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Investigations into the synthesis of 6‐ethyl‐5‐(4‐pyridinyl)‐2,4‐pyrimidinediamine as a potential antimalarial agent
Author(s) -
Hung Jocelyn,
Werbel Leslie M.
Publication year - 1984
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570210321
Subject(s) - chemistry , guanidine , yield (engineering) , alkylation , propionate , pyridine , antimalarial agent , condensation , organic chemistry , pyrimethamine , pyrimidine , combinatorial chemistry , stereochemistry , malaria , plasmodium falciparum , materials science , thermodynamics , physics , immunology , metallurgy , biology , catalysis
The synthesis of 6‐ethyl‐5‐(4‐pyridinyl)‐2,4‐pyrimidinediamine ( 2 ), the pyridine analog of pyrimethamine, is described. Condensation of 4‐pyridineacetonitrile ( 3 ) with methyl propionate afforded α‐(1‐oxopropyl)‐4‐pyridineacetonitrile ( 4 ). Treatment with triethyl orthopropionate gave primarily the undesired N ‐alkylated material. However reaction of the crude mixture with guanidine afforded 2 in low yield. This material was devoid of significant antimalarial activity.