Synthesis of 7-aza-5,8,10-trideazafolic acid and its 4-amino-derivative as potential antifolates

o-Aminoamide 8, an intermediate in our multistep synthesis of the tide compounds was prepared from 1,3-diketone 3. The following condensation of 8 with chloroformamidine-HCl (9) gave pyrido[3,4-d]pyrimidine 10. Dehydratisation of amide 8 led to o-aminonitrile 15, which was cyclocondensated with guan...

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Bibliographic Details
Published inJournal of heterocyclic chemistry Vol. 39; no. 6; pp. 1195 - 1200
Main Authors Wollein, G, Troschutz, R
Format Journal Article
LanguageEnglish
Published PROVO HETERO CORPORATION 01.11.2002
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
METHOTREXATE
ANALOGS
LY231514
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Summary:o-Aminoamide 8, an intermediate in our multistep synthesis of the tide compounds was prepared from 1,3-diketone 3. The following condensation of 8 with chloroformamidine-HCl (9) gave pyrido[3,4-d]pyrimidine 10. Dehydratisation of amide 8 led to o-aminonitrile 15, which was cyclocondensated with guanidine (16) to yield pyrido[3,4-d]pyrimidine-2,4-diamine 17. Coupling of the acids 11 and 18 with diethyl L-glutamate (12) and following saponification provided 7-aza-5,8,10-trideazafolic acid 14 and its 4-amino-derivative 26.
ISSN:0022-152X
DOI:10.1002/jhet.5570390613