Synthesis and antifolate properties of 9-alkyl-10-deazaminopterins.

  title={Synthesis and antifolate properties of 9-alkyl-10-deazaminopterins.},
  author={J. Degraw and P. H. Christie and R. Kisliuk and Y. Gaumont and F. Sirotnak},
  journal={Journal of medicinal chemistry},
  volume={33 1},
Reformatski condensation of benzyl 2-bromopropionate with 4-carbomethoxybenzaldehyde, followed by dehydration afforded benzyl 2-methyl-p-carbomethoxycinnamate (4a). Hydrogenation over a Pd catalyst gave the hydrocinnamic acid 5a. Conversion to the chloromethyl (6a) and azidomethyl ketone (7a) was followed by hydrogenation to the aminomethyl ketone (8a). Direct N-alkylation by 2,4-diamino-5-nitro-6-chloropyrimidine followed by reductive ring closure in Zn-HOAc and subsequent saponification of… Expand
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