Imidazole → HCID 89630146, compound

Participants

Reaction Steps

To a solution of N′-acetyl-4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbohydrazide (470 mg, 1.00 mmol) in dichloromethane (10 mL) was added imidazole (0.15 g, 2.2 mmol), CBr4 (0.72 g, 2.2 mmol) and PPh3 (0.58 g, 2.2 mmol). The reaction was stirred for 1 hour at room temperature and then concentrated in vacuo. The reaction was purified by chromatography using silica gel, eluting with 1-20% ethyl acetate/petroleum ether. The product was collected and concentrated in vacuo to afford 2-methyl-5-(4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-1,3,4-oxadiazole as a white solid. 1NMR (300 MHz, CD3OD) δ 9.08 (s, 1H), 8.45-8.34 (m, 3H), 8.01-7.98 (m, 1H), 7.74-7.53 (m, 1H), 5.87 (s, 2H), 3.74-3.69 (m, 2H), 2.29 (s, 3H), 0.98-0.93 (m, 2H), 0.02 (s, 9H).

Provenance & Evidence