HCID 89616064, compound → HCID 89630067, compound

Participants

Reaction Steps

To a solution of N-(1-hydroxypropan-2-yl)-4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide (800 mg, 1.70 mmol) in dichloromethane (10 mL), was added DMP (1.20 g, 2.83 mmol). The resulting solution was stirred for 2 hours at room temperature and quenched by addition of saturated aqueous NaHCO3. The resulting solution was extracted with ethyl acetate (×3) and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The reaction was purified by chromatography using silica gel, eluting with 1-50% ethyl acetate/petroleum ether. The product was collected and concentrated in vacuo to afford 4-(3-nitrophenyl)-N-(1-oxopropan-2-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide as a yellow oil. LRMS (ESI) calc'd for C22H28N5O5Si [M+H]+: 470, found 470. 1H NMR (400 MHz, CDCl3) δ 9.53 (s, 1H), 9.12 (s, 1H), 9.09 (s, 1H), 8.57-7.68 (m, 5H), 5.80-5.78 (s, 2H), 4.54-4.51 (m, 1H), 3.66-3.62 (m, 2H), 1.36-1.27 (m, 3H), 1.02-0.98 (m, 2H), 0.02 (s, 9H).

Provenance & Evidence