Dimethylcarbamoyl Chloride → 4-{2-[(3-Chlorophenyl)amino]pyrimidin-4-yl}pyridine-2-carbonitrile

Participants

Reaction Steps

500 mg (1.67 mmol) of N-(3-chloro-phenyl)-4-(N-oxido-4-pyridyl)-2-pyrimidineamine are suspended in 5 ml of acetonitrile, and 0.42 ml (4.5 mmol) of dimethylcarbamoyl chloride and 0.56 ml (4.5 mmol) of trimethylsilyl cyanide are added. After stirring for 14 hours at 60°, the reaction mixture is cooled to RT and the reaction product is isolated by filtration and washed with diethyl ether. Recrystallisation from tetrahydrofuran gives N-(3-chloro-phenyl)-4-(2-cyano-4-pyridyl)-2-pyrimidineamine in the form of yellow crystals; m.p. 221°-222°, Rf =0.6 (hexane:ethyl acetate=1:1).

Provenance & Evidence