m-Chloroperbenzoic acid → HCID 178517607, compound

Participants

Reaction Conditions

Reaction Steps

To a cold (0° C.) solution of 4-[2-(3-chlorophenyl)-7-(methylthio)pyrazolo[1,5-c]pyrimidin-3-yl]-N-cyclopentylpyrimidin-2-amine (90 mg, 0.206 mmol) in dichloromethane (10 mL) was added m-chloroperoxybenzoic acid (54 mg, 0.313 mmol). The reaction mixture was stirred 1.5 hours at 0° C. then diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate. The organic layer was washed with water and brine, then dried over magnesium sulfate. Filtration and concentration provided a crude oil. In a separate flask, a solution of sodium butoxide was prepared by reacting sodium (35 mg, 1.52 mmol) with n-butanol (2 mL). The sodium butoxide solution was added to the crude oil and the resulting solution was heated in a sealed tube at 120° C. for 16 hours. The reaction mixture was cooled and concentrated in vacuo. The resulting oil was partitioned between water and ethyl acetate. The organic layer was washed with water and brine, then dried over magnesium sulfate. Filtration and concentration provided a crude oil which was diluted with ethyl acetate (˜5 mL). Upon standing 7 hours, a solid had precipitated, which was collected on a filter to provide 2-(3-chlorophenyl)-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-c]pyrimidin-7-ol (22 mg, 26%) as a pale yellow solid. 1H NMR (CDCl3) δ 8.00 (d, 1H), 7.60 (s, 1H), 7.42 (d, 1H), 7.36 (d, 1H), 7.30 (d, 1H), 7.25 (s, 1H), 7.14 (d, 1H), 7.02 (d, 1H), 6.24 (d, 1H), 4.19 (m, 1H), 1.99 (m, 2H), 1.78–1.42 (m, 6H); MS m/z 407 (M+1).

Provenance & Evidence