Urea → 5-(2-chlorophenyl)pyrimidine-2,4(1H,3H)-dione

Participants

Reaction Steps

To a mixture of methyl 2-(2-chlorophenyl)-3-(dimethylamino)acrylate 2b (0.26 g, 1.08 mmol), urea (0.2 g, 3.26 mmol) and NaI (0.49 g, 3.26 mmol) in acetonitrile (5 mL) was added TMSCl (0.41 mL, 3.26 mmol). The resulting mixture was refluxed for 16 hours, cooled to room temperature, and 1.0 M NaOH (8 mL) was added. The resultant solution was stirred for 20 hr, and acetonitrile was removed in vacuo. The aq. solution was washed with ether, cooled in ice bath, and neutralized with 1 N HCl (8 mL). The precipitate was filtered, washed with additional H2O, and dried to give 5-(2-chlorophenyl)pyrimidine-2,4(1H,3H)-dione 2c (0.16 g, 66%) as a white solid. MS (CI) m/z 222.9, 224.9 (MH+).

Provenance & Evidence