Water → 5-Iodo-7-[[2-(trimethylsilyl)ethoxy]methyl]-7H-pyrrolo[2,3-d]pyrimidine

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Reaction Steps

To a stirred solution of 5-iodo-7H-pyrrolo[2,3-d]pyrimidine (Preparation 201, 735 mg, 3.00 mmol) in DMF (5 mL) at 0° C. was added to sodium hydride (132 mg, 3.30 mmol, 60% in oil). The mixture was stirred at room temperature for 30 minutes, cooled to −20° C. and 2-(trimethylsilyl)ethoxymethyl chloride (0.58 mL, 3.30 mmol) added. The reaction mixture was stirred at −20° C. for 3 hours then water (30 mL) was added. The mixture was extracted with EtOAc (2×50 mL) and the combined organic phases were dried over magnesium sulphate and evaporated under reduced pressure. The crude solid was purified by column chromatography on silica gel, eluting with a gradient of heptane:EtOAc 100:0 to 50:50), to afford the title compound as a white solid in 61% yield, 691 mg.

Provenance & Evidence