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Synthesis and antimicrobial testing of 2‐amino‐6‐hydroxymethyl‐4‐(3 H )pyrido[3,2‐ d ]pyrimidinone
Author(s) -
Kelley James L.,
Mclean Ed W.
Publication year - 1981
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.5570180405
Subject(s) - chemistry , sodium borohydride , hydroxymethyl , antimicrobial , aldehyde , catalysis , stereochemistry , organic chemistry
Synthesis of 2‐amino‐6‐hydroxymethyl‐4‐(3 H )pyrido[3,2‐ d ]pyrimidinone ( 5 ) from 2‐amino‐6‐methyl‐4‐(3 H )‐pyrido[3,2‐ d ]pyrimidinone ( 2 ) was accomplished by selenium dioxide oxidation of 2 to the aldehyde 4 followed by sodium borohydride reduction. Compound 2 was available in four steps from 5‐aminouracil or in two steps from 5‐nitroisocytosine ( 3a ). Catalytic reduction of 4 or 5 gave a mixture of 2‐amino‐6‐methyl‐5,6,7,8‐tetrahydro‐4‐(3 H )pyrido[3,2‐ d ]pyrimidinone ( 6a ) and the 6‐hydroxymethyl compound 6b . These compounds showed only weak inhibitory activity in the coupled reactions catalyzed by 7,8‐dihydro‐6‐hydroxymethylpterin pyrophosphokinase and 7,8‐dihydropteroate synthetase from E. Coli . No significant antibacterial activity was observed.