Synthesis 2016; 48(23): 4246-4252
DOI: 10.1055/s-0035-1562788
paper
© Georg Thieme Verlag Stuttgart · New York

Ultrasound-Promoted Synthesis of 4-Pyrimidinols and Their Tosyl Derivatives

Matías Vidal
Facultad de Química y Biología, Universidad de Santiago de Chile, Av. Bernardo O’Higgins 3363, Santiago, Chile   eMail: moises.dominguez@usach.cl
,
Macarena García-Arriagada
Facultad de Química y Biología, Universidad de Santiago de Chile, Av. Bernardo O’Higgins 3363, Santiago, Chile   eMail: moises.dominguez@usach.cl
,
Marcos Caroli Rezende
Facultad de Química y Biología, Universidad de Santiago de Chile, Av. Bernardo O’Higgins 3363, Santiago, Chile   eMail: moises.dominguez@usach.cl
,
Moisés Domínguez*
Facultad de Química y Biología, Universidad de Santiago de Chile, Av. Bernardo O’Higgins 3363, Santiago, Chile   eMail: moises.dominguez@usach.cl
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Publikationsverlauf

Received: 15. Juni 2016

Accepted after revision: 27. Juni 2016

Publikationsdatum:
17. August 2016 (online)


Abstract

Ultrasound irradiation promoted the cyclocondensation of β-keto esters and amidines in good to excellent yields to form sixteen highly substituted 4-pyrimidinols. Tosylation of these compounds, in another ultrasound-promoted conversion, formed 4-pyrimidyl tosylates in high yields. The use of the developed protocol as an alternative route to 4-arylpyrimidines was illustrated with three examples of the Suzuki–Miyaura cross-coupling of the prepared tosylates with phenylboronic acid.

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