Sodium ethoxide → HCID 58765485, compound

Participants

Reaction Steps

To a suspension of N-cyclopentylguanidine hydrochloride (261 mg, 1.60 mmol) in ethanol (2 mL) was added sodium ethoxide (530 μL, 3 M in ethanol, 1.6 mmol). The mixture was stirred at room temperature for 10 minutes. To this suspension was added a mixture of (2E)-1-[7-chloro-2-(3-methylphenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-methyl-2-buten-1-one and (2Z)-1-[7-chloro-2-(3-methylphenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-methyl-2-buten-1-one (200 mg, 0.616 mmol) portionwise. The reaction mixture was stirred at 70° C. for 16 hours then cooled to room temperature. Palladium on carbon (10%, 230 mg) was added and the reaction mixture was stirred at 60° C. for 24 hours. The reaction mixture was diluted with ethanol (15 mL) and filtered through Celite. The filtrate was concentrated in vacuo and chromatographed (39:1 dichloromethane:methanol) to provide 4-[7-chloro-2-(3-methylphenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-5,6-dimethyl-2-pyrimidinamine (80 mg, 30%) as a light brown solid. Rf 0.47 (29:1 dichloromethane:methanol); 1H NMR (CDCl3) δ 7.60 (s, 1H), 7.55 (d, 1H), 7.32 (d, 1H), 7.21–7.11 (m, 3H), 6.96 (d, 1H), 4.99 (broad, 1H), 4.28 (m, 1H); 2.35 (s, 3H), 2.30 (s, 3H), 2.01 (m, 2H), 1.74–1.42 (9 H); MS m/z 432 (M+1).

Provenance & Evidence