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Paper | Regular issue | Vol 32, No. 7, 1991, pp.1327-1340
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5743
An Intramolecular 1,3-Dipolar Cycloaddition Approach to 5,6,7,8-Tetrahydro-4-ethoxy-6-hydroxymethyl-2-pivaloylamino-5-deazapteridin-5(8H)-one, a Potentially Useful Intermediate to 5-Deaza- and 5,10-Dideaza-5,6,7,8-tetrahydrofolic Acid Analogs

Edward C. Taylor* and Partha S. Ray

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

Abstract

2-Amino-4,6-dichloro-5-formylpyrimidine was converted to the title compound (12), a potentially useful intermediate for the synthesis of 5-deaza- and 5,10-dideaza-5,6,7,8-tetrahydrofolic acid analogs. The key steps in the sequence were an intramolecular 1,3-dipolar cycloaddition of an in situ generated nitrile oxide (10b) to give the isoxazolo[3’,4’:4,5]pyrido[2,3-d]pyrimidine (11b) followed by reductive cleavage of the isoxazoline N-O bond.