[ CAS No. 931-61-3 ] {[proInfo.proName]}

Name: 931-61-3|2-Methylaminopyrimidine|97%
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Quality Control of [ 931-61-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 931-61-3 ]

CAS No. :	931-61-3	MDL No. :	MFCD00234126
Formula :	C₅H₇N₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BQNXHDSGGRTFNX-UHFFFAOYSA-N
M.W :	109.13	Pubchem ID :	265776
Synonyms :

Calculated chemistry of [ 931-61-3 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.2
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	31.34
TPSA :	37.81 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.6 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.21
Log Po/w (XLOGP3) :	0.52
Log Po/w (WLOGP) :	0.33
Log Po/w (MLOGP) :	-0.31
Log Po/w (SILICOS-IT) :	0.62
Consensus Log Po/w :	0.47

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.33
Solubility :	5.07 mg/ml ; 0.0464 mol/l
Class :	Very soluble
Log S (Ali) :	-0.88
Solubility :	14.2 mg/ml ; 0.13 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.03
Solubility :	1.03 mg/ml ; 0.0094 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.26

Safety of [ 931-61-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 931-61-3 ]

* 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 [ 931-61-3 ]
Downstream synthetic route of [ 931-61-3 ]

[ 931-61-3 ] Synthesis Path-Upstream 1~3

1
[ 1722-12-9 ]
[ 74-89-5 ]
[ 931-61-3 ]

Yield	Reaction Conditions	Operation in experiment
30%	With potassium carbonate In methanol at 80℃; Sealed tube	Intermediate AT: l-methyl-5-phenyl-1H-imidazol-2-amineStep 1: Synthesis of N-methylpyrimidin-2-amineTo a solution of 2-chloropyrimidine (1 g, 8.7 mmol) in methanol (10 mL) is added a 2M solution of methylamine (13.2 mL, 26.2 mmol) in methanol, followed by K₂C0₃ (2.5 g, 18 mmol). The reaction flask is sealed and heated to 80 °C overnight. The reaction is then cooled to room temperature and concentrated to remove volatiles. The residue is partitioned between water and CH2C12. The organic layer is dried (Na₂S0₄) and concentrated to afford the title compound (290 mg, 30percent) as a brown oil.

Reference： [1] Bulletin of the Chemical Society of Japan, 1998, vol. 71, # 8, p. 1973 - 1991
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 17, p. 6626 - 6637
[3] Molecules, 2004, vol. 9, # 7, p. 520 - 526
[4] Patent: WO2011/71716, 2011, A1, . Location in patent: Page/Page column 99
[5] Journal of the American Chemical Society, 1954, vol. 76, p. 1065,1067
[6] Journal of the Chemical Society, 1953, p. 331,336
[7] Journal of Medicinal Chemistry, 2011, vol. 54, # 2, p. 472 - 484
[8] Patent: US2012/172374, 2012, A1, . Location in patent: Page/Page column 37-38
[9] Organic Letters, 2017, vol. 19, # 17, p. 4656 - 4659

2
[ 62062-31-1 ]
[ 931-61-3 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 331 - 335

3
[ 931-61-3 ]
[ 31402-54-7 ]

Reference： [1] Journal of Organic Chemistry, 1983, vol. 48, # 7, p. 1064 - 1069

[ 931-61-3 ] Synthesis Path-Downstream 1~56

1
[ 1722-12-9 ]
[ 74-89-5 ]
[ 931-61-3 ]

Yield	Reaction Conditions	Operation in experiment
30%	With potassium carbonate; In methanol; at 80℃;Sealed tube;	Intermediate AT: l-methyl-5-phenyl-1H-imidazol-2-amineStep 1: Synthesis of N-methylpyrimidin-2-amineTo a solution of 2-chloropyrimidine (1 g, 8.7 mmol) in methanol (10 mL) is added a 2M solution of methylamine (13.2 mL, 26.2 mmol) in methanol, followed by K2C03 (2.5 g, 18 mmol). The reaction flask is sealed and heated to 80 C overnight. The reaction is then cooled to room temperature and concentrated to remove volatiles. The residue is partitioned between water and CH2C12. The organic layer is dried (Na2S04) and concentrated to afford the title compound (290 mg, 30%) as a brown oil.
		Example 7 N-(1-Methyl-5-phenyl-1H-imidazol-2-yl)-3-phenyl-propionamide (90) To a solution of 2-chloropyrimidine (90a, 2.0 g, 17.5 mmol) in THF (25 mL) was added 40% CH3NH2(aq) (7.5 mL) at 0 C. The reaction mixture was stirred at 50 C. for 1.0 hour and then poured into saturated NaHCO3(aq) and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4(s) and concentrated under reduced pressure to give N-methylpyrimidin-2-amine (90b).To a microwave vial containing a solution of N-methylpyrimidin-2-amine (90b, 290 mg, 2.7 mmol) in acetonitrile (5 mL) was added 2-bromo-1-phenylethanone (714 mg, 3.6 mmol). The vial was sealed and heated in a microwave reactor at 130 C. for 20 minutes and then cooled to room temperature. The reaction mixture was treated with hydrazine hydrate (0.65 mL, 13.3 mmol) and then heated in a microwave reactor at 100 C. for 5.0 minutes. The solution was poured into water and filtered the precipitate to give 1-methyl-5-phenyl-1H-imidazol-2-ylamine (90c).To a solution of 1-methyl-5-phenyl-1H-imidazol-2-amine (90c, 52.0 mg, 0.3 mmol) in pyridine (1.0 ml) was added 3-phenyl-propionyl chloride (60.7 mg, 0.36 mmol). The reaction mixture was stirred at room temperature for 16 hours, quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4(s) and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give N-(1-Methyl-5-phenyl-1H-imidazol-2-yl)-3-phenyl-propionamide (90) : 1H NMR (500 MHz, DMSO) delta: 7.16-7.48 (m, 10H), 6.87 (s, 1H), 3.42 (s, 3H), 3.07 (t, 2H), 2.92 (t, 2H). ESI-MS: 305.7 (M+H)+.Compounds 91 was synthesized in a manner similar to that describe above and its observed ESI-MS was 309.8 (M+H)+.

Reference： [1]Bulletin of the Chemical Society of Japan,1998,vol. 71,p. 1973 - 1991
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 6626 - 6637
[3]Molecules,2004,vol. 9,p. 520 - 526
[4]Patent: WO2011/71716,2011,A1 .Location in patent: Page/Page column 99
[5]Journal of the American Chemical Society,1954,vol. 76,p. 1065,1067
[6]Journal of Medicinal Chemistry,2011,vol. 54,p. 472 - 484
[7]Patent: US2012/172374,2012,A1 .Location in patent: Page/Page column 37-38
[8]Organic Letters,2017,vol. 19,p. 4656 - 4659

2
[ 931-61-3 ]
[ 98-74-8 ]
[ 59447-02-8 ]

Reference： [1]Patent: US2410793,1940,

3
[ 931-61-3 ]
[ 74-88-4 ]
[ 5621-02-3 ]

Reference： [1]Journal of the American Chemical Society,1954,vol. 76,p. 1065,1067

4
2-amino-1-methylpyrimidin-1-ium iodide [ No CAS ]
[ 931-61-3 ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium hydroxide; In water; at 80℃; for 0.5h;	To a solution of 2-aminopyrimidine (3.00 g, 31.55 mmol) in acetone (50 mL) iodomethane (6.87 mL, 110.41 mmol) was added and reaction mixture was stirred on the oil bath at 75 C overnight. After the reaction mixture was allowed to reach rt, the resulting white precipitate was filtered off, washed with acetone (2 × 30 mL), ether (2 × 30 mL) and dissolved in ethanol (60 mL). To this a 10% solution of sodium hydroxide in water (40 mL) was added and the reaction mixture was heated at 80 C for 0.5 h upon vigorous stirring. Then the reaction mixture was poured into ice and extracted by dichloromethane (3 × 30 mL). The combined organic phases were washed with water (30 mL), brine (3 × 20 mL), dried over Na2SO4, filtered and the solvent evaporated under reduced pressure. Yield, 75% (2.59 g); colorless crystals; mp 55-59 C (60-62 C, lit [1]); IR (KBr) nu = 3260, 3114, 3045, 2951, 2903, 2859, 1578, 1538, 1461, 1389, 1363, 1272, 1219, 1176, 1151, 1103, 1070, 987, 832, 798, 780 cm-1. 1H NMR (CDCl3) delta 3.02 (d, 3H, 3J = 5.2 Hz, CH3), 5.25 (br s, 1H, NH), 6.54 (t, 1H, 3J = 4.8 Hz, Ar-H-5), 8.31 (d, 2H, 3J = 4.8 Hz, Ar-H-4, Ar-H-6); 13C NMR (DMSO-d6) delta 28.24 (CH3), 110.13, 158.30, 163.22; MS (ESI) m/z (%) = 110 (MH+, 100). HRMS for C5H8N3: calculated 110.0718; found 110.0713.

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 74,p. 23 - 30
[2]Journal of the Chemical Society,1955,p. 4035,4036
[3]Journal of Organic Chemistry,2008,vol. 73,p. 6691 - 6697

5
[ 931-61-3 ]
[ 19617-43-7 ]
[ 77420-15-6 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 331 - 335

6
[ 931-61-3 ]
[ 15781-72-3 ]
C₁₀H₁₁N₃O₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 1284 - 1287

7
[ 931-61-3 ]
[ 16182-04-0 ]
[ 77420-19-0 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 331 - 335

8
[ 931-61-3 ]
[ 5843-43-6 ]
[ 77420-17-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 331 - 335

9
[ 931-61-3 ]
[ 16341-50-7 ]

Reference： [1]Heterocycles,1984,vol. 22,p. 1195 - 1210

10
[ 931-61-3 ]
[ 84539-19-5 ]

Reference： [1]Canadian Journal of Chemistry,1984,vol. 62,p. 1176 - 1180

11
[ 931-61-3 ]
[ 31402-54-7 ]

Reference： [1]Journal of Organic Chemistry,1983,vol. 48,p. 1064 - 1069

12
[ 62062-31-1 ]
[ 931-61-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 331 - 335

13
[ 931-61-3 ]
[ 75-44-5 ]
C₆H₆ClN₃O [ No CAS ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1987,p. 112 - 113

14
[ 931-61-3 ]
[ 75-15-0 ]
[ 74-88-4 ]
[ 161694-70-8 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1998,vol. 71,p. 1973 - 1991

17
bromo-(4-methoxy-phenyl)-acetaldehyde [ No CAS ]
[ 931-61-3 ]
[ 190377-15-2 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 5781 - 5784

18
[ 931-61-3 ]
[ 51075-28-6 ]
1-methyl-2-amino-4-(phenylmethyl)imidazole [ No CAS ]

Reference： [1]Organic Letters,2006,vol. 8,p. 5781 - 5784

19
[ 931-61-3 ]
[ 51490-01-8 ]
1-methyl-5-(3,4,5-trimethoxyphenyl)-1H-imidazol-2-ylamine [ No CAS ]

Reference： [1]Organic Letters,2006,vol. 8,p. 5781 - 5784

20
[ 931-61-3 ]
[ 1204-21-3 ]
5-(2,5-dimethoxyphenyl)-1-methyl-1H-imidazol-2-ylamine [ No CAS ]

Reference： [1]Organic Letters,2006,vol. 8,p. 5781 - 5784

21
[ 931-61-3 ]
[ 70-11-1 ]
1-methyl-5-phenyl-1H-imidazol-2-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%		Step 2: Synthesis of l-methyl-5-phenyl-1H-imidazol-2-amineTo a microwave vial containing a solution of <strong>[931-61-3]N-methylpyrimidin-2-amine</strong> (290 mg, 2.7 mmol) in acetonitrile (5 mL) is added 2-bromo-1-phenylethanone (714 mg, 3.6 mmol). The vial is sealed and heated in a microwave reactor at 130C for 20 minutes and is cooled to room temperature. The mixture is treated with hydrazine hydrate (0.65 mL, 13.3 mmol) and is then heated in a microwave reactor at 100 C for 5 minutes. The reaction is poured into water (30 mL) and filtered to afford the title compound (192 mg, 42%) as a solid.
		Example 7 N-(1-Methyl-5-phenyl-1H-imidazol-2-yl)-3-phenyl-propionamide (90) To a solution of 2-chloropyrimidine (90a, 2.0 g, 17.5 mmol) in THF (25 mL) was added 40% CH3NH2(aq) (7.5 mL) at 0 C. The reaction mixture was stirred at 50 C. for 1.0 hour and then poured into saturated NaHCO3(aq) and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4(s) and concentrated under reduced pressure to give <strong>[931-61-3]N-methylpyrimidin-2-amine</strong> (90b).To a microwave vial containing a solution of <strong>[931-61-3]N-methylpyrimidin-2-amine</strong> (90b, 290 mg, 2.7 mmol) in acetonitrile (5 mL) was added 2-bromo-1-phenylethanone (714 mg, 3.6 mmol). The vial was sealed and heated in a microwave reactor at 130 C. for 20 minutes and then cooled to room temperature. The reaction mixture was treated with hydrazine hydrate (0.65 mL, 13.3 mmol) and then heated in a microwave reactor at 100 C. for 5.0 minutes. The solution was poured into water and filtered the precipitate to give 1-methyl-5-phenyl-1H-imidazol-2-ylamine (90c).To a solution of 1-methyl-5-phenyl-1H-imidazol-2-amine (90c, 52.0 mg, 0.3 mmol) in pyridine (1.0 ml) was added 3-phenyl-propionyl chloride (60.7 mg, 0.36 mmol). The reaction mixture was stirred at room temperature for 16 hours, quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4(s) and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give N-(1-Methyl-5-phenyl-1H-imidazol-2-yl)-3-phenyl-propionamide (90) : 1H NMR (500 MHz, DMSO) delta: 7.16-7.48 (m, 10H), 6.87 (s, 1H), 3.42 (s, 3H), 3.07 (t, 2H), 2.92 (t, 2H). ESI-MS: 305.7 (M+H)+.Compounds 91 was synthesized in a manner similar to that describe above and its observed ESI-MS was 309.8 (M+H)+.

Reference： [1]Organic Letters,2006,vol. 8,p. 5781 - 5784
[2]Patent: WO2011/71716,2011,A1 .Location in patent: Page/Page column 99
[3]Patent: US2012/172374,2012,A1 .Location in patent: Page/Page column 37-38

22
[ 931-61-3 ]
[ 70-11-1 ]
1-methyl-2-phenyl-1H-imidazo[1,2-a]pyrimidin-4-ylium; bromide [ No CAS ]

Reference： [1]Organic Letters,2006,vol. 8,p. 5781 - 5784

23
[ 931-61-3 ]
[ 70-11-1 ]
2-hydroxy-1-methyl-2-phenyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ylium; bromide [ No CAS ]

Reference： [1]Organic Letters,2006,vol. 8,p. 5781 - 5784
[2]Journal of Medicinal Chemistry,2011,vol. 54,p. 472 - 484

24
[ 931-61-3 ]
Methyl-pyrimidin-2-yl-trifluoromethyl-amine [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1998,vol. 71,p. 1973 - 1991

25
[ 931-61-3 ]
[ 161694-86-6 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1998,vol. 71,p. 1973 - 1991

26
[ 931-61-3 ]
(4-Bromo-phenyl)-[2-(methyl-trifluoromethyl-amino)-pyrimidin-5-yl]-methanol [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1998,vol. 71,p. 1973 - 1991

27
[ 931-61-3 ]
2-(Methyl-trifluoromethyl-amino)-pyrimidine-5-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1998,vol. 71,p. 1973 - 1991

28
[ 931-61-3 ]
[ 77420-17-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 331 - 335

29
[ 931-61-3 ]
[ 77420-21-4 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 331 - 335

30
[ 931-61-3 ]
(4-butyl-pyrimidin-2-yl)-dimethyl-amine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1954,vol. 76,p. 1065,1067

31
[ 931-61-3 ]
(4,6-dibutyl-pyrimidin-2-yl)-dimethyl-amine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1954,vol. 76,p. 1065,1067

32
[ 931-61-3 ]
[ 136598-92-0 ]
[ 145942-74-1 ]

Yield	Reaction Conditions	Operation in experiment
	With chlorine;	Working Example 62 Using bis[(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)-2-butyl]disulfide (2.0 g), chlorine (0.25 g) and <strong>[931-61-3]2-methylaminopyrimidine</strong> (1.54 g), substantially the same reaction as in Working Example 15 was allowed to proceed to give N-methyl-N-(2-pyrimidinyl)-[(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)-2-butane]sulfonamide (Compound 77, 0.11 g) as a colorless prism. m.p. 150-151 C. IRnu cm-1 (KBr): 1616, 1564, 1508, 1442, 1396, 1349, 1199 hu 1H-NMR(CDCl3) delta: 1.21(3H,d,J=7 Hz), 3.59(3H,s), 5.08(1H,s), 5.15(1H,q,J=7 Hz), 5.19(1H,dd,J=15 Hz,J=6 Hz), 5.32(1H,d,J=15 Hz), 6.70-6.83(2H,m), 7.06(1H,t,J=4.8 Hz), 7.38(1H,m), 7.68(1H,s), 7.97(1H,s), 8.63(1H,d,J=4.8 Hz)

Reference： [1]Patent: US5389663,1995,A

33
bromo-(4-methoxy-phenyl)-acetaldehyde [ No CAS ]
[ 931-61-3 ]
Br^(1-)*C₁₄H₁₄N₃O⁽¹⁺⁾ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 6691 - 6697
[2]Journal of Heterocyclic Chemistry,2017,vol. 54,p. 121 - 124

34
[ 931-61-3 ]
[ 915278-14-7 ]
Br^(1-)*C₁₅H₁₆N₃O⁽¹⁺⁾ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 6691 - 6697
[2]Synthesis,2008,p. 2083 - 2088

35
[ 931-61-3 ]
[ 51075-28-6 ]
[ 1067227-75-1 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 6691 - 6697
[2]Synthesis,2008,p. 2083 - 2088

36
[ 931-61-3 ]
[ 20099-89-2 ]
Br^(1-)*C₁₄H₁₁N₄⁽¹⁺⁾ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 6691 - 6697

37
[ 931-61-3 ]
[ 99-81-0 ]
[ 1040373-72-5 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 6691 - 6697

38
[ 931-61-3 ]
[ 536-38-9 ]
Br^(1-)*C₁₃H₁₁ClN₃⁽¹⁺⁾ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 6691 - 6697

39
[ 931-61-3 ]
[ 403-29-2 ]
[ 1040373-73-6 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 6691 - 6697

40
[ 931-61-3 ]
[ 1067227-77-3 ]
Br^(1-)*C₁₅H₁₄N₃O₂⁽¹⁺⁾ [ No CAS ]

Reference： [1]Synthesis,2008,p. 2083 - 2088

41
[ 931-61-3 ]
[ 51075-28-6 ]
[ 1067227-75-1 ]
[ 1067227-74-0 ]

Reference： [1]Synthesis,2008,p. 2083 - 2088
[2]Synthesis,2008,p. 2083 - 2088

42
[ 931-61-3 ]
[ 51075-28-6 ]
[ 1067227-74-0 ]

Reference： [1]Synthesis,2008,p. 2083 - 2088

43
[ 931-61-3 ]
[ 787586-57-6 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 472 - 484

44
[ 931-61-3 ]
[ 787586-65-6 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 472 - 484

45
[ 931-61-3 ]
[ 536-38-9 ]
[ 1040373-75-8 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 472 - 484

46
[ 931-61-3 ]
[ 2227-64-7 ]
[ 1040373-81-6 ]

Yield	Reaction Conditions	Operation in experiment
82%	With dmap; In acetonitrile; at 50℃; for 15h;	To a solution of <strong>[931-61-3]N-methylpyrimidin-2-amine</strong> (18, 1.83 g, 16.78 mmol) and 2-bromo-3-nitroacetophenone (4.10 g, 16.78 mmol) in acetonitrile (50 mL) 4-dimethylaminopyridine (20.5 mg, 0.168 mmol) was added. After being stirred at 50 C for 15 h, the reaction mixture was filtered, washed with acetonitrile (3 × 10 mL) and dried. Yield, 82% (4.83 g); white solid; mp 230-233 C; IR (KBr) nu = 3116, 3008, 2868, 1636, 1569, 1530, 1449, 1406, 1349, 1311, 1288, 1252, 1229, 1153, 1121, 1094, 1078, 1048, 996, 909, 867, 809, 762 cm-1. 1H NMR (DMSO-d6) delta 4.80 (d, 1H, 2J = 14.4 Hz, HA from CH2), 4.95 (d, 1H, 2J = 14.4 Hz, HB from CH2), 7.37 (dd, 1H, 3J1 = 6.4 Hz, 3J2 = 4.8 Hz, Ar-H-6), 7.82 (t, 1H, 3J = 8.0 Hz, Ar-H-5'), 8.15 (s, 1H, OH), 8.18-8.21 (m, 1H, Ar-H-4'/6'), 8.33-8.36 (m, 1H, Ar-H-4'/6'), 8.59 (t, 1H, 4J = 2.0 Hz, Ar-H-2'), 8.94 (dd, 1H, 3J = 6.4 Hz, 4J = 2.0 Hz, Ar-H-5/7), 9.10 (dd, 1H, 3J = 4.8 Hz, 4J = 2.0 Hz, Ar-H-5/7); 13C NMR (DMSO-d6) delta 26.29, 62.82, 90.45, 112.05, 122.48, 124.77, 130.88, 134.05, 140.71, 148.48, 148.76, 155.45, 168.18; MS (ESI) m/z (%) = 273 ([M-Br]+, 100). HRMS for C13H13N4O3: calculated 273.0988; found 273.0984.
	With dmap; In acetonitrile; at 80℃; for 0.5h;Sealed vial; Microwave irradiation;	General procedure: All 1-substituted 2-hydroxy-2-aryl-2,3-dihydro-imidazo[1,2-a]pyrimidinium salts were synthesized by using previously described protocols.41 A general procedure is described below (with compound 79 as an example): In a 30 mL microwave vial were successively brought acetonitrile (15 mL), N-(1,3-benzodioxol-5-ylmethyl)pyrimidin-2-amine (1.15 g, 5 mmol), 4-fluorophenacylbromide (1.3 g, 6 mmol, 1.2 equiv), and a catalytic amount of4-dimethylaminopyridine (6 mg, 0.05 mmol). The reaction tube was sealed and irradiated in a microwave reactor at a ceiling temperature of 80 C at 150 W maximum power for 30 min. After the reaction mixture was cooled with an air flow for 15 min, the precipitate was washed with acetone (25 mL), ether (20 mL) and dried in vacuum to afford 79 (1.98 g, 89% yield) as a white powder.

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 74,p. 23 - 30
[2]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 3462 - 3473

47
[ 931-61-3 ]
[ 1448858-08-9 ]
[ 1448858-09-0 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 6626 - 6637

48
[ 931-61-3 ]
[ 700-16-3 ]
N-methyl-5-(perfluoropyridin-4-yl)pyrimidin-2-amine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 2520 - 2523

49
[ 931-61-3 ]
[ 45715-16-0 ]

Reference： [1]Organic Letters,2016,vol. 18,p. 1976 - 1979

50
[ 931-61-3 ]
(7S)-3-(2-bromoacetyl)-7-methyl-5-[4-(trifluoromethyl)phenyl]-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one [ No CAS ]
C₁₈H₁₇F₃N₆O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%		Example 7(15) A mixture of 1-76 (220 mg, 0.528 mmol), <strong>[931-61-3]2-methylaminopyrimidine</strong> (58 mg, 0.528 mmol) and 4-(dimethylamino)pyridine (0.6 mg, 0.005 mmol) in acetonitrile (2 mL) was stirred at 85 C for 16 h. Then, hydrazine hydrate (179 mu, 3.7 mmol) was added and the mixture was stirred at 100 C for 10 min under microwave irradiation. Then, the solvent was evaporated in vacuo and the crude product was purified by flash column chromatography (silica; MeOH in DCM 0/100 to 10/90). The desired fractions were collected and the solvents evaporated in vacuo to yield Co. No. 15 (135 mg, 65%) as a yellow solid. 1H NMR (500 MHz, CDC13) delta ppm 1.70 (d, J=6.4 Hz, 3 H) 2.94 (s, 3 H) 3.96 (dd, J=12.6, 7.4 Hz, 1 H) 4.23 (dd, J=12.6, 4.2 Hz, 1 H) 4.26 (br. s., 1 H) 4.66 - 4.75 (m, 1 H) 7.07 (s, 1 H) 7.51 (d, J=8.4 Hz, 2 H) 7.75 (d, J=8.4 Hz, 2 H) 7.83 (s, 1 H) 11.10 (br. s., 1 H).

Reference： [1]Patent: WO2016/87487,2016,A1 .Location in patent: Page/Page column 78; 79

51
[ 931-61-3 ]
[ 98-88-4 ]
[ 1272665-71-0 ]

Reference： [1]Organic Letters,2017,vol. 19,p. 4656 - 4659

52
[ 931-61-3 ]
N-(3-hydroxy-5-(methyl(pyrimidin-2-yl)amino)phenyl)benzamide [ No CAS ]

Reference： [1]Archiv der Pharmazie,2019,vol. 352

53
[ 931-61-3 ]
C₁₂H₁₄N₄O [ No CAS ]

Reference： [1]Archiv der Pharmazie,2019,vol. 352

54
[ 931-61-3 ]
C₁₉H₁₈N₄O₂ [ No CAS ]

Reference： [1]Archiv der Pharmazie,2019,vol. 352

55
[ 931-61-3 ]
[ 16618-67-0 ]
C₁₂H₁₂N₄O₃ [ No CAS ]

Reference： [1]Archiv der Pharmazie,2019,vol. 352

56
[ 931-61-3 ]
[ 106662-93-5 ]
1-methyl-5-(2,4,5-trimethylphenyl)imidazol-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: N-methylpyrimidin-2-amine; 2-bromo-1-(2,4,5-trimethylphenyl)ethanone In acetonitrile at 130℃; for 0.25h; Microwave irradiation; Stage #2: With hydrazine hydrate In acetonitrile at 10 - 100℃; for 0.0833333h; Microwave irradiation;	1 Intermedate B, 2-bromo-l-(2,4,5-trimethylphenyl)ethanone (500 mg, 2.07 mmol, 1.2 eq), and /V-methylpyrimidin-2-amine (189 mg, 1.73 mmol, 1.0 eq) were taken up into a microwave tube in MeCN (2.0 mL). The reaction mixture was stirred at 130 °C for 15 mins under microwave. After cooling to 10 °C, INkH^LLO (721 mg, 8.64 mmol, 700 //L, 60% purity, 5.0 eq) was taken up into the microwave tube. The reaction mixture was heated at 100 °C for 5 mins under microwave. After completion, the reaction mixture was diluted with H2O (5.0 mL) and extracted with ethyl acetate (3 x 10 mL). The combined organic layers were washed with saturated brine (30.0 mL), dried over NaiSCri, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (S1O2, petroleum ether: ethyl acetate = 3: 1 to ethyl acetate: methanol = 20:1). Compound l-methyl-5-(2,4,5- trimethylphenyl)imidazol-2-amine (330 mg, 1.49 mmol, 86% yield, 97% purity) was obtained as yellow solid.

Reference： [1]Current Patent Assignee: MIRATI THERAPEUTICS, INC. - WO2020/167952, 2020, A1 Location in patent: Paragraph 0144

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P378
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Physical hazards
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H204	Fire or projection hazard
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Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
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H311	Toxic in contact with skin
H312	Harmful in contact with skin
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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
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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. 931-61-3 ] {[proInfo.proName]}

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[ 931-61-3 ] Synthesis Path-Upstream 1~3

[ 931-61-3 ] Synthesis Path-Downstream 1~56

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Amines

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Pyrimidines

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