Reaction of 2,4,6-trialkylpyrimidine 1,3-dioxides with electrophilic reagents

Article abstract of DOI:10.1007/BF00507100

The nitrosation of 2,4,6-trimethylpyrimidine 1,3-dioxide and the bromination of 2,4,6-trimethyl- and 2-ethyl-4,6-dimethylpyrimidine 1,3-dioxides take place primarily at the methyl groups in the 4 and 6 positions of the heteroring. In the reaction of 2,4,6-trimethylpyrimidine 1,3-dioxide with phosphorus oxychloride chlorine is incorporated in the methyl group in the 2 position of the heteroring, while in the reaction with acetic anhydride an acetoxy group is incorporated in the methyl group in the 2 position and in the 5 position of the heteroring, whereas in the case of tosyl chloride a tosyloxy group is incorporated in the 5 position of the heteroring.