Triethyl orthoacetate → 6-(4-Fluorophenyl)-2-methylpyrido[3,2-d]pyrimidin-4(1H)-one

HRID 1517447Notes

Reaction equation

HRID 1517447 reaction equation
[NH2:1][C:2]1[C:3]([C:15]([NH2:17])=[O:16])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1.[C:18](OCC)(OCC)(OCC)[CH3:19]>>[CH3:18][C:19]1[NH:17][C:15](=[O:16])[C:3]2[N:4]=[C:5]([C:8]3[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=3)[CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

3

Reactant 2

HCID 66221Triethyl orthoacetateHCID 596479063-Amino-6-(4-fluorophenyl)picolinamide

Product 1

HCID 1360008926-(4-Fluorophenyl)-2-methylpyrido[3,2-d]pyrimidin-4(1H)-oneYield 70%

Procedure

A suspension of 3-amino-6-(4-fluorophenyl)-pyridine-2-carboxylic acid amide (0.46 g, 2.0 mmol) in triethyl orthoacetate (10 ml) was heated under reflux for 3 hours. After cooling to room temperature, the precipitate was collected by filtration and washed with diethyl ether, yielded the title compound as a white solid (360 mg, yield 70%) which was characterised as follows: MS (m/z): 256 ([M+H]+, 100).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-6df778c46d7744bba60b72b17e51d866
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

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