4-Toluenesulfonyl chloride → 4-Chloro-7-(p-toluenesulfonyl)-7H-pyrrolo[2,3-d]pyrimidine

Participants

Reaction Conditions

Reaction Steps

To a clean, dry, nitrogen-purged reactor were charged acetone (87.5 ml), p-toluenesulfonyl chloride (17.1 g, 0.09 mol) and 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (25.0 g, 0.16 mol). The reactor was cooled to between −5.0 to 5.0° C. and 2.5 M sodium hydroxide (78.1 ml) was added at a rate to maintain the temperature below 5.0° C. The reactor was warmed to between 20-30° C. and stirred for a minimum of 5 hours. The resulting solids were isolated by filtration and washed with acetone/water (1:1, 25 ml each). After drying for a minimum of 12 hours under vacuum at 40-50° C. with slight nitrogen bleed, 44.9 g (90.1%) of the title compound were isolated.

Provenance & Evidence