Ethyl orthoformate → 7-Chloropyrido[3,2-d]pyrimidin-4(3H)-one

HRID 1517401Notes

Reaction equation

HRID 1517401 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([NH2:11])=[O:10])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH:12](OCC)(OCC)OCC>>[Cl:8][C:6]1[CH:5]=[N:4][C:3]2[C:9](=[O:10])[NH:11][CH:12]=[N:1][C:2]=2[CH:7]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 218200583-Amino-5-chloropyridine-2-carboxamide

Product 1

HCID 1357416377-Chloropyrido[3,2-d]pyrimidin-4(3H)-one

Procedure

A suspension of 3-amino-5-chloro-pyridine-2-carboxamide (3.43 g, 20 mmole) in triethyl orthoformate (50 ml) was refluxed for 3 hours. After cooling to room temperature, the precipitate was collected by filtration and washed with hexane. The title compound was obtained as a white solid (3.4 g, yield 94%) which was characterized by its mass spectrum as follows: MS (m/z): 182.1 ([M+H]+, 100).

Workup

  1. temperaturewas refluxed for 3 hours
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with hexane

Sources & evidence

ORD record
ord-171b5364bd8a485b9ef57c9334802ff8
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

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