Studies on the Azaindolizine Compounds. XII. Alkyl Rearrangement of 5-Methyl-7-alkoxy-s-triazolo [1, 5-a] pyrimidines.

5-Methyl-7-methoxy-s-triazolo [1, 5-a] pyrimidine (IVa) was prepared by the reaction of the 7-chloro compound III with sodium methoxide at below room temperature. The property of the 7-alkoxy derivatives (IVa and IVb) was examined and it was discovered that the alkyl group of these derivatives undergoes rearrangement to the ring nitrogen at 3- and 4-positions. In order to determine the structure of the products being obtained by above rearrangement, the reaction of ethyl acetoacetate with 5-alkylaminos-triazoles (XIVa and XIVb) and 4-alkyl-5-aminos-triazoles (XVa and XVb) which were prepared from 1-alkyl-2-aminoguanidinium sulfates (XIIa and XIIb), was investigated.