Cyclopentylamine → HCID 10407742, compound

Participants

Reaction Conditions

Reaction Steps

To a cold (0° C.) solution of {3-[2-(methylthio)pyrimidin-4-yl]pyrazolo[1,5-a]pyridin-2-yl}(phenyl)methanol (294 mg, 0.844 mmol) in dichloromethane (30 mL) was added m-chloroperoxybenzoic acid (218 mg, 1.26 mmol). The reaction mixture was stirred for 1.5 hours at 0° C., then diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate solution. The organic layer was dried over magnesium sulfate, then filtered and concentrated. The resulting solid was heated in cyclopentylamine (2 mL, 20 mmol) at 45° C. for 16 hours. Concentration and flash chromatography (59:1 dichloromethane:methanol) provided {3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}(phenyl)methanol (120 mg, 89%) as a light yellow solid. Rf 0.55 (29:1 dichloromethane:methanol); 1H NMR (CDCl3) δ 8.50 (d, 1H), 8.22 (d, 1H), 7.96 (br, 1H), 7.82 (d, 1H), 7.40 (d, 2H), 7.35–7.17 (m, 4H), 6.85 (t, 1H), 6.78 (d, 1H), 6.20 (s, 1H), 5.12 (s, 1H), 4.29 (m, 1H), 2.05 (m, 2H), 1.79–1.60 (m, 4H), 1.49 (m, 2H); MS m/z 386 (M+1).

Provenance & Evidence