Acetic Acid → Methyl (6-methyl-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-2-yl)carbamate

Participants

Reaction Steps

The pyrrole 6 (2.68 g, 16 mmol) was dissolved in MeOH (40 mL), and 1,3-bis(methoxycarbonyl)-2-methyl-2-thiopseudourea (3.74 g, 18 mmol) was added followed by AcOH (4.6 mL). The mixture was stirred at room temperature overnight and became a thick paste. To the reaction mixture NaOMe in MeOH (25%) 45 mL was added, and stirring was continued at room temperature for 2 h. The mixture was neutralized with AcOH and the solid collected by filtration and washed well with water. After drying, 7 (2.44 g, 69%) was obtained as an off-white powder: mp 234-236° C.; TLC Rf0.22 (MeOH/CHCl3, 1:5); 1H NMR (DMSO-d6) δ 2.28 (s, 3 H, CH3), 3.73 (s, 3 H, OCH3), 5.95 (s, 1 H), 10.90 (s, 1 H), 11.10 (s, 1 H), 11.76 (1 H). Anal. (C9H10N4O3.0.79C6H6.0.55C7H8O3S) C, H, N.

Provenance & Evidence