimii,1980,vol. 16,p. 2302 - 2309

3
[ 38696-21-8 ]
[ 81033-27-4 ]

Reference： [1]Australian Journal of Chemistry,1981,vol. 34,p. 2629 - 2633

4
[ 38696-21-8 ]
[ 80849-94-1 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1981,vol. 17,p. 1926 - 1935
Zhurnal Organicheskoi Khimii,1981,vol. 17,p. 2161 - 2170

5
[ 38696-21-8 ]
C₉H₁₁ClOZn [ No CAS ]
2-(dimethylamino)-5-(4-propoxyphenyl)pyrimidine [ No CAS ]

Reference： [1]Tetrahedron Letters,1995,vol. 36,p. 563 - 566

6
[ 5621-02-3 ]
[ 38696-21-8 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1999,vol. 72,p. 2523 - 2535

Yield	Reaction Conditions	Operation in experiment
82%	With sodium hydride; In tetrahydrofuran; at 50℃;Reflux;	General procedure: To a solution of 5-bromo-2-aminopyri(mi)dine (1.0 mmol) in dry THF (2 mL) at 50C, NaH (2.2 mmol) was added slowly and the mixture was stirred until H2 evolution ceased. Alkylbromide (2.1 mmol) was then added and the reaction was refluxed overnight. The reaction was cooled, quenched with MeOH and extracted with Et20. Thecombined organics were washed with brine and dried over MgSO4. The oil obtained was passed through a plug of silica (Et20/hexanes) to obtain pure products.5-Bromo-N,N-dihexylpyridin-2-amine (8). Compound 8 was synthesized according to the general alkylation procedure listed above. 1-Bromohexane was used as thealkylbromide of choice. Yield: quantitative
4.72g (57%)		5-Bromo-2-(dimethylamino)pyrimidine. The above product (5.07g, 41.22mmol) is dissolved in glacial acetic acid (25ml) and bromine (2.15ml, 41.95mmol) is added. The mixture is stirred for 30 min. at ambient temperature and then poured into ice-water. The mixture is rendered alkaline by addition of 10M sodium hydroxide. The product is filtered off, washed with water and dried to yield 4.72g (57%). Mp 162-164 C.

9
[ 39969-56-7 ]
[ 38696-21-8 ]
2-(dimethylamino)-5-(4-propoxyphenyl)pyrimidine [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1999,vol. 72,p. 2523 - 2535

10
[ 30752-19-3 ]
[ 38696-21-8 ]
2-(dimethylamino)-5-(4-hexyloxyphenyl)pyrimidine [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1999,vol. 72,p. 2523 - 2535

11
[ 97674-02-7 ]
[ 38696-21-8 ]
[5-(1-ethoxyvinyl)pyrimidin-2-yl]dimethylamine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3705 - 3720

12
[ 114980-26-6 ]
[ 38696-21-8 ]
5-(6-methoxy-1,3-benzoxazol-2-yl)-N,N-dimethylpyrimidin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; copper(I) bromide;bis(tri-t-butylphosphine)palladium(0); In N,N-dimethyl-formamide; at 160℃; for 0.5h;Microwave irradiation;	6-Methoxy-l,3-benzoxazole (0.67 mmol), 5-bromo-izetaiV-dimethylpyrimidin-2-amine (0.80 mmol), CuBr (0.13 mmol), Cs2CO3 (0.67 mmol) and Pd(^-Bu3P)2 (0.067 mmol) in dry DMF (3 ml) was stirred 30 min at 160C in a microwave reactor. The reaction mixture was filtered through celite, washed through with CH2Cl2 and the solvents were removed under reduced pressure. The crude product was purified by flash chromatography (CH2Cl2 / CH2Cl2ZMeOH (9:1) gradient) to give the title compound as an off white solid (108.2 mg). 1HNMR delta ppm 8.99 (s, 2 H) 7.62 (d, 1 H) 7.38 (d, 1 H) 6.98 (dd, 1 H) 3.83 (s, 3 H) 3.23 (s, 6 H); MS m/z 271 (M+H).

Reference： [1]Patent: WO2007/149030,2007,A1 .Location in patent: Page/Page column 54

13
[ 38696-21-8 ]
[ 265107-46-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3705 - 3720

14
[ 38696-21-8 ]
[ 856014-61-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3705 - 3720

15
[ 38696-21-8 ]
5-(3-bromo-phenyl)-7-(2-dimethylamino-pyrimidin-5-yl)-pyrido[2,3-<i>d</i>]pyrimidin-4-ylamine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3705 - 3720

16
[ 53939-30-3 ]
[ 124-40-3 ]
[ 38696-21-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	In water; at 20℃; for 5h;	50 % Aqueous solution of dimethylamine (30 ml) was added to 5-bromo-2-chloropyridine (1.79 g, 10 mmol) and the mixture was stirred at room temperature under argon atmosphere for 5 hrs. Saturated sodium bicarbonate solution (15 ml) was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with brine and dried. The solvent was distilled off under reduced pressure and the residue was dried at 40 C under reduced pressure for 2 hrs. to give 5-bromo-2-dimethylaminopyrimidine (1.83 g, 90 %) as colorless crystals. m.p.: 81 - 82C; IR (Nujol): 1586, 1527 cm-1; APCI-MS m/z: 202/204 [M+H]+.
90%	In water; at 20℃; for 5h;Inert atmosphere;	(Preparation 29) 1) 50% Aqueous solution of dimethylamine (30 ml) was added to 5-bromo-2-chloropyridine (1.79 g, 10 mmol) and the mixture was stirred at room temperature under argon atmosphere for 5 hrs. Saturated sodium bicarbonate solution (15 ml) was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with brine and dried. The solvent was distilled off under reduced pressure and the residue was dried at 40 C. under reduced pressure for 2 hrs. to give 5-bromo-2-dimethylaminopyrimidine (1.83 g, 90%) as colorless crystals. m.p. : 81-82 C.; IR (Nujol) : 1586, 1527 cm-1; APCI-MSm/z: 202/204 [M+H]

Reference： [1]Patent: EP1481965,2004,A1 .Location in patent: Page 29-30
[2]Patent: EP2959918,2015,A1 .Location in patent: Paragraph 0111

17
[ 38696-21-8 ]
2-dimethylamino-5-pyrimidinylboric acid hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		REFERENCE EXAMPLE 1 To a solution of <strong>[38696-21-8]5-bromo-2-dimethylaminopyrimidine</strong> (2.0 g, 9.9 mmol: Bull. Chem. Soc. Jpn., 72, 2523 (1999)) dissolved in THF (25 ml) was added 1.56 M of n-butyl lithium (hexane solution, 7.0 ml, 10.9 mmol) under cooling with a dry ice-acetone bath. After stirring the mixture for 40 minutes, a solution of triisopropyl borate (3.5 ml, 0.15 ml) dissolved in THF (6 ml) was added to the reaction mixture. The temperature of the mixture was raised to room temperature, hydrochloric acid was added to the mixture, and then the solvent was removed. The residue was triturated by methanol-diethyl ether to give 2-dimethylamino-5-pyrimidinylboric acid hydrochloride (2.26 g). The compound obtained in Reference example 1 was used in the preparation of compound of Examples 21 and 22.

Reference： [1]Patent: US2006/135597,2006,A1 .Location in patent: Page/Page column 22

18
[ 30418-59-8 ]
[ 38696-21-8 ]
[ 504-63-2 ]
[ 184097-42-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine)palladium (0); In 1,2-dimethoxyethane; water;	3-(2-(Dimethylamino)-5-pyrimidyl)aniline (2h): A mixture of <strong>[38696-21-8]5-bromo-2-(dimethylamino)pyrimidine</strong> (6.76g, 33.17mmol), 3-aminophenylboronic acid hemisultat (7.4g, 39.78mmol) potassium carbonate (13.73g, 99.49mmol), 1,3-propanediol (12ml, 166mmol) and tetrakis(triphenylphosphine)palladium(0) (0.2g) in a mixture of water (30ml) and dimethoxyethane (60ml) is heated to 80 C. under nitrogen overnight. After cooling the mixture is diluted with water and ethyl acetate and is filtered through a fluted filterpaper. The layers are separated and the aqeous phase is extracted once with ethyl acetate. The combined organic phases are dried over sodium sulfate and evaporated to dryness. The residue is triturated with a mixture of ethyl acetate and petroleum ether (1:1) to leave crystalline 2h (5.26g, 74%). Mp 115.5-117 C.

Reference： [1]Patent: US5902813,1999,A

19
trans-3-[[4-(tert-butoxycarbonyl-methyl-amino)-cyclohexyl]-(3-chlorobenzo[b]thiophene-2-carbonyl)-amino]-methyl}-4-methoxy-benzeneboronic acid [ No CAS ]
[ 38696-21-8 ]
trans-3-chloro-benzo[b]thiophene-2-carboxylic acid [5-(2-dimethylamino-pyrimidin-5-yl)-2-methoxy-benzyl]-(4-methylamino-cyclohexyl)-amide dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%		3-Chloro-benzo[b]thiophene-2-carboxylic acid [5-(2-dimethylamino-pyrimidin- 5-yl)-2-methoxy-benzyl]-(4-methylamino-cyclohexyl)-amide dihydrochloride(71),NH.(HCI)2 EPO <DP n="242"/>The title compound is prepared from boronic acid 5 (25 mg, 43 mumol) and 5-bromo- 2-(dimethylamino)pyrimidine (7.2 mg, 36 mumol) in accordance with Method L2. Yield: 12.0 mg (52%).LC/MS tr 1.25 min. MS(ES+) m/z 566, 564 (M+H).; Method L2 - Synthetic Procedures Used for a Biaryl LibraryCesium carbonate (2.2 equiv.) and tetrakis(triphenylphosphine)palladium(0) (0.01 equiv.) are combined and degassed with nitrogen for 5 minutes. A solution of the boronic acid (1.2 equiv.) and aryl halide (1.0 equiv.) in toluene (3 mL) and EtOH (1 mL) is then added, the reaction mixtures degassed with nitrogen for a further 5 minutes, then warmed for 16 h at 110C (external temperature). The reactions are allowed to cool to RT then the solvents removed in vacuo. The crude residues are purified by chromatography (EtOAc in heptane) to give the intermediate Suzuki products. These are treated with a 4 M solution of HCl in 1,4-dioxane (0.5 mL) for 1 h at RT, after which the solvents are removed in vacuo. The reaction residues are then dissolved in MeOH and analysed by LC/MS. If the purity of the final compound is >50% no further purification is attempted. Thus the MeOH is simply removed in vacuo to yield the title compound. If contamination by triphenylphosphine oxide is extensive, the MeOH is removed in vacuo and the residue taken up in water (1 mL). This aqueous solution is washed with TBME (3 x 1 mL) then reduced in vacuo to afford the title compound.
52%		Method L2 - Synthetic Procedures Used for a Biaryl Library <n="110"/>Cesium carbonate (2.2 equiv.) and tetxakis(triphenylphosphine)palladium(0) (0.01 equiv.) were combined and degassed with nitrogen for 5 minutes. A solution of the boronic acid (1.2 equiv.) and aryl halide (1.0 equiv.) in toluene (3 mL) and EtOH (1 mL) was then added, the reaction mixtures degassed with nitrogen for a further 5 minutes, then warmed for 16 h at 110C (external temperature). The reactions were allowed to cool to RT then the solvents removed in vacuo. The crude residues were purified by chromatography (EtOAc in heptane) to give the intermediate Suzuki products. These were treated with a 4 M solution of HCl in 1,4- dioxane (0.5 mL) for 1 h at RT, after which the solvents were removed in vacuo. The reaction residues were then dissolved in MeOH and analysed by LC/MS. If the purity of the final compound was >50% no further purification was attempted. Thus the MeOH was simply removed in vacuo to yield the title compound. If contamination by triphenylphosphine oxide was extensive, the MeOH was removed in vacuo and the residue taken up in water (1 mL). This aqueous solution was washed with TBME (3 x 1 mL) then reduced in vacuo to afford the title compound.; Synthesis of Compound 3213-Chloro-benzo[£Jthiophene-2-carboxyIic acid [5-(2-dimethyIamino-pyrimidin- 5-yl)-2-methoxy-behzyl\|-(4-methylamino-cycIohexyl)-aniide dihydrochloride(71) <n="154"/>The title compound was prepared from boronic acid 5 (25 mg, 43 mumol) and 5- bromo-2-(dimethylamino)pyrimidine (7.2 mg, 36 mumol) in accordance with MethodL2.Yield: 12.0 mg (52%).LC/MS tr 1.25 min.MS(ES+) m/z 566, 564 (M+H).
52%		Method L2 - Synthetic Procedures Used for a Biaryl Library; Cesium carbonate (2.2 equiv.) and tetrakis(triphenylphosphine)palladium(0) (0.01 equiv.) are combined and degassed with nitrogen for 5 minutes. A solution of the boronic acid (1.2 equiv.) and aryl halide (1.0 equiv.) in toluene (3 mL) and EtOH (1 mL) is then added, the reaction mixtures degassed with nitrogen for a further 5 minutes, then warmed for 16 h at 1 100C (external temperature). The reactions are allowed to cool to RT then the solvents removed in vacuo. The crude residues are purified by chromatography (EtOAc in heptane) to give the intermediate Suzuki products. These are treated with a 4 M solution of HCl in 1,4-dioxane (0.5 mL) for 1 h at RT, after which the solvents are removed in vacuo. The reaction residues are then dissolved in MeOH and analysed by LC/MS. If the purity of the final compound is >50% no further purification is attempted. Thus the MeOH is simply removed in vacuo to yield the title compound. If contamination by triphenylphosphine oxide is extensive, the MeOH is removed in vacuo and the residue taken up in water (1 mL). This aqueous solution is washed with TBME (3 x 1 mL) then reduced in vacuo to afford the title compound.; Synthesis of Compound 321; 3-Chloro-benzo[6]thiophene-2-carboxylic acid [5-(2-dimethylamino-pyrimidin- 5-yl)-2-methoxy-benzyl]-(4-methylamino-cyc]ohexyl)-amide dihydrochloride(71); EPO <DP n="242"/>The title compound is prepared from boronic acid 5 (25 mg, 43 mumol) and 5-bromo- 2-(dimethylamino)pyrimidine (7.2 mg, 36 mumol) in accordance with Method L2. Yield: 12.0 mg (52%). LC/MS tr 1.25 min. MS(ES+) m/z 566, 564 (M+H).

Reference： [1]Patent: WO2008/57497,2008,A2 .Location in patent: Page/Page column 240-241; 196
[2]Patent: WO2007/89669,2007,A2 .Location in patent: Page/Page column 108-109; 152-153
[3]Patent: WO2008/57469,2008,A1 .Location in patent: Page/Page column 196; 240-241

20
[ 506-59-2 ]
[ 32779-36-5 ]
[ 38696-21-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In ethyl acetate; toluene;	Example III-4 In an autoclave, N,N-dimethylamine hydrochloride (2.04 g, 25 mmol), potassium carbonate (6.91 g, 50 mmol), 5-bromo-2-chloropyrimidine (4.35 g, 22.50 mmol) and toluene (25 ml) are heated at 110 C. (bath temperature) for 20 hours. Ethyl acetate (50 ml) is added to the reaction mixture, and the organic phase is then washed with water (2*50 ml), dried over sodium sulphate, filtered and concentrated. This gives 4.01 g (72% of theory) of N-(5-bromo-2-pyrimidinyl)-N,N-dimethylamine. HPLC: log P (pH 2.3)=2.20 (purity: 91%) m.p. 68-69 C.
	With potassium carbonate; In ethanol; at 120℃; for 16h;	A mixture of 5-bromo-2-chloropyrimidine (1 g, 5.18 mmol), dimethylamine hydrochloride (1.26 g, 15.6 mmol) and K2C03 (2.16 g, 15.6 mmol) in EtOH (15 mL) was heated to 120C for 16h. After cooling, the solvent was evaporated off and the residue was used for next step without further purification. LCMS (m/z): 202.1/203.1 [M+H]"7 [M+2H]+

Reference： [1]Patent: US2004/82586,2004,A1
[2]Patent: WO2014/100695,2014,A1 .Location in patent: Paragraph 00373

21
[ 111-34-2 ]
[ 38696-21-8 ]
C₁₂H₁₉N₃O [ No CAS ]

Reference： [1]Synthesis,2008,p. 887 - 890

22
[ 945996-93-0 ]
[ 38696-21-8 ]
[ 1025061-58-8 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; at 110℃; for 16.16h;	Method L2 - Synthetic Procedures Used for a Biaryl Library; Cesium carbonate (2.2 equiv.) and tetrakis(triphenylphosphine)palladium(0) (0.01 equiv.) are combined and degassed with nitrogen for 5 minutes. A solution of the boronic acid (1.2 equiv.) and aryl halide (1.0 equiv.) in toluene (3 mL) and EtOH (1 mL) is then added, the reaction mixtures degassed with nitrogen for a further 5 minutes, then warmed for 16 h at 110C (external temperature). The reactions are allowed to cool to RT then the solvents removed in vacuo. The crude residues are purified by chromatography (EtOAc in heptane) to give the intermediate Suzuki products. These are treated with a 4 M solution of HCl in 1 ,4-dioxane (0.5 mL) for 1 h at RT, after which the solvents are removed in vacuo. The reaction residues are then dissolved in MeOH and analysed by LC/MS. If the purity of the final compound is >50% no further purification is attempted. Thus the MeOH is simply removed in vacuo to yield the title compound. If contamination by triphenylphosphine oxide is extensive, the MeOH is removed in vacuo and the residue taken up in water (1 mL). This aqueous solution is washed with TBME (3 x 1 mL) then reduced in vacuo to afford the title compound.; Synthesis of Compound 321; 3-Chloro-benzo[Z>]thiophene-2-carboxylic acid [5-(2-dimethylamino-pyrimidin- 5-yl)-2-methoxy-benzyl]-(4-methylamino-cyclohexyl)-amide dihydrochloride(71); The title compound is prepared from boronic acid 5 (25 mg, 43 mumol) and 5-bromo- 2-(dimethylamino)pyrimidine (7.2 mg, 36 mumol) in accordance with Method L2. Yield: 12.0 mg (52%). LC/MS fr 1.25 min. MS(ES+) m/z 566, 564 (M+H).

Reference： [1]Patent: WO2008/57468,2008,A1 .Location in patent: Page/Page column 240-241

23
[ 7752-82-1 ]
[ 74-88-4 ]
[ 38696-21-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium hydride; In tetrahydrofuran; at 20℃;	[00159] Scheme 1. Preparation of relevant pyri(mi)dyl halides A-H. Key: (a) NBS, NH4OAc, MeCN, rt, 5 min, pyr: 85-90%; pym: quant; (b) pyr: RCHO, Na(CN)BH3, MeCN, reflux, 1-12h (82%, R = C5Hn); pym: NaH, Rl, THF, rt, overnight (85%, R = Me); (c) Me3(Bn)NBr, f-BuONO, CH2Br2, rt, overnight, pyr: 77-83%; pym: 30- 40%; (d) pym: HI, CH2CI2, 0C, 80-85%; (e) i. NaOH, Br2, H20, rt, 50-60%, ii. POCI3, PhNEt2, reflux, 4h, 75-85%, iii. HI, CH2CI2, 0C, 80-85%; (f) ROH, Na, rt, 1-12 h, quant.; (g) RZnl, CI2Pd(PPh3)2, DMF/THF, rt, overnight, pyr (Br): 72% (R = C6H13), pym (I) 81 %, (R = C6H13); (h) alkyne, Cul, CI2Pd(PPh3)2, Et3N, MeCN, rt, 1-12 h, quant. [00161] The pyrimidyl bromides were prepared in a similar manner, beginning with bromination of 2-aminopyrimidine. N-Alkylation could not be achieved by reductive amination (presumably due to the decreased nucleophilicity of the amine) and was instead accomplished using NaH and an appropriate alkyl halide to give (B). Nonaqueous diazotization/halo-dediazoniation was used to prepare 5-bromo-2- halopyrimidines, but in diminished yield relative to the analogous reaction with the 2- aminopyridine (again, presumably due to the decreased nucleophilicity of the amine group). Alternatively, 2-pyrimidinone could serve as a precursor to 5-bromo-2- halopyrimidines (Lutz, F.; Kawasaki, T.; Soai, K. Tetrahedron-Asymmetry 2006, 17, 486.) or as a substrate for alkylation to generate 5-bromo-2-alkoxypyrimidines (D) (Kokatla, H. P.; Lakshman, M. K. Org. Lett. 2010, 12, 4478.) Introduction of an alkyne substituent at the 2-position to give ( proceeded satisfactorily under Sonogoshira conditions, but alkylation using Negishi conditions was unselective. Since reduction of the 2- alkynylpyrimidyl bromide (F) to the corresponding 2-alkyl pyrimidyl bromide (H) was complicated by competing removal of the bromine, we turned to 5-bromo-2- iodopyrimidine as a precursor for the cross coupling reactions and saw a dramatic improvement in selectivity and yields.

Reference： [1]Patent: WO2012/162818,2012,A1 .Location in patent: Page/Page column 45-46
[2]Journal of Organic Chemistry,2008,vol. 73,p. 9326 - 9333
[3]European Journal of Organic Chemistry,2020

24
[ 557-21-1 ]
[ 38696-21-8 ]
[ 55338-76-6 ]

Yield	Reaction Conditions	Operation in experiment
53%	tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 86.0℃; for 4.0h;	Step B. 2-(dimethylamino)pyrimidine-5-carbonitrile <n="77"/>The compound (5-Bromo-pyrimidin-2-yl)-dimethyl-amine (202 mg, 1.0 mmol), Zn(CN)2 (82 mg, 0.7 mmol) and Pd(PPh3)4 (58 mg, 0.05 mmol) in anhydrous DMF (1.0 ml) was heated to 86C (oil bath temperature) for 4 hours, then cooled to room temperature, diluted with toluene (5 ml), washed twice with diluted NH4OH solution, brine and dried over Na2SO4, then filtered and concentrated. The residue was separated by flash chromatography (CH2CI2ZTHF = 40:1) to give 79 mg (53%) of the desired product as a white solid. 2-(dimethylamino)pyrimidine-5-carbonitrile, MS: m/z 149 (M + H)

Reference： [1]Patent: WO2009/120826,2009,A1 .Location in patent: Page/Page column 74; 75

25
[ 1461-22-9 ]
[ 38696-21-8 ]
[ 579525-47-6 ]

Yield	Reaction Conditions	Operation in experiment
74%		n-Butyl lithium (1.5 M n-hexane solution; 6.06 ml, 9.09 mmol) was added dropwise to a solution of <strong>[38696-21-8]5-bromo-2-dimethylaminopyrimidine</strong> (1.75 g, 8.66 mmol) in tetrahydrofuran (18 ml) at -78C under argon atmosphere in 15 min. The mixture was stirred at the same temperature for 2 hrs. and then tri-n-butyltin chloride (2.5 ml) was added dropwise thereto. The mixture was stirred at the same temperature for 0.5 hrs. and then at room temperature for 1 hr. To the reaction mixture were added 10% aqueous potassium fluoride (50 ml) and ethyl acetate (50 ml) in turn and the mixture was stirred at room temperature for 0.5 hrs. The organic layer was separated and washed with water and brine in turn and dried. The solvent was distilled off under reduced pressure and the residue was purified by column chromatography on amine silica gel (Chromatolex (trademark) NH) (n-hexane) to give 5-tri-n-butylstannyl-2-dimethylaminopyrimidine (2.65 g, 74 %) as a colorless oil. IR (Neat): 2955, 2925, 2870, 2853, 1569, 1519 cm-1; APCI-MS m/z: 410/412/414 [M+H]+.
74%		2) n-Butyl lithium (1.5 M n-hexane solution; 6.06 ml, 9.09 mmol) was added dropwise to a solution of <strong>[38696-21-8]5-bromo-2-dimethylaminopyrimidine</strong> (1.75 g, 8.66 mmol) in tetrahydrofuran (18 ml) at -78 C. under argon atmosphere in 15 min. The mixture was stirred at the same temperature for 2 hrs. and then tri-n-butyltin chloride (2.5 ml) was added dropwise thereto. The mixture was stirred at the same temperature for 0.5 hrs. and then at room temperature for 1 hr. To the reaction mixture were added 10% aqueous potassium fluoride (50 ml) and ethyl acetate (50 ml) in turn and the mixture was stirred at room temperature for 0.5 hrs. The organic layer was separated and washed with water and brine in turn and dried. The solvent was distilled off under reduced pressure and the residue was purified by column chromatography on amine silica gel (Chromatolex (trademark) NH) (n-hexane) to give 5-tri-n-butylstannyl-2-dimethylaminopyrimidine (2.65 g, 74%) as a colorless oil. IR (Neat) : 2955, 2925, 2870, 2853, 1569, 1519 cm-1; APCI-MS m/z: 410/412/414 [M+H]+.

Reference： [1]Patent: EP1481965,2004,A1 .Location in patent: Page 30
[2]Patent: EP2959918,2015,A1 .Location in patent: Paragraph 0111

26
[ 2942-13-4 ]
[ 38696-21-8 ]
5-(6-methoxy-1,3-benzothiazol-2-yl)-N,N-dimethylpyrimidin-2-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1976 - 1980

27
[ 32779-36-5 ]
[ 124-40-3 ]
[ 38696-21-8 ]

Yield	Reaction Conditions	Operation in experiment
86%	In tetrahydrofuran; at 20℃;Inert atmosphere;	To a solution of 5-bromo-2-chloropyrimidine (2 g, 10.34 mmol) and dimethylamine (5 ml, 10.00 mmol) in tetrahydrofuran (2 ml_) was stirred at room temperature overnight. The solvent was removed and the residue was purified by silica gel chromatography 5%EtOAc/PE) to give 5-bromo-N,N-dimethylpyrimidin-2-amine (1 .9 g, 8.93 mmol, 86 % yield) as a white solid. LCMS: [M+H] 202.
3.2 g	In tetrahydrofuran; acetonitrile; at 20℃; for 1h;	A mixture of 22.5 ml (45.5 mmol) solution of dimethylamine in THF, 3.0 g (15.5 mmol) 2-chloro-5-bromo-pyrimidine and ACN are stirred at RT for 1 h. The solvent is evaporated, water is added and the mixture is extracted with EtOAc. The organic phases are pooled, dried and evaporated yielding 3.2 g 5-bromo-N,N-dimethyl- pyrimidin-2-amine .
	With potassium carbonate; In methanol; at 20℃; for 1h;	General procedure: To a solution of compound 10 (1 mmol) in methanol was added 2 amine (1.5 mmol), and K2CO3 (1 mmol). The resulting mixture was stirred at room temperature for 1 h. After completion of the reaction (reaction monitored by TLC) the solvent was removed under vacuum, and the compound was extracted with EtOAc. The combined organic layer was dried over anhydrous Na2S04 and concentrated under reduced pressure. The crude products were purified on a silica gel column using hexane/EtOAc to get compound 11.

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 34 - 38
[2]Patent: WO2017/98440,2017,A1 .Location in patent: Page/Page column 212
[3]Patent: WO2017/194453,2017,A1 .Location in patent: Page/Page column 46
[4]Patent: WO2020/35880,2020,A1 .Location in patent: Paragraph 000138; 000184

28
[ 38696-21-8 ]
[ 1254697-45-4 ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 34 - 38

29
[ 38696-21-8 ]
[ 73183-34-3 ]
[ 1032759-30-0 ]

Yield	Reaction Conditions	Operation in experiment
60%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; 1,2-dimethoxyethane; at 150.0℃; for 0.25h;Inert atmosphere; Microwave irradiation;	A mixture of 5-bromo-N,N-dimethylpyrimidin-2-amine (0.966 g, 4.78 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (1.46 g, 5.74 mmol), PdCl2dppf(DCM) (0.114 g, 0.14 mmol) and KOAc (1.407 g, 14.34 mmol) were placed under Ar in a 20 mL microwave flask. Anhydrous 1,2-dimethoxyethane (16 mL) was added and the flask was irradiated at 150 oC for 15 minutes. The reaction was filtered through celite, concentrated and slurried in EtOAc. The reaction was filtered through celite again and the organics were concentrated and purified by column chromatography 0 to 30 % EtOAC in Hexanes. The material was isolated as a light teal solid (0.718 g, 60 % yield). 1H NMR (400 MHz, CDCl3) delta 8.59 (s, 2H), 3.21 (s, 6H), 1.31 (s, 12H).13C NMR (100 MHz, CDCl3) delta 164.1, 83.7, 77.4, 37.2, 25.2, 24.9. HRMS (EI+) m/z calculated for C12H12BN3O2 [M+H]+: 250.1721, found: 250.17189.
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 100.0℃; for 12h;Inert atmosphere;	PdCl2(dppf)-CH2Cl2 adduct (323 mg, 0.396 mmol) was added to a solution of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1 ,3,2-dioxaborolane) (1207 mg, 4.75 mmol), 5-bromo- N,N-dimethylpyrimidin-2-amine (800 mg, 3.96 mmol) and potassium acetate (1 166 mg, 1 1 .88 mmol) in 1 ,4-dioxane (10 ml_) at room temperature under an atmosphere of nitrogen. The resulting solution was stirred at 100 C for 12 hr. The reaction was filtered and the filtrate was concentrated to afford crude product.
0.6 g	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 100.0℃; for 4.5h;	A mixture of 0.5 g (2.48 mmol) 5-bromo-N,N-dimethyl-pyrimidin-2-amine, 0.8 g (3.24 mmol) bis(pinacolato)diborone, 0.6 g (6.38 mmol) KOAc, 0.2 g (0.25 mmol) (0358) Pd(dppf)CI2 * DCM and dioxane is heated to 100C for 4.5 h. After cooling to RT, the reaction mixture is filtered through a pad of Celite and evorated, water is added and the mixture is extracted with EtOAc. The organic phases are pooled, dried and evaporated The crude product is purified by FC. (0359) Yield: 0.6 g (96%), ESI-MS: m/z = 250 (M+H)+, Rt(HPLC): 0.22 min (HPLC-A)

Reference： [1]Patent: WO2017/197151,2017,A1 .Location in patent: Page/Page column 39-40
[2]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 34 - 38
[3]Patent: WO2017/98440,2017,A1 .Location in patent: Page/Page column 212
[4]Patent: WO2017/194453,2017,A1 .Location in patent: Page/Page column 46

30
[ 7752-82-1 ]
[ 74-88-4 ]
[ 31402-54-7 ]
[ 38696-21-8 ]

Yield	Reaction Conditions	Operation in experiment
20%; 49%		Step 39a: 5-Bromo-N-methylpyrimidin-2-amine (compound 0601-116) and 5-bromo-N,N- dimethylpyrimidin-2-amine (compound 0601-117)A mixture of 5-bromopyrimidin-2-amine (3.48 g, 20 mmol) and DMF (20 mL) was cooled to 0C. To the mixture NaH (60%, 1.44 g, 36 mmol) was added. After 15 minutes, iodomethane (5 mL, 80 mmol) was added and stirred at 0C for 0.5 h and the mixture was warmed to room temperature for additional 4 hours. Water (30 mL) was added and extracted with ethyl acetate (3 x 30 mL). The combined organic layers was washed with brine, dried over Na2S04, concentrated and purified by column chromatograph on silica gel (ethyl acetate in petroleum ether, 10% v/v) to give two compounds: compound 0601-116 (0.76 g, 20%) as a white solid, LCMS: 190 [M+2]+; 1HNMR (400 MHz, DMSO-<¾) delta 2.75 (d, J= 4.8 Hz, 3H), 7.35 (d, J= 4.0 Hz, 1H), 8.34 (s, 2H); compound 0601-117 (1.96 g, 49%) as a yellow solid, LCMS: 202 [M+l]+; 1HNMR (400 MHz, DMSO-<¾) delta 3.12 (s, 6H), 8.43 (s, 2H).
20%; 49%		Step 39a: 5-Bromo-N-methylpyrimidin-2-amine (compound 0601-116) and 5-bromo-N,N-dimethylpyrimidin-2-amine (compound 0601-117)[0353]A mixture of 5-bromopyrimidin-2-amine (3.48 g, 20 mmol) and DMF (20 mL) was cooled to 0 C. To the mixture NaH (60%, 1.44 g, 36 mmol) was added. After 15 minutes, iodomethane (5 mL, 80 mmol) was added and stirred at 0 C. for 0.5 h and the mixture was warmed to room temperature for additional 4 hours. Water (30 mL) was added and extracted with ethyl acetate (3×30 mL). The combined organic layers was washed with brine, dried over Na2SO4, concentrated and purified by column chromatograph on silica gel (ethyl acetate in petroleum ether, 10% v/v) to give two compounds: compound 0601-116 (0.76 g, 20%) as a white solid, LCMS: 190 [M+2]+; 1HNMR (400 MHz, DMSO-d6) delta 2.75 (d, J=4.8 Hz, 3H), 7.35 (d, J=4.0 Hz, 1H), 8.34 (s, 2H); compound 0601-117 (1.96 g, 49%) as a yellow solid, LCMS: 202 [M+1]+; 1HNMR (400 MHz, DMSO-d6) delta 3.12 (s, 6H), 8.43 (s, 2H).
20%; 49%		5-bromo-pyrimidine-2-amine (3.48g, 20mmol) and a mixture of DMF (20mL) was cooled to 0 . NaH (60%, 1.44g, 36mmol) to the mixture was added. After 15 minutes, then 0.5 hours with stirring at O C. was added iodoethane (5 mL, 80 mmol), the mixture was further warmed to room temperature for 4 hours. With the addition of water (30mL) and extracted with ethyl acetate (3x30mL). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated and purified by column chromatography (petroleum ether in ethyl acetate, 10% v / v) on silica gel to give the two compounds: Compound 0601 the -116 as a white solid (0.76g, 20%)

Reference： [1]Patent: WO2011/130628,2011,A1 .Location in patent: Page/Page column 173
[2]Patent: US2013/102595,2013,A1 .Location in patent: Paragraph 0352; 0353
[3]Patent: JP2015/187145,2015,A .Location in patent: Paragraph 0310

31
[ 1083326-28-6 ]
[ 38696-21-8 ]
[ 1351597-83-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 6977 - 6981

32
[ 99-98-9 ]
[ 38696-21-8 ]
[ 1362243-15-9 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 8306 - 8309

33
[ 99-98-9 ]
[ 38696-21-8 ]
C₁₄H₂₀N₅ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 8306 - 8309

34
[ 1072-97-5 ]
[ 74-88-4 ]
[ 38696-21-8 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 6908 - 6916

35
[ 62-53-3 ]
[ 38696-21-8 ]
[ 1392405-80-9 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 6908 - 6916

36
[ 38696-21-8 ]
[ 56621-99-9 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 6908 - 6916

37
[ 38696-21-8 ]
[ 100-46-9 ]
[ 1083329-56-9 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 6908 - 6916

38
C₁₄H₁₅BClNO₃ [ No CAS ]
[ 38696-21-8 ]
[ 1467061-19-3 ]

Yield	Reaction Conditions	Operation in experiment
58.3%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 90℃; for 1.5h;Inert atmosphere;	To a solution of 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (150 mg, 0.57 mmol) in anhydrous 1,4-dioxane (5 mL) and DMF (1 mL) was added N,N-dimethylformiminium chloride (145 mg, 1.13 mmol). The reaction mixture was stirred at room temperature for 20 minutes to give a thick solution. The reaction mixture was then treated with 2 N aqueous potassium carbonate (393 mg, 2.85 mmol), <strong>[38696-21-8]5-bromo-N,N-dimethylpyrimidin-2-amine</strong> (115 mg, 0.57 mmol) and [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (50 mg, 0.068 mmol) and degassed with nitrogen for 2 minutes. The reaction mixture was heated to 90 C. for 30 minutes. After cooling to room temperature, the solvents were removed in vacuo and the residue was purified by column chromatography on silica gel (EtOAc/petroleum ether=1:5 to 1:1) to afford 6-chloro-5-[2-(dimethylamino)pyrimidin-5-yl]-1H-indole-3-carbaldehyde (100 mg, 58.3% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 12.25 (s, 1H), 9.92 (s, 1H), 8.40 (s, 2H), 8.36 (s, 1H), 8.01 (s, 1H), 7.69 (s, 1H), 3.15 (s, 6H).

Reference： [1]Patent: US2013/267493,2013,A1 .Location in patent: Paragraph 1042

39
[ 38696-21-8 ]
[ 1581701-33-8 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 2692 - 2703

40
[ 38696-21-8 ]
2-Dimethylamino-pyrimidine-5-carboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 2692 - 2703

41
[ 67-56-1 ]
[ 201230-82-2 ]
[ 38696-21-8 ]
methyl 2-dimethylamino-5-pyrimidinecarboxylate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 2692 - 2703

42
[ 64-18-6 ]
[ 1616099-47-8 ]
[ 38696-21-8 ]
1-(3,4-dihydroisoquinolin-2(1H)-yl)-3-(3-(2-(dimethylamino)pyrimidin-5-yl)phenoxy)propan-2-ol formate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38.5%		A mixture of <strong>[38696-21-8]5-bromo-N,N-dimethylpyrimidin-2-amine</strong> (99 mg, 0,489 mmol), 1- (3,4-dihydroisoquinolin-2(lH)-yl)-3-(3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenoxy)propan-2-ol (200 mg, 0.489 mmol), Pd(dppf)Cl2 (36 mg, 0.049 mmol), K2C03 (202 mg, 1.47 mmol) in H20-dioxane (1 mL/ 3 mL) was stirred at 100 C with microwave heating for 15 min. The solvent was removed by concentration and the crude product was purified by HPLC separation to give the title compound as the formate salt (76 mg, 38.5%). 1HNMR (CH3OD, 400MHz) delta: 8.59 (s, 2H), 8.35 (br, 1H), 7.42-7.16 (m, 7H), 6.98-6.94 (m, 1H), 4.53-4.46 (m, 3H), 4.18-4.09 (m, 2H), 3.64-3.56 (m, 2H), 3.48-3.39 (m, 2H), 3.26-3.17 (m, 8H). LCMS (m/z): 405.2 [M+H]+

Reference： [1]Patent: WO2014/100695,2014,A1 .Location in patent: Paragraph 00374

43
[ 38696-21-8 ]
C₁₆H₁₉FN₄O [ No CAS ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 15654 - 15658

44
[ 38696-21-8 ]
C₁₅H₂₆BN₃O₂ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 15654 - 15658

45
[ 106-95-6 ]
[ 38696-21-8 ]
5-allyl-N,N-dimethylpyrimidin-2-amine [ No CAS ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 15654 - 15658

46
[ 38696-21-8 ]
(2R)-4-(6-(2-(dimethylamino)pyrimidin-5-yl)-1-oxoisoquinolin2(1H)-yl)-2-methyl-2-(methylsulfonyl)-N-((tetrahydro-2H-pyran-2-yl)oxy)butanamide [ No CAS ]

Reference： [1]Patent: WO2017/98440,2017,A1

47
[ 38696-21-8 ]
C₂₁H₂₅N₅O₅S [ No CAS ]

Reference： [1]Patent: WO2017/98440,2017,A1

48
[ 768-56-9 ]
[ 38696-21-8 ]
N,N-dimethyl-5-(1-phenylbutyl)pyrimidin-2-amine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 13929 - 13935

49
[ 38696-21-8 ]
5-(6-bromoimidazo[1,2-a]pyridin-3-yl)-N,N-dimethylpyrimidin-2-amine [ No CAS ]

Reference： [1]Patent: WO2017/197151,2017,A1

50
[ 38696-21-8 ]
N-(5-(3-(2-(dimethylamino)pyrimidin-5-yl)imidazo[1,2-a]pyridin-6-yl)pyridin-3-yl)benzenesulfonamide [ No CAS ]

Reference： [1]Patent: WO2017/197151,2017,A1

51
C₁₄H₂₁GeNO₃ [ No CAS ]
[ 38696-21-8 ]
C₂₀H₂₈GeN₄O₃ [ No CAS ]

Reference： [1]ACS Catalysis,2018,vol. 8,p. 9287 - 9291

52
4-ethyl-3-ethynyl-N-(3-((4-methylpiperazin-1-yl)methyl)-5-(trifluoromethyl)phenyl)benzamide [ No CAS ]
[ 38696-21-8 ]
3-((2-(dimethylamino)pyrimidin-5-yl)ethynyl)-4-ethyl-N-(3-((4-methylpiperazin-1-yl)methyl)-5-(trifluoromethyl)phenyl)-benzamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 7977 - 7990

53
tert-butyl 2-(3-acetyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazol-1-yl)acetate [ No CAS ]
[ 38696-21-8 ]
tert-butyl 2-(3-acetyl-5-(2-(dimethylamino)pyrimidin-5-yl)-1H-indazol-1-yl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; N,N-dimethyl-formamide; at 90℃; for 5h;	To a solution of 5-bromo-NN-dimethylpymidin-2-amine (125-S2, 1 equiv)in DMF/H20 (9:1, 10 vol) was added compound (125-Si, 1 equiv), K2C03 (2 equiv) and tetrakis(triphenylphosphine)palladium (0.1 equiv). The reaction mixture was stirred at 90 C for 5 hours and concentrated under reduced pressure. The remaining residue was purified by column chromatography on silica gel (eluted with DCMI MeOH) to afford compound 125-S3.

Reference： [1]Patent: WO2018/160889,2018,A1 .Location in patent: Page/Page column 560

54
[ 38696-21-8 ]
2-(3-acetyl-5-(2-(dimethylamino)pyrimidin-5-yl)-1H-indazol-1-yl)acetic acid [ No CAS ]

Reference： [1]Patent: WO2018/160889,2018,A1

55
[ 38696-21-8 ]
(1R,3S,5R)-2-(2-(3-acetyl-5-(2-(dimethylamino)pyrimidin-5-yl)-1H-indazol-1-yl)acetyl)-N-(6-bromo-3-methylpyridin-2-yl)-5-methyl-2-azabicyclo[3.1.0]hexane-3-carboxamide [ No CAS ]

Reference： [1]Patent: WO2018/160889,2018,A1

56
[ 38696-21-8 ]
1-(3-(2-(Dimethylamino)pyrimid-5-yl)phenyl)-5-(1-pyrrolyl)benzimidazole [ No CAS ]

Reference： [1]Patent: US5902813,1999,A

57
[ 38696-21-8 ]
N-(3-(2-(Dimethylamino)pyrimid-5-yl)phenyl)-2-nitro-4-(1-pyrrolyl)aniline [ No CAS ]

Reference： [1]Patent: US5902813,1999,A

58
[ 38696-21-8 ]
[ 184173-98-6 ]

Reference： [1]Patent: US5902813,1999,A

59
[ 38696-21-8 ]
[ 184174-10-5 ]

Reference： [1]Patent: US5902813,1999,A

60
[ 106-45-6 ]
[ 38696-21-8 ]
N,N-dimethyl-5-(p-tolylthio)pyrimidin-2-amine [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 5033 - 5037
Angew. Chem.,2019,vol. 131,p. 5087 - 5091,5

61
[ 2996-92-1 ]
[ 38696-21-8 ]
N,N-dimethyl-5-phenyl-2-pyrimidinamine [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2019,vol. 14,p. 3850 - 3854

62
[ 38696-21-8 ]
[ 873-74-5 ]
4-((2-(dimethylamino)pyrimidin-5-yl)amino)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos; In 1,4-dioxane; at 120℃; for 1h;Inert atmosphere; Microwave irradiation;	General procedure: A G10 microwave vial equipped with a stir-bar was charged with compound 5-bromo-2-substituted pyrimidine (0.3 mmol), amino compound (0.33 mmol), Pd2dba3 (2 mol%), XPhos (8 mol%), NaOtBu (0.42 mmol) and anhydrous 1,4-dioxane (2 ml). The reaction vial was purged with argon, and heated by microwave irradiation until its temperature was 120 C. Then, the irradiation was automatically controlled to keep the mixture at this temperature for 1h. The reaction mixture was concentrated under reduced pressure and the crude residue was purified by flash chromatography on silica gel. The purified material was dried in vacuo to afford the corresponding products.

Reference： [1]Tetrahedron Letters,2020,vol. 61

63
[ 131211-27-3 ]
[ 38696-21-8 ]
[ 76-05-1 ]
di(1-adamantyl)-6-(N,N-dimethyl)-amino-3-pyrimidynyl-phosphane trifluoroacetic acid [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2020

64
[ 38696-21-8 ]
[ 98-80-6 ]
N,N-dimethyl-5-phenyl-2-pyrimidinamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; for 6h;Reflux; Inert atmosphere;	General procedure: To a solution of 11 (8.2 mmol) in dioxane (3 mL) under nitrogen atmosphere were added tetrakis(triphenylphosphine)palladium (0.047 g, 0.41 mmol), substituted phenylboronic acid 12 (0.98 mmol), and K2CO3 dissolved in 2 mL of water. The mixture was stirred under reflux for 6 h. The reaction mixture was diluted with EtOAc, filtered through celite, and washed with water. The combined organic layer was dried over anhydrous NaoSCL and concentrated under reduced pressure. The crude products were purified on a silica gel column using hexane/EtOAc to furnish compound Ha-d.

Reference： [1]Patent: WO2020/35880,2020,A1 .Location in patent: Paragraph 000138; 000139

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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.
P244	Keep reduction valves free from grease and oil.
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.
P231 + P232	Handle under inert gas. Protect from moisture.
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:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
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.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
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. 38696-21-8 ] {[proInfo.proName]}

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[ 38696-21-8 ] Synthesis Path-Upstream 1~9

[ 38696-21-8 ] Synthesis Path-Downstream 1~64

Related Functional Groups of [ 38696-21-8 ]

Bromides

Amines

Related Parent Nucleus of [ 38696-21-8 ]

Pyrimidines

Precautionary Statements-General

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[ 38696-21-8 ]

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[ 38696-21-8 ]