Propylphosphonic anhydride → Ethyl 4-(3-{[2-({[tert-butyl(dimethyl)silyl]oxy}methyl)acryloyl]amino}phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

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Reaction Conditions

Reaction Steps

To ethyl 4-(3-aminophenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (80 mg, 0.28 mmol) was added tetrahydrofuran (2.8 mL), TEA (59.2 μL, 0.425 mmol), 2-({[tert-butyl(dimethyl)silyl]oxy}methyl)prop-2-enoic acid (80 mg, 0.37 mmol) and 1-propanephosphonic acid cyclic anhydride (169 μL, 0.283 mmol). The reaction was stirred at 25° C. overnight before being quenched by pouring into a separatory funnel containing aqueous sodium bicarbonate (5%). The solution was extracted with ethyl acetate (×3) and the organic layers were combined and dried with Na2SO4, filtered, and concentrated in vacuo. The crude product was then purified by silica chromatography by MPLC using 1-8% CH2Cl2MeOH. Concentration of the desired fractions afforded the title compound as a colorless solid. LRMS (ESI) calc'd for C25H33N4O4Si [M+H]+, 481; found 481.

Provenance & Evidence