The neighbouring pyrimidine group of the conjugate acid of 2-(4-aminopyrimidin-2-ylthio)-2-methyl-p-nitropropananilide (3) is an effective nucleophilic catalyst for the hydrolysis of the p-nitroanilide function. The reactivity of pyrimidine nitrogen parallels that of the carboxy group, and the mechanisms of the reactions with neighbouring amide functions are similar in detail.
I. B. Blagoeva and A. J. Kirby, J. Chem. Soc., Perkin Trans. 2, 1985, 1017 DOI: 10.1039/P29850001017
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