Diethyl Ether → 5-(Pyrimidin-4-yl)pyridin-2(1H)-one

HRID 1388653Notes

Reaction equation

HRID 1388653 reaction equation
[O:1]=[C:2]1[NH:10][CH:9]=[C:8]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][N:12]=2)[CH:7]=[C:3]1C(O)=O.CCOCC>N1C2C(=CC=CC=2)C=CC=1>[N:14]1[CH:15]=[CH:16][C:11]([C:8]2[CH:7]=[CH:3][C:2](=[O:1])[NH:10][CH:9]=2)=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 132766752-Oxo-5-(pyrimidin-4-yl)-1,2-dihydropyridine-3-carboxylic acid

Product 1

HCID 132766775-(Pyrimidin-4-yl)pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 7047QuinolineSolvent

Procedure

A solution of 90.8 g of 1,2-dihydro-2-oxo-5-(4-pyrimidinyl) nicotinic acid in 900 ml of quinoline is refluxed overnight. The reaction mixture is cooled, poured into 1800 ml of anhydrous ether, stirred for 30 minutes, filtered and the filtered solid washed with 2 l of ether. The solid is dried, recrystallized from 100 ml of hot dimethylformamide and dried to yield 5-(4-pyrimidyl)-2(1H)-pyridone, M.P. >250° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationfiltered
  3. washthe filtered solid washed with 2 l of ether
  4. customThe solid is dried
  5. customrecrystallized from 100 ml of hot dimethylformamide
  6. customdried

Sources & evidence

ORD record
ord-485a5de5e6b84481b25b6cb6cda88093
Source dataset
uspto-grants-1984_02
Patent number
US04432979

Reaction notes

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