2,3-Lutidine → 5-BROMO-2,3-DIMETHYLPYRIDINE

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Reaction Steps

2,3-Dimethylpyridine is treated with bromine in oleum to give 3-bromo-5,6-dimethylpyridine which is converted into a Grignard reagent, and this is treated with ethyl orthoformate and the product hydrolysed to give 5,6-dimethylpyridine-3-carboxaldehyde. This aldehyde is condensed with malonic acid and the product is hydrogenated and esterified to give ethyl β-(5,6-dimethyl-3-pyridyl)propionate. Substitution of this ester for ethyl β-(3-pyridyl)propionate in the procedure of Example 6 and fusion of the product with 2-(5-methyl-4-imidazolylmethylthio)ethylamine gives 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-5-(5,6-dimethyl-3-pyridylmethyl)-4-pyrimidone.

Provenance & Evidence