Acetone → 3',5'-DI-O-Mesylthymidine

Participants

Reaction Steps

To a dry, round-bottom flask purged with nitrogen was added thymidine (10.0 g, 0.0412 mole) and acetone (30 mL). The slurry was stirred and 3, 5-lutidine (17.7 g, 0.165 mole) was added. Then, methanesulfonyl chloride (13.8 g, 0.124 mole) was added over ten minutes with the temperature rising to 40° C. After 45 minutes, the reaction was complete and the thick slurry was diluted with 150 mL of water. The slurry was stirred for 25° C. for 30 minutes, and then cooled at 0°-5° C. for 30 minutes. The solids were collected, washed with water (80 mL) and isopropanol (40 mL), then dried to give 16.1 g (98.2%) of the title compound.

Provenance & Evidence