Isoamyl Alcohol → 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 2-(((3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol L-tartaric acid salt (17 g), sodium bicarbonate (21.2 g), 4,6-dichloro-2-(propylthio)pyrimidin-5-amine (10 g) and isoamyl alcohol (30 mL). The mixture was heated to about 100-110° C. and maintained at the same temperature for about 10-12 hours and completion of the reaction was monitored by TLC. After completion of reaction the mixture was cooled to room temperature then filtered and the bed was washed with isoamyl alcohol (10 mL). The filtrate was subjected to complete distillation under vacuum at about 65-70° C. to afford the crude. Then water (100 mL) and toluene (100 mL) were charged. The mixture was stirred for about 20 minutes and layers were separated. The organic layer was separated and washed with water (100 mL). The organic layer was separated and subjected to complete distillation under vacuum at 60-65° C. followed by cooling to room temperature and subsequent addition of n-heptane (150 mL). The mixture was stirred for about 4-5 hours followed by isolation of solid by filtration and washing with n-heptane (20 mL). The solid isolated was subjected to drying under vacuum at 50-55° C. to afford the title compound in about 82% yield having HPLC purity of about 99%.

Provenance & Evidence