5-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione → HCID 51361338, compound

Participants

Reaction Steps

In a 10 mL round bottom flask was placed 4a (200 mg, 595 mmol) (see Example 2 for synthesis of 4a), 2-amino-4-chloro-5-nitrophenol (236 mg, 1.25 mmol), and ethanol (5 mL). The reaction was stirred at reflux for 5 h, then cooled and placed in a freezer. After several hours yellow crystals formed, which were filtered and rinsed with cold ethanol to give 5f (225 mg, 89%). 1H NMR (600 MHz, DMSO-d6) δ 11.33 (s, 1H), 7.79 (s, 1H), 7.44 (s, 1H), 7.30 (s, 5H), 7.10 (s, 1H), 3.33 (s, 3H), 3.20 (s, 3H). 13C NMR (151 MHz, DMSO-d6) δ 158.98, 152.39, 150.82, 147.31, 134.14, 131.79, 130.50, 130.32, 129.23, 128.96, 128.33, 127.48, 113.90, 112.93, 105.91, 102.66, 31.55, 27.51. MS (ES+) (m/z): [M+1]+ calculated for C20H16ClN4O5, 427.08. found 427.12.

Provenance & Evidence