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Paper | Regular issue | Vol 26, No. 10, 1987, pp.2673-2676
Published online, 1st January, 1970
DOI: 10.3987/R-1987-10-2673
Synthesis and Structural Confirmation of 5,6-Cyclopenteno-5-deazapterin

Edward C. Taylor and John C. Warner

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

Abstract

Condensation of 2,4-diamino-6(1H)-pyrimidinone with 1-formyl-1-cyclopentene in 60% acetic acid gives 5,6-cyclopenteno-5-deazapterin (2). The 2-pivaloyl derivative of 2 was then synthesized in an unequivocal manner by Diels-Alder cycloaddition of 2-pivaloylamino-7-methylthio-6-azapterin (3) with 1-(N-morpho1ino)cyclopentene to give 5,6-cyclopenteno-2-pivaloylamino-7-methylthio-5-deazapterin (4), followed by Raney nickel desulfurization.