Benzyl Chloride → 1-Benzyl-3-bromo-5-(pyrimidin-4-yl)pyridin-2(1H)-one

HRID 1388657Notes

Reaction equation

HRID 1388657 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.[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C.CO>[CH2:18]([N:7]1[CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][N:12]=2)[CH:10]=[C:5]([Br:4])[C:6]1=[O:17])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 10942334Sodium MethoxideHCID 132766783-Bromo-5-(pyrimidin-4-yl)pyridin-2(1H)-one

Product 1

HCID 136450971-Benzyl-3-bromo-5-(pyrimidin-4-yl)pyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

A solution of sodium methoxide (1.85 g) in 100 ml DMF and 30 ml MeOH is added to a stirred suspension of 3-bromo-5-(4-pyrimidinyl)-2(1H)-pyridone in 100 ml DMF. Benzyl chloride (3.9 ml) is added to the reaction mixture, and the mixture is heated to 70° C. for 2 hours and allowed to cool to RT overnight. The reaction mixture is filtered and the solvent evaporated in vacuo. The residue is suspended in H2O, filtered and dried. The resultant solid is dissolved in hot isopropanol, filtered through charcoal and recrystallized, yielding 1-benzyl-3-bromo-5-(4-pyrimidinyl)-2-pyridone, M.P. 189°-191.5° C.

Workup

  1. temperatureto cool to RT overnight
  2. filtrationThe reaction mixture is filtered
  3. customthe solvent evaporated in vacuo
  4. filtrationfiltered
  5. customdried
  6. dissolutionThe resultant solid is dissolved in hot isopropanol
  7. filtrationfiltered through charcoal
  8. customrecrystallized

Sources & evidence

ORD record
ord-859d7e3577e3431992682983899ed108
Source dataset
uspto-grants-1984_02
Patent number
US04432979

Reaction notes

Loading…