Synlett 2019; 30(17): 2000-2003
DOI: 10.1055/s-0039-1690183
letter
© Georg Thieme Verlag Stuttgart · New York

Efficient Halogenation of 2-Aminopyrazine

Enric Lizano
,
Josep Grima
,
M. Dolors Pujol
Laboratori de Química Farmacèutica, Facultat de Farmàcia i Ciències de l’Alimentació, University of Barcelona, Campus Diagonal, Av. Joan XXIII, 27–31, 08028 Barcelona, Spain   eMail: mdpujol@ub.edu
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Publikationsverlauf

Received: 27. Juni 2019

Accepted after revision: 02. August 2019

Publikationsdatum:
11. September 2019 (online)


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Abstract

2-Aminopyrazine was halogenated with NIS, NCS, and NBS under different reaction conditions. Chlorination and bromination were achieved with good yields by using acetonitrile as the solvent. However, iodination was only obtained in poor yields. Undoubtedly, the best conditions for both mono- and dihalogenation were the use of NBS, acetonitrile, and microwave assistance for short periods. 3,5-Dibromo-2-aminopyrazine is an excellent functionalized starting material for the synthesis of nitrogen heterocycles.

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