5-Aminoimidazole-4-carboxamide hydrochloride → 4-(3,4-Dimethoxyphenyl)imidazo[1,5-a]pyrimidine-8-carboxamide

Participants

Reaction Steps

A stirred mixture of 15.0 g of 3-dimethylamino-3',4'-dimethoxyacrylophenone (prepared as described in Example 6) and 8.0 g of 4-amino-5-imidazolecarboxamide hydrochloride in 150 ml of glacial acetic acid was heated at reflux for 24 hours. The solvent was evaporated in vacuo to give an oil. The oil solidified on standing at room temperature. The solid was treated with 200 ml of saturated sodium bicarbonate solution and then filtered to collect the crystals. The material was treated by boiling with 700 ml of ethanol and then was filtered. The solid was recrystallized from methanol-chloroform to give 7.9 g of the desired product, mp 262°-265° C.

Provenance & Evidence