Methanol → 4,6-Dimethoxypyrimidine-5-carbaldehyde

HRID 393167

Reaction equation

HRID 393167 reaction equation
Cl[C:2]1[C:7]([CH:8]=[O:9])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[CH3:11][O-:12].[Na+].[CH3:14][OH:15]>>[CH3:11][O:12][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([O:15][CH3:14])[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 8196914,6-Dichloro-5-pyrimidinecarbaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 44366454,6-Dimethoxypyrimidine-5-carbaldehydeYield 20%

Procedure

43.6 g (246 mmol) of 4,6-dichloropyrimidine-5-carboaldehyde was dissolved in 200 ml of methanol, and 120 g (622 mmol) of 28% sodium methoxide was added under cooling with ice and then reacted for 2 hours at room temperature. After completion of the reaction, the solvent was distilled off, and an aqueous citric acid solution was added, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous sodium hydrogencarbonate solution, an aqueous citric acid solution, water and an aqueous sodium chloride solution in this order, dried and concentrated, and the obtained crude crystals were washed with isopropyl ether to obtain 8.3 g (yield: 20%) of 4,6-dimethoxypyrimidine-5-carboaldehyde.

Workup

  1. temperatureunder cooling with ice
  2. customreacted for 2 hours at room temperature
  3. customAfter completion of the reaction
  4. distillationthe solvent was distilled off
  5. additionan aqueous citric acid solution was added
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layer was washed with an aqueous sodium hydrogencarbonate solution
  8. dry with materialan aqueous citric acid solution, water and an aqueous sodium chloride solution in this order, dried
  9. concentrationconcentrated
  10. customthe obtained crude crystals
  11. washwere washed with isopropyl ether

Sources & evidence

ORD record
ord-3365243bc67640c2b8828e7859d2fbfe
Source dataset
uspto-grants-2004_10
Patent number
US06806230B1

Linked notes

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