Ethyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochloride → 6-Benzyl-5,6,7,8-tetrahydropyrido[4,3-D]pyrimidin-4(4AH)-one

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Reaction Steps

Various 6 substituted 5,6,7,8-tetrahydro-6-(5-methylpyridin-2-yl)pyrido[4,3-d]pyrimidines are prepared using a general procedure shown above. Ethyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochloride is reacted with formamidine acetate to yield 6-benzyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(4aH)-one, which, in turn, is reduced to 5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one. The intermediate coupled with 5 chloro 2 methyl pyridine to produce 5,6,7,8-tetrahydro-6-(5-methylpyridin-2-yl)pyrido[4,3-d]pyrimidin-4(3H)-one. Chlorination of the resulting product using POCl3 and displacement of the chloride using various benzylamines via microwave displacement will afford various 6 substituted 5,6,7,8-tetrahydro-6-(5-methylpyridin-2-yl)pyrido[4,3-d]pyrimidines.

Provenance & Evidence