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Synthesis and Structure of Novel Thieno[2, 3‐ d ]Pyrimidine Derivatives Containing 1, 3, 4‐Oxadiazole Moiety
Author(s) -
Ho YuhWen,
Suen MawCherng
Publication year - 2009
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200900060
Subject(s) - chemistry , pyrimidine , sodium methoxide , medicinal chemistry , moiety , pyridine , yield (engineering) , methyl iodide , oxadiazole , stereochemistry , organic chemistry , methanol , materials science , metallurgy
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‐phenyl‐thieno[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.