Diethyl Ether → HCID 10117059, compound

Participants

Reaction Conditions

Reaction Steps

To a cold (−78° C.) solution of ethyl 7-(cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine-6-carboxylate (50 mg, 0.095 mmol) in dichloromethane (1 mL) was added diisobutylaluminum hydride (490 μL, 1.0 M in hexanes, 0.49 mmol). The reaction mixture was stirred at −78° C. for 2 hours then poured into a stirring mixture of ether and aqueous Rochelle's salt (sodium potassium tartrate) solution. The resultant mixture was stirred at room temperature for 16 hours. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water and brine. Concentration followed by flash chromatography on silica (29:1 dichloromethane:methanol) provided [7-(cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)pyrazolo-[1,5-a]pyridin-6-yl]methanol (27 mg, 59%) as a green solid. Rf 0.26 (29:1 dichloromethane:methanol); 1H NMR (300 MHz, CDCl3): δ 7.99 (d, 1H), 7.70 (d, 1H), 7.61 (m, 2H), 7.23 (d, 1H), 7.13 (t, 2H), 6.29-6.24 (m, 2H), 5.08 (d, 1H), 4.79 (s, 2H), 4.47 (broad, 1H), 4.29 (m, 1H), 2.09-1.99 (m, 4H), 1.85-1.48 (m, 12H); MS m/z 487 (M+1).

Provenance & Evidence