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

HRID 19619

Reaction equation

HRID 19619 reaction equation
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][C:12](=O)[CH:11]([C:16]([O:18]CC)=O)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(O)(=O)C.[CH:25]([NH2:27])=[NH:26]>>[CH2:2]([N:9]1[CH2:14][CH2:13][C:12]2=[N:27][CH:25]=[N:26][C:16](=[O:18])[CH:11]2[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 102623Ethyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochlorideHCID 160693Formamidine acetate

Product 1

HCID 668710506-Benzyl-5,6,7,8-tetrahydropyrido[4,3-D]pyrimidin-4(4AH)-one

Procedure

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 substitiuted 5,6,7,8-tetrahydro-6-(5-methylpyridin-2-yl)pyrido[4,3-d]pyrimidines.

Sources & evidence

ORD record
ord-fd240aa3da6d4d00ad9a6a0200f0d1f0
Source dataset
uspto-grants-2010_06
Patent number
US07745451B2

Linked notes

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