6-chloro-Nmethylpyrimidin-4-amine

1193-21-1

593-51-1

65766-32-7

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].