Synthesis and reduction of 6-nitroso-5,7-dimethyl-4,7 dihydro[1,2,4]triazolo[1,5-a]pyrimidine
Abstract
Nitrosation of 5,7-dimethyl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine leads, with a moderate yield, to the formation of 6-nitrososubstituted derivative, a promising compound for the synthesis of low-molecular building blocks, based on 6-amino-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine. When 6-nitrosoderivative reacts with NaBH4, the reduction of dihydropyrimidine cycle takes place, while as NO-group remains unaffected, however, the reduction product exists as the oxime of 6-keto-5,7-dimethyl-4,5,6,7-tetrahydro[1,2,4]triazolo[1,5-a]pyrimidine, which chemical structure was unambiguously proved by deuterium exchange experiment in 1H NMR spectra.
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