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  • Title: Convenient synthesis of 10-deazaaminopterin via a pteridine ylide.
    Author: Piper JR, Montgomery JA.
    Journal: J Med Chem; 1980 Mar; 23(3):320-1. PubMed ID: 7365749.
    Abstract:
    10-Deazaaminopterin, a potential antitumor agent now undergoing clinical trials, has been synthesized by a new approach involving the Wittig reaction. The ylide obtained by reaction of 6-(bromomethyl)-2,4-pteridinediamine with triphenylphosphine in Me2NAc, followed by treatment with NaOMe, underwent smooth reaction with diethyl N-(4-formylbenzoyl)-L-glutamate to give the vinyl precursor of the subject compound. Catalytic hydrogenation (Pt in glacial AcOH) of this product at ambient conditions led to uptake of 3 molar equiv of H2. Exposure to air during saponification of the ester groupings apparently gave the 7,8-dihydro compound according to UV spectral data, and further oxidation with H2O2 led to 10-deazaaminopterin.
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