Sodium hydride → HCID 10299605, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 100 mg (0.236 mmol) of 1-(3-hydroxy-benzyl)-4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one in anhydrous DMF (5 ml) is added NaH (11 mg, 0.471 mmol) and the solution is allowed to stir until evolution of gas ceases. 1-Bromo-2-methoxy-ethane (34 μl, 0.236 mmol) is added and the mixture is heated for 2 days at 60° C. After cooling to room temperature, the reaction mixture is quenched with water and the mixture is acidified to pH 3 with 10% citric acid. The mixture is extracted with ether (2×20 ml). The combined organic layers are washed with brine, dried (Na2SO4), filtered and evaporated in vacuo to provide a yellow solid which is purified by flash chromatography on silica gel using petroleum ether/ethyl acetate (9:1 to 1:1) to provide the title compound as a yellow oil. Yield:56 mg (49%).

Provenance & Evidence