Cesium carbonate → HCID 10114171, compound

Participants

Reaction Steps

To a solution of 4-[7-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (0.39 g, 0.93 mmol) in toluene (20 mL) was added successively racemic-BINAP (34.7 mg, 0.06 mmol), cesium carbonate (0.91 g, 2.8 mmol), cyclopropylamine (0.64 mL, 9.3 mmol) and palladium (II) acetate (8.3 mg, 0.04 mmol). The resultant mixture was heated under reflux for 8 hours. After cooling to room temperature the reaction mixture was partitioned between ether and water. The organic layer was washed with brine and dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (3:1 hexanes-ethyl acetate) provided 3-[2-(cyclopentylamino)-4-pyrimidinyl]-N-cyclopropyl-2-(4-methoxyphenyl)pyrazolo-[1,5-a]pyridin-7-amine (0.30 g, 73%) as a pale yellow solid. 1H NMR (CDCl3): δ 7.95 (d, 1 H), 7.85 (d, 1 H), 7.56 (d, 2 H), 7.36 (t, 1 H), 6.99 (d, 2 H), 6.40 (d, 1 H), 6.33 (m, 2 H), 4.38 (m, 1 H), 3.88 (s, 3 H), 2.68 (m, 1 H), 2.09 (m, 2H), 1.81–1.57 (m, 6 H), 0.89 (m, 2 H), 0.75 (m, 2 H); MS m/z 441 (M+1).

Provenance & Evidence