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Synthesis of 5‐ethynylorotic acid
Author(s) -
Bhatt Ram S.,
Kundu Nitya G.,
Chwang T. Ling,
Heidelberger Charles
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.5570180428
Subject(s) - chemistry , sodium methoxide , tetrahydrofuran , reagent , aldehyde , oxalyl chloride , trimethylsilyl , aqueous solution , oxidizing agent , hydrolysis , sodium hydroxide , derivative (finance) , organic chemistry , sodium , condensation , dimethyl sulfoxide , medicinal chemistry , methanol , catalysis , physics , solvent , financial economics , economics , thermodynamics
Condensation of 2,4‐dimethoxy‐5‐iodo‐6‐carbomethoxypyrimidine ( 10 ) with copper (I) 3‐tetrahydropyranyloxyprop‐1‐ynide ( 4 ) afforded 2,4‐dimethoxy‐5‐(3′‐tetrahydropyranyloxyprop‐1′‐yn)‐6‐carbomethoxypyrimidine ( 11 ), which was hydrolyzed to produce 2,4‐dimethoxy‐5‐(3′‐hydroxyprop‐1′‐yn)‐6‐carbomethoxypyrimidine ( 12 ). Oxidation of 12 with dimethyl sulfoxide‐oxalyl chloride reagent gave the acetylenic aldehyde ( 13 ), which on treatment with sodium methoxide in dry tetrahydrofuran yielded 2,4‐dimethoxy‐5‐ethynyl‐6‐carbomethoxypyrimidine ( 14 ). The trimethylsilyl derivative ( 15 ) was deprotected by sequential treatment with iodotrimethylsilane and aqueous sodium hydroxide, leading to the formation of 5‐ethynylorotic acid ( 1 ).
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