Ethyl chloroformate → Ethyl-4-chloro-5-(4-(ethoxycarbonyloxy)but-1-ynyl)-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7h-pyrrolo[2,3-d]pyrimidin-2-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

A suspension of 4-[2-Amino-4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-but-3-yn-1-ol (see example 2) (0.73 g) in anhydrous pyridine (5 mL) and DCM (25 mL) was treated with ethyl chloroformate (1 mL) at rt for 30 min. The mixture was cooled to 0° C., treated with addition EtOCOCl (1 mL), and the temperature was allowed to slowly reach rt overnight. The reaction mixture was diluted with DCM (30 mL) and washed sequentially with H2O, NH4OH 1M, and brine. The DCM was evaporated, but not the residual pyridine, Addition of MeOH (20 mL) induced crystallization of the product, as white needles. HPLC Rt=6.28 min.

Provenance & Evidence