6-chloro-Nmethylpyrimidin-4-amine Chemical Properties

Melting point:

138-142°C

Boiling point:

279.7±20.0 °C(Predicted)

Density 

1.338±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

2.50±0.10(Predicted)

form 

solid

Appearance

White to off-white Solid

InChI

InChI=1S/C5H6ClN3/c1-7-5-2-4(6)8-3-9-5/h2-3H,1H3,(H,7,8,9)

InChIKey

WZVLJUBTIWFTIE-UHFFFAOYSA-N

SMILES

C1=NC(Cl)=CC(NC)=N1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38-43

Safety Statements 

26-36/37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933599590

6-chloro-Nmethylpyrimidin-4-amine Usage And Synthesis

Synthesis

General procedure for the synthesis of 6-chloro-N-methyl-4-aminopyrimidine from 4,6-dichloropyrimidine and methylamine hydrochloride: in a 100 mL round-bottomed flask N,N-dimethylformamide (10 mL), 4,6-dichloropyrimidine (1 g, 6.71 mmol, 1.0 equiv.), cesium carbonate (4.4 g, 13.50 mmol, 2.01 equiv.) and methylamine hydrochloride (905 mg, 13.40 mmol, 2.00 eq.). The reaction mixture was stirred at 80 °C for 14 hours. After completion of the reaction, the reaction solution was diluted with 10 mL of water and extracted with ethyl acetate (4 x 10 mL). The organic layers were combined and washed once with 10 mL of water. The organic phase was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:1) as eluent. 750 mg (78% yield) of the target product 6-chloro-N-methyl-4-aminopyrimidine was finally obtained as a white solid. The product was analyzed by LC-MS to confirm: (ES, m/z): retention time RT = 0.476 min, LCMS 32: m/z = 144 [M + 1].

References

[1] European Journal of Organic Chemistry, 2014, vol. 2014, # 7, p. 1514 - 1524
[2] European Journal of Organic Chemistry, 2014, vol. 2014, # 7, p. 1514 - 1524
[3] Patent: WO2017/181177, 2017, A1. Location in patent: Paragraph 0950-0953
[4] Tetrahedron, 2007, vol. 63, # 25, p. 5394 - 5405

6-chloro-Nmethylpyrimidin-4-amine(65766-32-7)Related Product Information

• WY-14643
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• N1-(3-[(2,5,6-TRICHLOROPYRIMIDIN-4-YL)AMINO]PHENYL)-4-METHYLBENZAMIDE
• N4-benzyl-6-chloropyrimidine-4,5-diamine
• 4-(m-aminoanilino)-2,5,6-trichloropyrimidine
• N4-METHYL-6-CHLORO-5-NITROPYRIMIDIN-4-AMINE
• N-PHENYL-N'-(3-[(2,5,6-TRICHLOROPYRIMIDIN-4-YL)AMINO]PHENYL)UREA
• N-(4-CHLOROPHENYL)-N'-(3-[(2,5,6-TRICHLOROPYRIMIDIN-4-YL)AMINO]PHENYL)UREA
• 7-(4-TERT-BUTYLPHENYL)-4-CHLORO-6,7-DIHYDRO-2-(METHYLTHIO)-(5H)-PYRROLO[2,3-D]PYRIMIDINE
• 4-CHLORO-7-(3,5-DIMETHYLPHENYL)-6,7-DIHYDRO-2-(METHYLTHIO)-(5H)-PYRROLO[2,3-D]PYRIMIDINE
• 4-CHLORO-7-CYCLOHEXYL-6,7-DIHYDRO-2-(METHYLTHIO)-(5H)-PYRROLO[2,3-D]PYRIMIDINE
• N1-(3-[(2,5,6-TRICHLOROPYRIMIDIN-4-YL)AMINO]PHENYL)-4-(TRIFLUOROMETHYL)BENZENE-1-SULFONAMIDE
• N1-(3-[(2,5,6-TRICHLOROPYRIMIDIN-4-YL)AMINO]PHENYL)-4-CHLOROBENZENE-1-SULFONAMIDE
• N1-(3-[(2,5,6-TRICHLOROPYRIMIDIN-4-YL)AMINO]PHENYL)-4-FLUOROBENZAMIDE
• N1-(3-[(2,5,6-TRICHLOROPYRIMIDIN-4-YL)AMINO]PHENYL)-4-METHYLBENZENE-1-SULFONAMIDE
• 4-CHLORO-2-METHYLSULFANYL-6-PHENYLAMINO-PYRIMIDINE-5-CARBONITRILE
• 4-CHLORO-6,7-DIHYDRO-7-(4-METHOXYPHENYL)-2-(METHYLTHIO)-(5H)-PYRROLO[2,3-D]PYRIMIDINE
• N1-(3-[(2,5,6-TRICHLOROPYRIMIDIN-4-YL)AMINO]PHENYL)-3-(TRIFLUOROMETHYL)BENZAMIDE