Cesium carbonate → HCID 10184334, compound

Participants

Reaction Steps

To a solution of 4-[3-[2-(cyclopentylamino)-4-pyrimidinyl]-7-(cyclopropylamino)pyrazolo[1,5-a]pyridin-2-yl]phenol (146 mg, 0.34 mmol) in N,N-dimethylformamide (3 mL) was added cesium carbonate (0.22 g, 0.68 mmol) and (bromomethyl)cyclopropane (66 μL, 0.68 mmol). The reaction was stirred for 1 hour at room temperature, then partitioned between water and ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (3:1 to 1:1 hexanes-ethyl acetate) provided 3-[2-(cyclopentylamino)-4-pyrimidinyl]-N-cyclopropyl-2-[4-(cyclopropylmethoxy)phenyl]pyrazolo[1,5-a]pyridin-7-amine (90.4 mg, 55%) as an off-white solid. 1H NMR (CDCl3): δ 7.99 (d, 1 H), 7.84 (d, 1 H), 7.55 (d, 2 H), 7.34 (t, 1 H), 6.98 (d, 2 H), 6.39–6.32 (m, 3 H), 5.08 (broad, 1 H), 4.37 (m, 1 H), 3.87 (d, 2 H), 2.68 (m, 1 H), 2.10 (m, 2 H), 1.80–1.27 (m, 6 H), 0.89 (m, 2 H), 0.78–0.65 (m, 4 H), 0.39 (m, 2 H); MS m/z 481 (M+1).

Provenance & Evidence