Ethyl Bromide → 3-Bromo-1-ethyl-5-(pyrimidin-4-yl)pyridin-2(1H)-one

HRID 1388656Notes

Reaction equation

HRID 1388656 reaction equation
C[O-].[Na+].[Br:4][C:5]1[C:6](=[O:17])[NH:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][N:12]=2)[CH:10]=1.Br[CH2:19][CH3:20]>CN(C=O)C.CO.O>[Br:4][C:5]1[C:6](=[O:17])[N:7]([CH2:19][CH3:20])[CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][N:12]=2)[CH:10]=1

Participants

7

Reactant 3

HCID 6332Ethyl BromideHCID 10942334Sodium MethoxideHCID 132766783-Bromo-5-(pyrimidin-4-yl)pyridin-2(1H)-one

Product 1

HCID 136450963-Bromo-1-ethyl-5-(pyrimidin-4-yl)pyridin-2(1H)-one

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

A solution of 1.9 g of sodium methoxide in 100 ml of DMF and 30 ml MeOH is added to a suspension of 8.0 g of 3-bromo-5-(4-pyrimidinyl)-2(1H)-pyridone in 100 ml of DMF. Bromoethane (2.7 ml) is added to the mixture, and the mixture is heated to 70° C. for 2 hours. After cooling the mixture to RT, the solvent is evaporated leaving a solid residue which is suspended in 500 ml of distilled H2O, filtered through charcoal and dried. The dried residue is recrystallized from isopropanol with hot filtration to yield 3-bromo-1-ethyl-5-(4-pyrimidinyl)-2-pyridone, M.P. 195°-197° C.

Workup

  1. temperatureAfter cooling the mixture to RT
  2. customthe solvent is evaporated
  3. customleaving a solid residue which
  4. filtrationfiltered through charcoal
  5. customdried
  6. customThe dried residue is recrystallized from isopropanol with hot filtration

Sources & evidence

ORD record
ord-a18bf0d9ceb0445e93fde4b87aeb2c96
Source dataset
uspto-grants-1984_02
Patent number
US04432979

Reaction notes

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