Ethyl Acetate → HCID 10279403, compound

Participants

Reaction Steps

To a solution of 4-[5-chloro-3-[2-(cyclopentylamino)-4-pyrimidinyl]-7-(cyclopropylamino)pyrazolo[1,5-a]pyridin-2-yl]phenol (110 mg, 0.24 mmol) in acetonitrile was added bromomethyl cyclopropane (96 mg, 0.72 mmol) and cesium carbonate (85 mg, 0.26 mmol). The reaction mixture was heated at reflux for 6 hours. After cooling to room temperature, ethyl acetate was added to the reaction mixture. The organic phase was washed with water and brine, then dried over magnesium sulfate. Filtration and concentration, followed by flash chromatography (2:5 hexanes/ethyl acetate), gave 5-chloro-3-[2-(cyclopentylamino)-4-pyrimidinyl]-N-cyclopropyl-2-[4-(cyclopropylmethoxy)phenyl]pyrazolo[1,5-a]pyridin-7-amine (75 mg, 61%) as a yellow solid. 1H NMR (CDCl3) δ 7.97 (d, 1H), 7.90 (s, 1H), 7.50 (d, 2H), 6.95 (d, 2H), 6.38 (s, 1H), 6.32 (d, 1H), 6.28 (d, 1H), 5.13 (d, 1H), 4.36 (m, 1H), 3.85 (d, 2H), 2.64 (m, 1H), 2.10 (m, 2H), 1.80–1.66 (m, 4H), 1.55 (m, 2H), 1.30 (m, 1H), 0.88 (m, 2H), 0.74 (m, 2H), 0.66 (m, 2H), 0.39 (m, 2H). MS m/z 515 (M+1).

Provenance & Evidence