Methyl chloroformate → 6-Amino-9-(phenylmethyl)-9H-purin-8-yl methyl carbonate

Participants

Reaction Steps

241 mg (1 mmol) of 9-benzyl-8-hydroxyadenine was dissolved in 20 ml of anhydrous THF. To this solution, 202 mg (2 mmol) of triethylamine and 111 mg (0.5 mmol) of dimethylaminopyridine were added and stirred for 1 hr at room temperature. To the resultant mixture, 113 mg (1.2 mmol) of methyl chloroformate was added and stirred overnight at room temperature. 50 ml each of ethyl acetate and water were added thereto for extraction. After the organic layer was removed by vacuum distillation, 20 ml of ether was added to the residue. Then, crystals were collected by filtration (300 mg; yield: 100%).

Provenance & Evidence