Sodium hydride → tert-butyl trans-3-{[(2-chloro-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy]methyl}-4-methylpyrrolidine-1-carboxylate

Participants

Reaction Steps

To a stirred solution of tert-butyl trans-3-(hydroxymethyl)-4-methylpyrrolidine-1-carboxylate (0.58 g, 2.7 mmol) in DMF (15 mL) was added NaH (60% in oil, 162 mg, 4.05 mmol) at 0° C. After stirring at rt for 30 min, 2,4-dichloro-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (0.85 g, 2.7 mmol) was added to the mixture. The resulting mixture was stirred at rt for 1 hr. TLC (petroleum ether/EtOAc=5:1) showed the reaction was complete. The reaction mixture was quenched by water (10 mL) and extracted with EtOAc (two×20 mL). The combined organic layers were washed with brine (four×20 mL), dried over Na2SO4 and concentrated to yield the title compound (1.34 g, 100% yield) as a brown oil.

Provenance & Evidence