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Paper | Regular issue | Vol 43, No. 2, 1996, pp.349-365
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7269
Synthesis of Thieno[2,3-d]pyrimidine Analogues of the Potent Antitumor Agent N-{4-[2-(2-Amino-4(3H)-oxo-7H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic Acid (LY231514)

Edward C. Taylor ,* Hemantkumar H. Patel, Gowravaram Sabitha, and Rajendra Chaudhari

*Department of Chemistry, Princeton University, Princeton, NJ 08544, U.S.A.

Abstract

Several thieno[2,3-d]pyrimidine analogues of the potent antitumor agent N-{4-[2-(2-amino-4(3H)-oxo-7H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic acid (LY231514,7) have been prepared by two different strategies. The first involved S-alkylation of the 6-mercaptopyrimidines (13) and (14) with the α-haloketone (12), followed by cyclization to the thienopyrimidines (17) and (18) respectively. The second involved synthesis of the 2-amino-3-carbomethoxy- and 2-amino-3-cyano-thiophenes (19) and (20) which wre cyclized with acetonitrile to the corresponding thienopyrimidines (21) and (22). Compounds (17, 18, 21, and 22) were hydrolyzed to the acids which were coupled with dimethyl L-glutamate, and the resulting monopeptide esters were saponified to the target analogs.