Sodium hydride → HCID 19864378, compound

Participants

Reaction Steps

To a stirred suspension of 5.0 g of 4-[3-(trifluoromethyl)phenyl]-6H,8H-pyrimido[1,2,3-cd]purine-8,10-(9H)-dione (prepared as described in Example 41) in 50 ml of dry N,N-dimethylformamide at room temperature, under nitrogen, was added 800 mg of sodium hydride (60% dispersion in mineral oil). The mixture was stirred for 2 hours, then 3.3 g of p-nitrobenzyl bromide in 10 ml of N,N-dimethylformamide was added and the mixture was stirred at room temperature for 40 hours. The mixture was evaporated to dryness, then was treated with water. The solid formed was collected by filtration, washed with water and dried in vacuo. The solid was stirred with 200 ml of dichloromethane and filtered. The filtrate was passed through a short column of magnesium silicate and the eluate was evaporated in vacuo to give 4.34 g of the product of the example which was recrystallized from isopropyl alcohol/acetonitrile as a white solid, mp 230°-232° C.

Provenance & Evidence