Sodium hydride → 4-(5-Benzylpyrazol-3-yloxy)-6-methoxy-7-(3-morpholinopropoxy)quinazoline

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Reaction Steps

3-Benzyl-4,5-dihydro-1H-pyrazol-5-one (174 mg, 1 mmol), (J. Chem. Soc. Perk. Trans 1, 1980, 1618-1621), was added to a suspension of sodium hydride (40 mg, 1 mmol, prewashed with pentane) in DMF (3 ml) under nitrogen. After stirring for 30 minutes at ambient temperature, 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (135 mg, 0.4 mmol) was added and the mixture was heated at 80° C for 1 hour. After cooling, the mixture was diluted with saturated aqueous ammonium chloride solution and partitioned between ethyl acetate and water. The precipitate was collected by filtration, washed with water, followed by ethanol, ether and dried under vacuum to give 4-(5-benzylpyrazol-3-yloxy)-6-methoxy-7-(3-morpholinopropoxy)quinazoline (150 mg, 79%).

Provenance & Evidence