Selective hydrolysis of 2,4-diaminopyrimidine systems: A theoretical and experimental insight into an old rule

J. Teixidó, J. I. Borrell, C. Colominas, X. Deupí, J. L. Matallana, J. L. Falcó, B. Martinez-Teipel

Research output: Indexed journal article Articlepeer-review

8 Citations (Scopus)

Abstract

Hydrolysis of the amino groups in condensed 2,4-diaminopyrimidine systems (1) has been used as a common method for the synthesis of oxo-substituted pyrimidines. In particular, the treatment with 6 M HCl usually yields exclusively the 2-amino-4-oxopyrimidine isomer (2). During our work we found that the hydrolysis of the amino groups present in some condensed 2,4-diaminopyrimidine systems unexpectedly afforded exclusively the 4-amino-2-oxopyrimidine isomer (3). In this paper, we present the experimental work and ab initio calculations carried out to understand this discrepancy. As a part of such study, eight compounds containing a 2,4-diaminopyrimidine moiety were calculated in gas phase and in aqueous solution, and some acid hydrolyses were reexamined. Results showed that the presence, of an electron-donating nitrogen linked to C6 of the 2,4-diaminopyrimidine ring changes the preferred hydrolysis site to yield the 4-amino-2-oxopyrimidine isomer.

Original languageEnglish
Pages (from-to)192-199
Number of pages8
JournalJournal of Organic Chemistry
Volume66
Issue number1
DOIs
Publication statusPublished - 12 Jan 2001

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