Syntheses of 2-amino-4, 6-dichloro-5-nitropyrimidine and 2-amino-4, 5, 6-trichloropyrimidine: an unusual aromatic substitution

S Lopez, T McCabe, RS McElhinney, TBH McMurry…

Index: Lopez, Sergio; McCabe, Thomas; Stanley McElhinney; McMurry, T. Brian H.; Rozas, Isabel Tetrahedron Letters, 2009 , vol. 50, # 44 p. 6022 - 6024

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Citation Number: 2

Abstract

2-Amino-4, 6-dichloro-5-nitropyrimidine is an intermediate required for the preparation of nitropyrimidines as inactivators of the DNA repairing protein MGMT. When attempting its synthesis, 2-amino-4, 5, 6-trichloropyrimidine is obtained instead, via unusual aromatic substitution of the nitro group in 2-amino-4-hydroxy-5-nitropyrimidin-6-one by chloride. The synthesis, the reactivity of 4, 5, 6-trichloropyrimidine and the efficient preparation of 2- ...