HCID 89630016, compound → HCID 89630030, compound

Participants

Reaction Steps

To a solution of 5-(2,5-dihydrofuran-2-yl)-4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (500 mg, 1.14 mmol) in methanol (6.0 mL), was added Pd/C (250 mg, 10 wt. % loading Pd). The atmosphere was purged with hydrogen gas and the resulting solution was stirred for 12 hours at room temperature under hydrogen atmosphere (1 atm). The reaction was then filtered and concentrated in vacuo to afford crude 3-(5-(tetrahydrofuran-2-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)aniline as a yellow oil. LRMS (ESI) calc'd for C22H31N4O2Si [M+H]+: 411, found 411. 1H NMR (400 MHz, CD3OD) δ 8.79 (d, J 3.2 Hz, 1H), 7.59 (s, 1H), 7.35-7.26 (m, 1H), 6.88-6.98 (m, 3H), 5.71 (s, 2H), 5.07-5.01 (m, 1H), 3.99-3.97 (m, 1H), 3.75-3.72 (m, 1H), 3.63-3.59 (m, 2H), 1.80-1.73 (m, 2H), 1.58-1.53 (m, 1H), 1.41-1.30 (m, 1H), 0.92-0.88 (m, 2H), 0.02 (s, 9H).

Provenance & Evidence