Ammonia → 6-aminocarbonyl-4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidine

Participants

Reaction Conditions

Reaction Steps

Alternative stage 10.1: A mixture of 2.165 g (7.5 mmol) of 6-carboxy-4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidine in 60 ml of THF and 10 ml of DMPU is heated under reflux for 30 min and then cooled to 0° C., whereupon a fine suspension is obtained. 824 μl (7.5 mmol) of N-methylmorpholine followed by 981 μl (7.5 mmol of isobutyl chloroformate in 10 ml of THF and, after 1 h at 0° C., 824 μl (7.5 mmol) of N-methylmorpholine followed by 981 μl (7.5 mmol) of isobutyl chloroformate again are added dropwise. The mixture is stirred for 1 h and then added dropwise to 70 ml of a saturated solution of ammonia in dioxane. After 3 h, the mixture is concentrated in vacuo. The residue is poured into water, and the precipitate is filtered off and washed with water and boiling isopropanol, whereupon 6-aminocarbonyl-4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidine is obtained. Further product is obtained from the isopropanol filtrate.

Provenance & Evidence