Efficient and Selective Demethylation of Heteroaryl Methyl Ethers in the Presence of Aryl Methyl Ethers

Ajay Soni Department of Medicinal Chemistry, New Drug Discovery Research, Ranbaxy Research Laboratories, Gurgaon, Haryana, IndiaCorrespondence[email protected]

Akhilesh Dutt Department of Medicinal Chemistry, New Drug Discovery Research, Ranbaxy Research Laboratories, Gurgaon, Haryana, India

Viswajanani Sattigeri Department of Medicinal Chemistry, New Drug Discovery Research, Ranbaxy Research Laboratories, Gurgaon, Haryana, India

Ian A. Cliffe Department of Medicinal Chemistry, New Drug Discovery Research, Ranbaxy Research Laboratories, Gurgaon, Haryana, India

Pages 1852-1857 | Received 05 Feb 2010, Published online: 29 Apr 2011

Cite this article
https://doi.org/10.1080/00397911.2010.493262

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Abstract

A new and efficient method for the demethylation of 6-membered aza-heterocyclic methyl ethers is described using lithium chloride and para-toluenesulfonic acid. This process is chemoselective for aza-heterocyclic methyl ethers in the presence of aryl methyl ethers.

Keywords:

Demethylation
lithium chloride
2-methoxypyrdidine
p-toluenesulfonic acid
pyridine-2-one

ACKNOWLEDGMENTS

We thank the Analytical Chemistry Department of New Drug Discovery Research, Ranbaxy Research Laboratories, for spectral and chromatographic data. We also thank Dr. Jitendra Sattigeri for helpful suggestions and comments.

Notes

^aThe reactions were quenched after 30 min, and the extent of reaction was determined by HPLC.

^aAll products were purified by column chromatography and characterized by ¹H NMR and mass spectroscopy.

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