The reaction of 5-(1-pyrrolyl)-4-methyl-2-phenylthieno[2,3-d]pyrimidine carbohydrazide 5 with CS 2 in the presence of pyridine afforded the 6-(2,3-dihydro-2-mercapto-1,3,4-oxadiazol-5-yl)-4-methyl-5-(1-pyrrolyl)-2-phenylthieno[2,3-d]pyrimidine 6, which reacted with methyl iodide in the presence of sodium methoxide to yield the 6-(2-methylthio-1,3,4-oxadiazol-5-yl)-4-methyl-5-(1-pyrrolyl)-2-phenylthieno[2,3-d]pyrimidine 7. The 6-(2-substituted-1,3,4-oxadiazol-5-yl)-2-phenylthieno[2,3-d]pyrimidine derivatives 9, 11 and 13 were obtained by the condensation of 6-(2-methylthio-1,3,4-oxadiazol-5-yl)-2-phenylthieno[2,3-d]pyrimidine 7 with appropriate secondary amines. The structure of the new compounds was substantiated from their IR, UV-vis spectroscopy, 1 H NMR, mass spectra, elemental analysis and X-ray crystal analysis.
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