HCID 85865902, compound → HCID 86598491, compound

Participants

Reaction Steps

To a solution of 2-(3-chlorophenyl)pyrazolo[1,5-c]pyrimidine-3-carbaldehyde (1.5 g, 5.82 mmol) in tetrahydrofuran (50 mL) was added ethynylmagnesium bromide (17 mL, 0.5 M in tetrahydrofuran, 8.73 mmol). The reaction mixture was stirred 4 hours at room temperature then quenched with water. The mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, then dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (2:1 hexanes:ethyl acetate) provided 1-[2-(3-chlorophenyl)pyrazolo[1.5-c]pyrimidin-3-yl]-2-propyn-1-ol (1.41 g, 85%). Rf 0.17 (2:1 hexanes:ethyl acetate); 1H NMR (CDCl3) δ 9.27 (s, 1H), 7.93–7.90 (m, 2H), 7.83 (s, 1H), 7.73 (d, 1H), 7.50–7.41 (m, 2H), 5.78 (s, 1H), 2.99 (br, 1H), 2.71 (s, 1H); MS m/z 284 (M+1).

Provenance & Evidence