Benzenesulfonyl chloride → 4-Chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-D]pyrimidine

Participants

Reaction Conditions

Reaction Steps

In a flame-dried flask under nitrogen, 780 mg of 60% sodium hydride (19.5 mmol) in mineral oil was added to 30 mL of dimethylformamide (DMF) and the resulting mixture cooled to 0° C. A solution of 2.0 g (13.0 mmol) of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine in 10 mL of DMF was added slowly over a 5 minute period. The reaction was stirred for 10 min at which time generation of hydrogen (H2) ceased. Benzenesulfonylchloride (1.7 mL/13.0 mmol) was added, the reaction warmed to room temperature and stirred for 1 hour. Water was added, and the resulting precipitate was filtered and dried in vacuo to obtain 3.4 grams (89%) of the title compound as a crystalline solid, mp 163-167° C.

Provenance & Evidence