2-Propen-1-one, 3-(dimethylamino)-1-(4-pyridinyl)- → 2-Methyl-7-(4-pyridinyl)pyrazolo(1,5-a) pyrimidine-3-carbonitrile

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Reaction Steps

A mixture of 6.1 g of 5-amino-3-methyl-4-pyrazole carbonitrile and 8.81 g of 3-dimethylamino-1-(4-pyridinyl)-2-propen-1-one in 50 ml of glacial acetic acid is stirred and heated at reflux for 5 hours. The reaction mixture is cooled and the precipitate which forms is collected by filtration and washed with water and a little dichloromethane to give a solid. The solid is partitioned between saturated sodium bicarbonate and dichloromethane. The organic layer is dried over anhydrous sodium sulfate and passed through a short column of hydrous magensium silicate. The addition of hexane to the eluate crystallizes the product which is collected by filtration to give 6.17 g of the desired product, mp 220°-221° C.

Provenance & Evidence