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Paper | Regular issue | Vol 75, No. 3, 2008, pp.555-569
Published online, 16th November, 2007
DOI: 10.3987/COM-07-11232
Synthesis of the Azathioprine Analogs

Alicja Kowalska* and Krystina Pluta

*Department of Organic Chemistry, The Medical University of Silesia, Jagiellonska 4, 41-200 Sosnowiec, Poland

Abstract

The effective synthesis of the azathioprine analogs - 2-subsituted derivatives of 7-methyl-6-(1-methyl-4-nitroimidazol-5-ylthio)purines 5 has been achieved by the reaction of 2-subsituted 6-purinethiones 4 with 5-chloro-1-methyl-4-nitroimidazole in ethanol. In the case of 7-methyl-2,6-dithioxanthine 4j, reaction in DMF gave di(imidazolyl) product 5l. The key step in this synthesis was preparation of the appropriate 2-substituted 6-purinones 2 and 6-chloropurines 3 which were further converted to 6-purinethione 4.