1,1'-Thiocarbonyldiimidazole → HCID 19864373, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 1.0 g of 1,2-dihydro-4-phenylimidazo[1,5-a]pyrimidine-8-carboxamide (prepared as described in Example 29) in 30 ml of dry tetrahydrofuran cooled to -78° C. in a dry ice acetone bath was added in one portion 360 mg of sodium hydride (60% dispersion in mineral oil). The reaction mixture was stirred at -78° C. for 30 minutes then 817 mg of 1,1'-thiocarbonyldiimidazole was added in one portion and the mixture was stirred at -78° C. for 3 hours then allowed to warm slowly to room temperature and was stirred at room temperature for 36 hours. The reaction mixture was quenched with water and neutralized with 5% hydrochloric acid. The aqueous solution was extracted with chloroform. The organic layer was separated and evaporated in vacuo to give the product of the example as a yellow solid, mp 316°-317° C. (dec.).

Provenance & Evidence