Investigation of the Nucleophilic Rearrangement of 2-(Cyanomethyl)-1,4,6-trimethylpyrimidinium Iodide Into 4,6-Dimethyl-2-methylaminonicotinic Acid Nitrile

2-(Cyanomethyl)-1,4,6-trimethylpyrimidinium iodide is rearranged into 4,6-dimethyl-2-methylaminonicotinic acid nitrile by interaction with alcoholic solutions of sodium ethylate, methylamine, and also glycine and -alanine ethyl esters. This conversion was also observed for the first time for pyrimidinium salts during the process of recording ¹H NMR spectra in CD₃OD solution containing CD₃ONa. After the rearrangement deuterium exchange of the protons of the pyridine ring methyl groups was noted spectrally. It was demonstrated experimentally that for carrying out and completing the recyclization a quantity of nucleophilic reagent must convert the molar equivalent quantity of pyridinium salt.