Methacryloyl chloride → HCID 131732646, compound

Participants

Reaction Steps

To a 0° C. solution of crude 3-(5-(tetrahydrofuran-2-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)aniline (410 mg, 1.00 mmol) in THF (10 mL), was added DIPEA (258 mg, 2.00 mmol) followed by dropwise addition of 2-methylprop-2-enoyl chloride (125 mg, 1.20 mmol). The resulting solution was stirred for 4 hours at room temperature prior to being quenched by addition of water. 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 0-100% EtOAc/petroleum ether. The product was collected and concentrated in vacuo to afford N-(3-(5-(tetrahydrofuran-2-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)phenyl)methacrylamide as a off-white solid. LRMS (ESI) calc'd for C26H35N4O3Si [M+H]+: 479, found 479.

Provenance & Evidence