Sodium hydride → HCID 9907179, compound

Participants

Reaction Steps

A solution of 7-azaoxindole (268 mg, 2 mmol) in THF (3 ml) was added to a suspension of sodium hydride (80 mg, 2 mmol, prewashed with THF) in THF (4 ml). After stirring for 20 minutes at ambient temperature a solution of 4-chloro-6-methoxy-7-(2-methoxyethoxy)quinazoline (180 mg, 0.7 mmol) in a mixture of THF (3 ml) and DMF (1 ml) was added. After stirring for 30 minutes at ambient temperature followed by 1 hour at 65° C., the volatiles were removed by evaporation. The residue was partitioned between water and ether. The aqueous layer was separated and adjusted to pH4 with 2M hydrochloric acid. The precipitate was collected by filtration and dried under vacuum, it was then suspended in methylene chloride/methanol (1/1) and 3M hydrogen chloride in ether was added. The solid was collected by filtration, washed with methanol followed by ether and dried under vacuum to give 4-(7-azaoxindol-3-yl)-6-methoxy-7-(2-methoxyethoxy)quinazoline (388 mg, 68%).

Provenance & Evidence