Dimethylformamide → 3-(3-thienyl)-6-(4-hydroxyphenyl)-pyrazolo(1,5-A)pyrimidine

Participants

Reaction Conditions

Reaction Steps

Ethanethiol (30 mg, 36 uL) was added dropwise over 1 min to a suspension of sodium hydride (23 mg, 0.98 mmol) in 10 dry DMF (2 mL) under argon. After 15 min, the compound of example 2 (50 mg, 0.16 mmol) was added and the reaction mixture was heated at 150° C. for 1.5 h. The resulting brown solution was cooled, poured into water (25 mL) and washed with ethyl acetate (2×25 mL). The combined organics were dried (Na2SO4), is concentrated, and purified by flash chromatography (40% EtOAc/Hexanes) to give the title compound as a yellow solid [11 mg, 23%, Rf=0.12 (40% EtOAc/Hexanes)]: 1H NMR (CD3OD) δ8.96 (d, 1H, J=2.4Hz), 8.85 (d, 1H, J=2.2Hz), 8.44 (s, 1H), 7.94 (dd, 1H, J=2.9, 1.2Hz), 7.74 (dd, 1H, J=4.9, 1.2Hz), 7.56 (d, 2 H, J=8.8Hz), 7.46 (dd, 1H, J=4.9, 2.9Hz), 6.94 (d, 2H,J=8.6Hz).

Provenance & Evidence