m-Chloroperbenzoic acid → HCID 18753265, compound

Participants

Reaction Steps

A solution of 1.0 g (5.4 mmol) of 4,6-dichloro-2-methylsulfanyl-pyrimidine-5-carbonitrile (J. Heterocycl. Chem. 1971, 8, 445-453) in 30 ml of dichloromethane was cooled to 0° C. and treated with 1.59 g (70%, 6.4 mmol) of 3-chloro-perbenzoic acid. The reaction mixture was warmed to room temperature and stirring was continued during 3 hours (completion of the reaction was checked by TLC). For the working-up, the reaction mixture was diluted with 70 ml of dichloromethane and washed rapidly with 30 ml of a cold, saturated aqueous solution of sodium hydrogencarbonate. The organic phase was separated and dried over sodium sulfate. Thereupon, without further working-up, the solution was treated with 385 mg (5.4 mmol) of aminomethyl-cyclopropane. After 18 hours at room temperature, the solution was evaporated and the residue obtained was then chromatographed on silica gel using a 10:1 mixture of hexane and ethyl acetate as the eluent giving 450 mg (1.85 mmol, 34% of theory) of the 4,6-dichloro-2-(cyclopropyl-methyl-amino)-pyrimidine-5-carbonitrile as a white powder; MS: [M]+=243.

Provenance & Evidence