Sodium ethoxide → HCID 10172841, compound

Participants

Reaction Steps

To a mixture of cyclopentyl guanidine hydrochloride (1.05g, 6.43 mmol) in ethanol (60 mL) was added sodium ethoxide (2.15 mL, 3 M in ethanol, 6.43 mmol). The mixture was stirred at room temperature for 30 minutes then cooled to 0° C. A solution of 1-[2-(3-chlorophenyl)pyrazolo[1,5-c]pyrimidin-3-yl]-2-propyn-1-one (1.4 g, 4.97 mmol) in ethanol (100 mL) was added and the reaction mixture was stirred at room temperature 16 hours. The reaction mixture was diluted with water (200 mL) then concentrated to about two thirds the original volume. The precipitated solids were collected on a filter to provide 4-[2-(3-Chlorophenyl)pyrazolo[1,5-c]pyrimidin-3-yl]-N-cyclopentylpyrimidin-2-amine (1.25 g, 64%) as a white solid. Rf 0.19 (4:1 hexanes:ethyl acetate); 1H NMR (CDCl3) δ9.32 (s,1H), 8.22 (d,1H), 8.13 (d, 1H), 8.01 (d, 1H), 7.72 (s,1H), 7.55–7.39 (m, 3H), 6.38 (d,1H), 5.19 (d, 1H), 4.33 (m, 1H), 2.08 (m, 2H), 1.80–1.52 (m, 6H); MS m/z 391 (M+1).

Provenance & Evidence