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Synthesis of 4-methoxy-2,3,5-trimethylpyridine: A Specific Building Block for Compounds With Gastric-Acid Inhibiting Activity

Synthesis of 4-methoxy-2,3,5-trimethylpyridine: A Specific Building Block for Compounds With Gastric-Acid Inhibiting Activity

M Mittelbach, H W Schmidt, G Uray, H Junek, B Lamm, K Ankner, A Brändström, R Simonsson

Acta Chem Scand B. 1988 Sep;42(8):524-9.

PMID: 3227742

Abstract:

A new synthesis of 4-methoxy-2,3,5-trimethylpyridine (2), an important building block for the preparation of gastric-acid inhibiting compounds, is described. Condensation of ethyl 3-amino-2-methyl-2-butenoate (3) and diethyl 2-methylmalonate (4) gives 4-hydroxy-3,5,6-trimethyl-2(1H)-pyridone 5. Reaction of 5 with phosphoryl chloride affords 2,4-dichloro-3,5,6-trimethylpyridine (9a), which, upon hydrogenolysis with palladium on charcoal, gives 2,3,5-trimethylpyridine (10). However, selective hydrogenolysis in acidic solution yields 4-chloro-2-3-5-trimethylpyridine (11). Substitution of the chlorine in 11 with methoxide ion gives 4-methoxy-2,3,5-trimethylpyridine (2), which can be oxidized to the corresponding N-oxide (13). This constitutes a new and efficient route to compound 2 in an overall yield of 43%.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP871126204	4-Methoxy-2,3,5,6-tetrafluorophenylboronic acid		871126-20-4	Price

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