Imidazole → 7-(1-((Tert-butyldimethylsilyl)oxy)-2-methylpropan-2-YL)-2-chloro-5-iodo-7H-pyrrolo[2,3-D]pyrimidine

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Reaction Steps

t-Butyldimethylsilyl chloride (78.8 g, 518 mmol) was added to 2-(2-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-methylpropan-1-ol (140 g, 398 mmol) (see Preparation 43) and imidazole (67.8 g, 996 mmol) in DMF (996 mL) at 0° C. The mixture was stirred at room temperature for 16 hours. The mixture was poured into saturated aqueous sodium bicarbonate (1500 mL) and extracted with heptane:EtOAc (1:1, 1500 mL). The organic extract was washed with brine (2×900 mL) then dried over magnesium sulfate and evaporated in vacuo to afford the title compound as a brown gum in 96% yield, 178.2 g.

Provenance & Evidence