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Synthesis and antimalarial properties of 2,4‐diamino‐6‐[(aryl)thio, sulfinyl, and sulfonyl]pyrido[3,2‐ d ]pyrimidines
Author(s) -
Colbry Norman L.,
Elslager Edward F.,
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.5570210556
Subject(s) - chemistry , sulfonyl , nitration , aryl , thio , medicinal chemistry , cyanide , derivative (finance) , nitro , pyrimidine , organic chemistry , stereochemistry , alkyl , financial economics , economics
The synthesis and antimalarial activity of a series of 2,4‐diamino‐6‐[(aryl)thio, sulfinyl and sulfonyl]pyrido‐[3,2‐ d ]pyrimidines is described. Nitration of 2,6‐dichloropyridine provided the 3‐nitro derivative which was converted to 6‐chloro‐3‐nitro‐2‐pyridinecarbonitrile (V) with cuprous cyanide. Condensation of an aryl thiol with V gave the 6‐arylthiopyridines VI which were reduced with iron in hydrochloric acid and condensed with chloroformamidine to give the 6‐arylthiopyrido[3,2‐ d ]pyrimidin‐2,4‐diamines X. Alternatively V was reduced to the amine VIII condensed with chloroformamidine and the resulting 6‐chloropyrido[3,2‐ d ]pyrimidine (IX) was treated with an arylthiol. Oxidation of X provided sulfinyl and sulfonyl analogs.