Abstract
3-Cyano-4,6-bis(methylthio)pyrazolo[3,4-d]pyrimidine was synthesized by cyclization of 3,4-dicyano-5-aminopyrazole with CS2 in pyridine with subsequent Dimroth rearrangement and methylation of the resulting 3-cyano-4,6-dimercaptopyrazolo[3,4-d]-pyrimidine with methyl iodide. Glycosylation of the product by fusion with 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose in the presence of iodine gave 1-(2′,3′,5′-tri-O-acetyl-β-D-ribofuranosyl)-3-cyano-4,6-bis(methylthio)pyrazolo[3,4-d]pyrimidine, the deacetylation of which with a 1% solution of hydrogen chloride in methanol led to 3-cyano-4,6-bis(methylthio)pyrazolo[3,4-d]pyrimidine 1-fiboside. The structures of the compounds were established by IR, UV, circular dichroism, PMR, and 13NMR spectroscopy.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1687–1692, December, 1979.
Original article submitted March 29, 1979.
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Korbukh, I.A., Bulychev, Y.N. & Preobrazhenskaya, M.N. Synthesis of 3-Cyano-4,6-bis(methylthio)pyrazolo[3,4-d]pyrimidine 1-riboside. Chem Heterocycl Compd 15, 1361–1366 (1979). https://doi.org/10.1007/BF00514744
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DOI: https://doi.org/10.1007/BF00514744