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

HRID 1981508Notes

Reaction equation

HRID 1981508 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-1eb83b3cdefa42a4971f091ecd8d150d
Source dataset
uspto-grants-1986_06
Patent number
US04593028

Reaction notes

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