Chemoselective Demethylation of Methoxypyridine

A chemoselective demethylation method for various methoxypyridine derivatives has been developed. Treatment of 4-methoxypyridine with L-selectride in THF for 2 h at reflux temperature afforded 4-hydroxypyridine in good yield; no reaction to anisole occurred. The utility of our method was demonstrate...

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Bibliographic Details
Published inSynlett Vol. 30; no. 8; pp. 951 - 954
Main Authors Makino, Kosho, Hasegawa, Yumi, Inoue, Takahide, Araki, Koji, Tabata, Hidetsugu, Oshitari, Tetsuta, Ito, Kiyomi, Natsugari, Hideaki, Takahashi, Hideyo
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.05.2019
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
REAGENT
O-DEMETHYLATION
ACID
pyridine
OMEPRAZOLE
DEPROTECTION
REGIOSELECTIVITY
CLEAVAGE
demethylation
ALKYL ARYL ETHERS
REDUCTION
chemoselective
anisole
L-selectride
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Summary:A chemoselective demethylation method for various methoxypyridine derivatives has been developed. Treatment of 4-methoxypyridine with L-selectride in THF for 2 h at reflux temperature afforded 4-hydroxypyridine in good yield; no reaction to anisole occurred. The utility of our method was demonstrated by the efficient synthesis of the metabolic substances of the antiulcer agent omeprazole. Chemoselective demethylation at the site of 3,5-dimethyl-4-methoxypyridine in the presence of 4-methoxybenzimidazole was achieved.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0037-1612427