2,3-Dihydrofuran → HCID 89630016, compound

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of 5-bromo-4-(3-nitrophenyl)-7-[[2-(trimethylsilyl)ethoxy]methyl]-7H-pyrrolo[2,3-d]pyrimidine (1.30 g, 2.89 mmol) in N,N-dimethylformamide (40 mL), was added Pd(OAc)2 (650 mg, 2.90 mmol), Bu4NCl (1.00 g, 3.60 mmol), NaOAc (714 g, 8.71 mol) and 2,3-dihydrofuran (2.00 g, 28.5 mmol). The reaction was stirred for 2 hours at 50° C. and then quenched by the addition of water. The resulting solution was extracted with ethyl acetate (×3), and the organic layers were combined, washed with water, brine, then dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The reaction was purified by chromatography using silica gel, eluting with 1-50% EtOAc/petroleum ether. The product was collected and concentrated in vacuo to afford 5-(2,5-dihydrofuran-2-yl)-4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine as a yellow oil. LRMS (ESI) calc'd for C22H27N4O4Si [M+H]+: 439, found 439.

Provenance & Evidence