Benzenesulfonyl chloride → HCID 57818855, compound

Participants

Reaction Steps

N-(5-Fluoro-2-hydroxypyrimidin-4-yl)-acetamide* (200 mg, 1.17 mmol) was suspended in pyridine (5 mL) and stirred at ambient temperature. To the stirred suspension was added benzenesulfonyl chloride (226 mg, 1.29 mmol) and agitation was continued for 16 hours. The solvent was evaporated under a stream of nitrogen and the residue was suspended in dichloromethane (2-3 mL), placed directly onto a silica gel column, and eluted with ethyl acetate in petroleum ether (0-50% gradient) to isolate 180 mg, 0.58 mmol (49%) of the title compound as a white solid: mp 142-143° C.; 1H NMR (DMSO-d6) δ 10.96 (s, 1H), 8.67 (d, J=2.6 Hz, 1H), 8.12-8.06 (m, 2H), 7.86-7.79 (m, 1H), 7.73-7.65 (m, 2H), 2.98 (s, 3H); HPLC-MS (ESI) m/z 312 (M+H)+, 310 (M−H)−. *N-(5-Fluoro-2-hydroxypyrimidin-4-yl)-acetamide can be prepared through known literature methods. 1. Duschinsky, R., Fells, E., Hoffer, M. U.S. Pat. No. 3,309,359

Provenance & Evidence