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

Participants

Reaction Steps

In a 1 l three-necked flask, introduce, with stirring, 11.8 g of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine and 137 ml of toluene, then 16.11 g of 4-methyl-benzenesulphonyl chloride and 5.2 g of tetra-n-butylammonium hydrogen sulphate, then run in, dropwise, 275 ml of an aqueous solution containing 30.7 g of sodium hydroxide. After 30 minutes at room temperature, add 200 ml of ethyl acetate and 200 ml of water. The organic phase is decanted, dried over magnesium sulphate, and concentrated under reduced pressure. After purification by flash chromatography on silica gel, eluting with dichloromethane, we obtain 22.6 g of 4-chloro-7-(4-methylbenzenesulphonyl)-7H-pyrrolo[2,3-d]pyrimidine, in the form of a white solid with the following characteristics:

Provenance & Evidence