Water → 5-bromo-3-(4-methoxybenzyl)pyrimidin-4(3H)-one

HRID 910610Notes

Reaction equation

HRID 910610 reaction equation
[Br:1][C:2]1[C:3](=[O:8])[NH:4][CH:5]=[N:6][CH:7]=1.[H-].[Na+].Cl[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1.O>CN(C)C=O>[Br:1][C:2]1[C:3](=[O:8])[N:4]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 882564(3H)-Pyrimidinone, 5-bromo-

Product 1

HCID 575841305-bromo-3-(4-methoxybenzyl)pyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Bromopyrimidin-4(3H)-one (459 mg) was dissolved in N,N-dimethylformamide (13 mL), then with cooling with ice, sodium hydride (55%, 137 mg) was added, followed by stirring at the same temperature for 30 minutes. Then, 1-(chloromethyl)-4-methoxybenzene (392 μL) was added, followed by stirring at room temperature for 15 hours. Water was added to the reaction mixture, followed by extraction with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 2:1) to obtain 5-bromo-3-(4-methoxybenzyl)pyrimidin-4(3H)-one (382 mg) as a white solid.

Workup

  1. additionwas added
  2. stirringby stirring at room temperature for 15 hours
  3. extractionfollowed by extraction with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 2:1)

Sources & evidence

ORD record
ord-8e4892decde845ecb2eceb4192b6efe4
Source dataset
uspto-grants-2011_09
Patent number
US08022208B2

Reaction notes

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