Sodium hydride → HCID 15702769, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 63.0 g of 7-(3-fluorophenyl)-4,5-dihydropyrazolo(1,5-a)pyrimidine-3-carboxamide (Example 11) and 2.5 liters of dry tetrahydrofuran is stirred and cooled to -78° C. in a dry ice-acetone bath, then 18.0 g of sodium hydride (60 percent dispersion in mineral oil) is added in one portion This mixture is stirred at -78° C. for 1.5 hours then 40.0 g of 1,1'-thiocarbonyldiimidazole is added and stirring is continued at -78° C. for 2 hours. The mixture is allowed to warm to room temperature and is stirred for 48 hours and then the reaction is quenched with 2.5 liters of water and neutralized with 5 percent aqueous hydrochloric acid. The crystalline solid that forms is collected, washed with ether and dried to give 54.6 g of the desired product as cream colored crystals, mp 298-300° C.

Provenance & Evidence