Sodium ethoxide → HCID 57444748, compound

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Reaction Steps

To a mixture of 1-[7-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-one (1.57 g, 5.0 mmol) and N-cyclopentylguanidine hydrochloride (1.07 g, 6.6 mmol) in ethanol (50 mL) was added sodium ethoxide (2.5 mL, 21 wt % in ethanol, 6.6 mmol). The resulting suspension was stirred overnight at room temperature, then diluted with water and extracted with ethyl acetate. The organic extracts were washed with brine and dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (7:3 to 3:2 hexanes-ethyl acetate) provided 4-[7-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (1.77 g, 83%) as a pale yellow solid. 1H NMR (CDCl3): δ 8.44 (d, 1 H), 8.05 (d, 1 H), 7.60 (d, 2 H), 7.28 (m, 1 H), 7.06–6.96 (m, 3 H), 6.38 (d, 1 H), 5.31 (broad, 1 H), 4.38 (m, 1 H), 3.88 (s, 3 H), 2.12 (m, 2 H), 1.84–1.53 (m, 6 H); MS m/z 420 (M+1).

Provenance & Evidence