m-Chloroperbenzoic acid → HCID 18753265, compound

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.

1. washwashed rapidly with 30 ml of a cold, saturated aqueous solution of sodium hydrogencarbonate
2. customThe organic phase was separated
3. dry with materialdried over sodium sulfate
4. waitAfter 18 hours at room temperature
5. customthe solution was evaporated
6. customthe residue obtained
7. customwas then chromatographed on silica gel using
8. additiona 10:1 mixture of hexane and ethyl acetate as the eluent

ORD record

ord-8f40a816621c4f5d8be81fdb3927998e

Source dataset

uspto-grants-2004_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06673795B2