Intramolecular nucleophilic catalysis of anilide hydrolysis by pyrimidine nitrogen

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Abstract
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.
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