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Synlett 2012(4): 632-636  
DOI: 10.1055/s-0031-1290347
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Ugi-Smiles Coupling of Thiouracil Derivatives towards 2,4-Diamino Pyrimidines

Madjid Ait Sidhoum, Laurent El Kaïm*, Laurence Grimaud*
Laboratoire DCSO ENSTA-Polytechnique-CNRS, UMR 7652, Ecole Nationale Supérieure de Techniques Avancées, 32 Bd Victor, 75739 Paris, Cedex 15, France
Fax: +33(1)45528322; e-Mail: laurent.elkaim@ensta.fr; e-Mail: grimaud@dcso.polytechnique.fr;
Further Information

Publication History

Received 4 November 2011
Publication Date:
10 February 2012 (online)

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Abstract

Diaminopyrimidines could be synthesized via a multicomponent coupling starting from S-alkyl thiouracil derivatives. The synthetic strategy based upon an Ugi-Smiles coupling, and subsequent oxidation of the adducts affords a versatile platform for the preparation of various diaminopyrimidines with five points of diversity. The whole sequence may be performed as a one-pot process.

Key words

Ugi-Smiles - thiouracil - isocyanide - diaminopyrimidines - SNAr

    References and Notes

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7

All previous reported Ugi-Smiles couplings of pyrimidines have only been performed on monohydroxy or mono-mercapto derivatives,6 as a second electron-donating group was expected to lower the efficiency of the Smiles step.