Dimethyl Sulfoxide → 2-(((3aR,4S,6R,6aS)-6-((5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl)amino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol

Participants

Reaction Conditions

Reaction Steps

A flask was charged with 4,6-dichloro-2-(propylthio)pyrimidin-5-amine (3 g), 2-(((3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol L-tartaric acid salt (5.1 g), dimethyl sulfoxide (30 mL) and sodium bicarbonate (6.3 g). The mixture was heated to about 60-65° C. and maintained at the same temperature for about 10 hours and completion of the reaction was monitored by TLC. After completion of reaction the mixture was cooled to 25-30° C. followed by addition of water (30 mL) and toluene (30 mL). The mixture was stirred for about 10 minutes and layers were separated. The organic layer was with water (30 mL). The organic layer was separated and subjected to complete distillation under vacuum at 55-60° C. followed by cooling to room temperature and subsequent addition of n-hexane (45 mL). The mixture was stirred for about 3 hours at room temperature followed by isolation of solid by filtration and washing with n-hexane (15 mL). The solid isolated was subjected to drying under vacuum at 55-60° C. for about 4 hours to afford the title compound in about 78% yield having HPLC purity of about 98%.

Provenance & Evidence