3,5-Dichlorobenzoyl chloride → 1-(3,5-dichlorobenzoyl)-5-fluoro-4-imino-3-methyl-3,4-dihydropyrimidin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

In a capped vial, (E)-trimethylsilyl-N-(trimethylsilyl)acetimidate (157 mg, 0.774) was added to 5-fluoro-4-imino-3-methyl-3,4-dihydropyrimidin-2(1H)-one (100 mg, 0.704 mmol) and acetonitrile (1.0 mL) and heated at 70° C. for 30 min. The solution was cooled to room temperature and 3,5-dichlorobenzoyl chloride (133 mg, 0.633 mmol) was added dropwise and the contents were stirred overnight at room temperature. The reaction was concentrated with a stream of nitrogen. Diethyl ether (Et2O; 3 mL) was added and the vial was recapped and shaken briefly. The solids were filtered and washed with a small amount of Et2O and air dried to provide the title compound as a white solid (78 mg, 35%): mp 142-143° C.; 1H NMR (400 MHz, CDCl3) δ 7.65 (d, J=5.5 Hz, 1H), 7.56 (t, J=1.8 Hz, 1H), 7.49 (d, J=1.8 Hz, 2H), 3.40 (s, 3H); 13C NMR (101 MHz, CDCl3) δ 166.97, 136.71, 135.23, 135.12, 132.76, 132.37, 127.95, 126.48, 114.66, 114.27, 29.56, 29.01; ESIMS m/z 317 ([M+H]+).

Provenance & Evidence