Potassium Carbonate → N-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-c]pyrimidin-7-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-[7-(cyclopentylamino)-2-(4-fluorophenyl)pyrazolo[1,5-c]pyrimidin-3-yl]-3-(dimethylamino)prop-2-en-1-one (160 mg, 0.41 mmol) in N,N-dimethylformamide (10 mL) was added N-cyclopentylguanidine hydrochloride (130 mg, 0.82 mmol). Freshly ground anhydrous potassium carbonate (56 mg, 0.41 mmol) was added and the reaction heated to 140° C. for 4 hours. Additional freshly ground anhydrous potassium carbonate (120 mg, 0.87 mmol) and N-cyclopentylguanidine hydrochloride (75 mg, 0.46 mmol) were added and the reaction heated for additional 3 hours. The reaction was allowed to cool and was stirred at room temperature for 16 hours. The mixture was quenched with water, extracted with ethyl acetate (2×), washed with brine, concentrated, and the residue purified by silica chromatography eluting with 5% acetone in dichloromethane to yield 140 mg (75%) of N-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-c]pyrimidin-7-amine. 1H NMR (CDCl3): δ 8.09 (d, 1H), 7.80 (d, 1H), 7.66 (dd, 2H), 7.54 (d, 1H), 7.19 (t, 2H), 6.42 (d, 1H), 6.30 (d, 1H), 5.14 (d, 1H), 4.57 (m, 1H), 4.34 (m, 1H), 2.22 (m, 2H), 2.09 (m, 2H), 1.52–1.89 (m, 12H).

Provenance & Evidence