4-Pyrimidinamine, 2-chloro-N-methyl- (9CI) Chemical Properties

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

Appearance

White to off-white Solid

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-37/38-41-43

Safety Statements 

26-36/37-39

HS Code 

29335990

4-Pyrimidinamine, 2-chloro-N-methyl- (9CI) Usage And Synthesis

Synthesis

Synthesis of 2-chloro-N-methylpyrimidin-4-amine (18): 2,4-dichloropyrimidine (5.0 g, 33.79 mmol) was dissolved in anhydrous THF (50 mL), and a THF solution of 2.0 M methylamine (42.2 mL, 84.48 mmol) was slowly added at -40 °C. The reaction mixture was stirred at 0 °C for 4 hours. After completion of the reaction, the mixture was partitioned between CHCl3/2-propanol (4:1) and water. The organic layer was dried over anhydrous sodium sulfate, filtered through a CELITE pad and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: 100% dichloromethane) to afford 2-chloro-N-methylpyrimidin-4-amine (2.8 g, 58% yield) as a white solid. Retention time (Rt) = 1.15 min; 1H NMR (600 MHz, DMSO-d6) δ 8.02 (s, 1H), 6.22 (m, 1H), 2.86 (d, J=4.8 Hz, 3H) ppm; mass spectrum (MS) m/z: 144.12 [M+1].

References

[1] Patent: WO2016/23014, 2016, A2. Location in patent: Paragraph 00412-00413
[2] Patent: US2010/261727, 2010, A1. Location in patent: Page/Page column 30
[3] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 13, p. 3510 - 3513
[4] Patent: WO2009/97474, 2009, A1. Location in patent: Page/Page column 26-27
[5] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 5, p. 1349 - 1356

4-Pyrimidinamine, 2-chloro-N-methyl- (9CI)(66131-68-8)Related Product Information

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