Ethyl Acrylate → 5,8-Dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-amine

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Reaction Steps

In U.S. Pat. No. 5,858,924, 2-amino-5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine is prepared from 3-amino-8-methoxy-5-methylthio[1,2,4]triazolo-[4,3-c]pyrimidine by treatment with ethyl acrylate and sodium methoxide in methanol. The 3-amino-8-methoxy-5-methylthio[1,2,4]triazolo[4,3-c]pyrimidine in turn is prepared from 5-methoxy-4-chloro-2-methylthio-pyrimidine by treatment with hydrazine followed by cyclization with cyanogen bromide. It would be advantageous to produce 2-amino-5,8-dimethoxy[1,2,4]-triazolo[1,5-c]pyrimidine more efficiently and in higher yield. It would also be advantageous to avoid the use of methylthio containing intermediates and the use of ethyl acrylate in the rearrangement of a [1,2,4]triazolo[4,3-c]pyrimidine into a [1,2,4]-triazolo[1,5-c]pyrimidine.

Provenance & Evidence