5-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione → 6-(2-hydroxy-5-nitrophenyl)-1,3-dimethyl-5-phenyl-1Hpyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Participants

Reaction Steps

In a 25 mL round bottom flask was placed 4a (1.00 g, 2.97 mmol) (see Example 2 for synthesis of 4a), 2-amino-4-nitrophenol (921 mg, 5.98 mmol), and methanol (12 mL). The reaction was stirred at reflux for 5 h, then cooled in an ice bath. The precipitate was filtered and rinsed with cold methanol to give 5g (1.32 g, 94%). 1H NMR (600 MHz, DMSO-d6) δ 11.72 (s, 1H), 8.19 (d, J=2.8, 1H), 8.15 (dd, J=2.9, 9.1, 1H), 7.31-7.21 (m, 5H), 7.08 (s, 1H), 7.01 (d, J=9.1, 1H), 3.34 (s, 3H), 3.21 (s, 3H). 13C NMR (151 MHz, DMSO-d6) δ 159.26, 159.03, 150.85, 138.89, 134.18, 130.34, 129.34, 128.85, 128.14, 127.36, 126.15, 126.09, 125.45, 116.60, 105.95, 102.41, 31.52, 27.48. MS (ES+) (m/z): [M+1]+ calculated for C20H17N4O5, 393.12. found 393.02.

Provenance & Evidence