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 triethyl amine (7.05 g). The mixture was heated to about 60-65° C. and maintained at the same temperature for about 24 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 sequentially washed with 5% aqueous sodium carbonate solution (30 mL), 5% aqueous acetic acid solution (30 mL) and sodium chloride solution (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 (55 mL). The mixture was stirred for about 2-3 hours followed by isolation of solid by filtration and washing with n-hexane (10 mL). The solid isolated was subjected to drying under vacuum at 55-60° C. for 90 minutes to afford the title compound in about 60% yield having HPLC purity of about 96%.

Provenance & Evidence