Synthesis 2015; 47(24): 3947-3955
DOI: 10.1055/s-0035-1560470
paper
© Georg Thieme Verlag Stuttgart · New York

Highly Regioselective Synthesis of 3,6-Disubstituted 2-(Methylsulfanyl)pyrimidin-4(3H)-ones

Josiane M. dos Santos
Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, Brazil   Email: nilo.zanatta@ufsm.br
,
Alessandra S. da Silveira
Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, Brazil   Email: nilo.zanatta@ufsm.br
,
Laura A. Souza
Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, Brazil   Email: nilo.zanatta@ufsm.br
,
Marcio M. Lobo
Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, Brazil   Email: nilo.zanatta@ufsm.br
,
Helio G. Bonacorso
Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, Brazil   Email: nilo.zanatta@ufsm.br
,
Marcos A. P. Martins
Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, Brazil   Email: nilo.zanatta@ufsm.br
,
Nilo Zanatta*
Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, Brazil   Email: nilo.zanatta@ufsm.br
› Author Affiliations
Further Information

Publication History

Received: 06 July 2015

Accepted after revision: 13 August 2015

Publication Date:
16 September 2015 (online)


Abstract

This study reports a simple and highly regioselective synthesis of a new series of 3,6-disubstituted 2-(methylsulfanyl)pyrimidin-4(3H)-ones, in which the 6-substituents are methyl or aryl groups and the 3-substituents are alkyl, allyl, phenyl, benzyl, or 2-phenylethyl groups. The products are obtained in good yields by cyclocondensation of the appropriate 4-substituted 4-methoxy-1,1,1-trichloroalk-3-en-2-ones with nonsymmetric 1-substituted 2-methylisothiourea sulfates under mild basic conditions.

Supporting Information

 
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