Carbon Disulfide → HCID 18985861, compound

Participants

Reaction Steps

4-Hydrazino-2-methylthiopyrido[3,2-d]pyrimidine (14.5 g, 70 mmol) was combined with 200 mL of dioxane, 12.6 mL (16.0 g, 210 mmol) of carbon disulfide, and 29 mL (21.2 g, 210 mmol) of triethylamine and the mixture was heated at reflux with stirring for 4 hours during which time another 50 mL of dioxane was added to facilitate stirring. The mixture was allowed to cool, 13.3 g (105 mmol) of benzyl chloride was added, and the resulting mixture was allowed to stir overnight. Another 6 g of benzyl chloride and 25 mL of triethylamine were added and the mixture was heated to reflux with stirring for a short period. The volatile components were removed by evaporation under reduced pressure and the residue was diluted with dichloromethane and water. The resultant emulsion was filtered to obtain separable phases and the organic phase was washed with water, dried over magnesium sulfate, and concentrated by evaporation under reduced pressure. The residue was diluted with hexane and the resulting black solid was recovered by filtration. This solid was diluted with dichloromethane and the solution obtained was filtered through silica gel. Evaporation of the filtrate under reduced pressure gave a black solid that was diluted with ether and recovered by filtration to obtain 18.8 g the title compound melting at 157°-158° C. The proton NMR spectrum was compatible with the assigned structure. Work up of the filtrate gave an additional 6 g of impure title compound as a black oil.

Provenance & Evidence