Sodium Carbonate → 1-(3-Chloro-5-(2-(methylthio)pyrimidin-5-yl)pyridin-4-yl)piperidine-4-carboxamide

Participants

Reaction Steps

General procedure E was followed using 1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide (75 mg, 0.27 mmol), 2-(methylthio)pyrimidine-5-boronic acid (58 mg, 0.34 mmol), tetrakis(triphenylphosphine)palladium(0) (16 mg, 5 mol %), acetonitrile (3 mL) and 0.5 M sodium carbonate (0.77 mL, 0.38 mmol). The crude product was purified by flash column chromatography on silica gel (CH2Cl2, EtOH, 96:4-82:18, biotage 25+S) to furnish the title compound as an off white solid (11 mg, 11%), along with recovered 1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide as a white solid (41 mg, 55% RSM), LC-MS (ESI, 4 min) Rt 2.14 min, m/z 364 (100%, [M+H]+); m/z (ESI) C16H18N5OSCl requires 363.09206, found [M+H]+ 363.0922.

Provenance & Evidence