| Abstract: | 4(3H)-Pyrimidinone, as well as its 5-acetoxy and 5-methoxy derivatives, undergoes selective acetylation at N-1 when treated with acetic anhydride. In the presence of water, these 1-acetylpyrimidines undergo spontaneous covalent hydration at C-2 and cleavage of the 1,2-bond to give crystalline cis-3-acetylamino-N-formyl-acrylamides, generally in good yield. In contrast, the 6-methyl derivative of 4(3H)-pyrimidinone forms an equilibrium mixture of acetylated products that undergo the ring opening process to only a very limited extent, the major product (11%) being the 3-formylamino-N-acetylacrylamide derivative formed via N-3 acetylation and cleavage of the 2,3-bond. |
