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Paper | Regular issue | Vol 36, No. 8, 1993, pp.1897-1908
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6400
Syntheses of a Regioisomer of N-{4-[2-(2-Amino-4(3H)-oxo-7H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic Acid (LY231514), an Active Thymidylate Synthase Inhibitor and Antitumor Agent

Edward C. Taylor,* Wendy B. Young, Rajendra Chaudhari, and Hemantkumar H. Patel

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

Abstract

Two independent routes to N-{4-[2-[2-amino-4(3H)-oxo-7H-pyrrolo[2,3-d]pyrimidin-6-yl)ethyl]benzoyl}-L-glutamic acid, a regioisomer of the potent TS inhibitor and antitumor agent LY231514, are described. Preliminary in vitro cell culture evaluation has shown that attachment of the ethanobenzoylglutamate moiety of LY231514 to postition 6 of the pyrrolopyrimidine ring system rather than to position 5 results in complete loss of biological activity.