Sodium hydride → HCID 21717278, compound

Participants

Reaction Steps

A solution of 5-acetyloxindole (352 mg, 2 mmol), (EP 0155828 A2), in DMF (5 ml) was added to a suspension of sodium hydride (80 mg, 2 mmol, prewashed with hexane) in DMF (1 ml) and the mixture stirred for 30 minutes at ambient temperature. 4-Chloro-6-methoxy-7-(2-methoxyethoxy)quinazoline (180 mg, 0.67 mmol), (prepared as described for the starting material in Example 2), was added and the mixture was heated at 50° C. for 1.5 hours. The mixture was partitioned between water and ether and the aqueous layer was adjusted to pH7 with 2M hydrochloric acid. The precipitate was collected by filtration, washed with water and dried under vacuum. The solid was dissolved in methylene chloride/methanol (30 ml/30 ml) and 7M ethanolic hydrogen chloride (1 ml) was added. The mixture was left to stand for 15 minutes at ambient temperature, the resulting precipitate was collected by filtration, washed with ether and dried under vacuum to give 4-(5-acetyloxindol-3-yl)-6-methoxy-7-(2-methoxyethoxy)quinazoline hydrochloride (195 mg, 71%).

Provenance & Evidence