4-Chloro-2-chloromethyl-3,5-dimethylpyridinium chloride → 5-methoxy-2-[(4-chloro-3,5-dimethyl-2-pyridinyl)methylthio]-1H-imidazo[4,5-b]pyridine

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Reaction Steps

As a further example, 4-chloro-2-chloromethyl-3,5-dimethylpyridinium chloride could be reacted with 5-methoxy-1H-imidazo[4,5-b]pyridine-2-thiol according to the procedure described under Example 39 to give 5-methoxy-2-[(4-chloro-3,5-dimethyl-2-pyridinyl)methylthio]-1H-imidazo[4,5-b]pyridine. Conversion of this product with methanol-d4 following the protocol described under Example 44 would then give rise to formation of 5-methoxy-2-[(3,5-dimethyl-4-trideuteriomethoxy-2-pyridinyl)methylthio]-1H-imidazo[4,5-b]pyridine, which, in turn, could be oxidized according to the procedure used in Example 46 to rac-5-methoxy-2-[(3,5-dimethyl-4-trideuteriomethoxy-2-pyridinyl)methylsulfinyl]-1H-imidazo[4,5-b]pyridine.

Provenance & Evidence