Regioselective Synthesis of Pyrrolo[2,3-d]pyrimidine Derivatives by Amine Oxide Rearrangement

Abstract

Regioselective synthesis of biologically important pyrrolo[2,3-d]pyrimidine derivatives 4a-h in 75-82% yields are reported. The applied conditions of the less studied rearrangement are the oxidation of 6-N-(4-aryloxybut-2-yn-1-yl)-N-methyl(or ethyl)amino-1,3-dimethyluracils 3a-h with m-chloroperoxybenzoic acid at 0-5 °C for one hour and then stirring at room temperature for 10-12 hours. Compounds 3a-h are prepared by the reaction of 1,3-di­methyl-6-chlorouracil (1) with different (4-aryloxybut-2-yn-1-yl)-N-methylamines or (4-aryloxybut-2-yn-1-yl)-N-ethylamines 2 in refluxing ethanol for 12-14 hours.

Key words

6-alkylamino-1,3-dimethyluracils - m-chloroperoxybenzoic acid - amine oxide rearrangement - pyrrolo[2,3-d]pyri­midines - [2,3] and [3,3] sigmatropic rearrangement

References

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