Dimethylformamide → HCID 21948537, compound

Participants

Reaction Steps

A solution of 4-(4-Iodo-1H-pyrazol-5-yl)-2-(methylthio)pyrimidine (4-2, 710 mg, 2.23 mmol, 1 equiv), zinc cyanide(157 mg, 1.34 mmol, 0.6 equiv), 1,1′-bis(diphenylphosphino)ferrocene (297 mg, 0.54 mmol, 0.24 equiv), and tris (dibenzylideneacetone)dipalladium(0) (204 mg, 0.22 mmol, 0.1 equiv) in DMF (10 mL) was degassed and placed in a 105° C. oil bath. After 1 hour the reaction was concentrated and partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic layer was washed with brine, dried over magnesium sulfate and concentrated. The resulting oil was purified by chromatographed. Elution with 5–25% EtOAc/CH2Cl2 gave 4-(4-cyano-1H-pyrazol-5-yl)-2-(methylthio)pyrimidine (4-3) as a tan solid. LRMS m/z: Calc'd for C9H7N5S (M+H) 318.1. found 318.0.

Provenance & Evidence