Sodium Hydroxide → N-(3-(1H-imidazol-1-yl)phenyl)-4-(2-pyridinyl)-2-pyrimidinamine

Participants

Reaction Steps

Thirteen and seven tenths grams of [3-(1H-imidazol-1-yl)phenyl]guanidine, dihydrochloride (2) from Example 1, 8.8 g of 3-dimethylamino-1-(2-pyridyl)-2-propen-1-one (3), 50 ml of n-propanol and 10 ml of 10N sodium hydroxide is refluxed for 18 hours. The reaction is diluted with 50 ml of n-propanol and filtered. The collected yellow solid is stirred in 300 ml of water for 0.5 hour, filtered and washed with 50 ml of n-propanol followed by 100 ml of diethyl ether. The solid is air dried overnight giving 13.4 g (85%) of the desired product, mp 210°-211° C. The overall yield following this procedure is 73%.

Provenance & Evidence