2,4-Dichloropyrimidine → 2-Chloro-4-ethoxypyrimidine

HRID 386095Notes

Reaction equation

HRID 386095 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH3:9][CH2:10][O-:11].[Na+]>CCO>[Cl:1][C:2]1[N:7]=[C:6]([O:11][CH2:10][CH3:9])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 775312,4-DichloropyrimidineHCID 2723922Sodium ethoxide

Product 1

HCID 47372802-Chloro-4-ethoxypyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 2,4-dichloropyrimidine (20 g, 0.13 mmol) in 240 mL of anhydrous EtOH was added slowly 1M NaOEt in EtOH over 2 hrs at −3° C. under nitrogen atmosphere. The resulting mixture was stirred at room temperature for 1 hour. The organic solvent was evaporated in vacuo and the residue was partioned between water and Et2O. The aqueous phase was extracted with Et2O and the combined organic phases were washed with brine, dried over Na2SO4, filtered, and concentrated to give the title compound.

Workup

  1. customThe organic solvent was evaporated in vacuo
  2. extractionThe aqueous phase was extracted with Et2O
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a96d0a4658fe489e8b989c0333ca16a1
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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