Dimethyl Sulfide → HCID 86600785, compound

Participants

Reaction Conditions

Reaction Steps

2-Amino-5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine (5.6 g, 0.029 mol) was slurried in dichloromethane (100 mL) and methyl sulfide (1.9 g, 0.031 mol) was added. The mixture was cooled to −25° C., and a solution of N-chlorosuccinimide (4.2 g, 0.031 mol) in acetonitrile (40 mL) was added to the reaction slurry over one hour, keeping the internal temperature at −22 to −28° C. When the addition was complete, the reaction was allowed to warm to room temperature over several hours. The new slurry was filtered and the solids washed with acetonitrile (2×40 mL). The solids were dried in a vacuum oven to provide 7.7 g of N-(5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)-S,S-dimethylsulfilimine hydrochloride as a light tan solid, m.p. 170-174° C. The material was 95 area % pure by HPLC, with the remainder being the amine starting material.

Provenance & Evidence