Acetamidine monohydrochloride → Ethyl 2,4-dimethylpyrimidine-5-carboxylate

HRID 1268744Notes

Reaction equation

HRID 1268744 reaction equation
Cl.[C:2]([NH2:5])(=[NH:4])[CH3:3].[O-]CC.[Na+].C(O)C.[C:13]([C:16](=[CH:22]N(C)C)[C:17]([O:19][CH2:20][CH3:21])=[O:18])(=O)[CH3:14]>>[CH3:3][C:2]1[N:5]=[C:13]([CH3:14])[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:22][N:4]=1

Participants

4

Reactant 3

HCID 67170Acetamidine monohydrochlorideHCID 3806790Ethyl 2-acetyl-3-(dimethylamino)acrylateHCID 23706232Ethanol sodium ethoxide

Product 1

HCID 295888Ethyl 2,4-dimethylpyrimidine-5-carboxylateYield 76%

Procedure

Acetamidine hydrochloride was added to a 10% sodium ethoxide-ethanol solution (410 mL, 0.53 mol) at room temperature. Then, ethyl 2-acetyl-3-(dimethylamino)acrylate (98 g, 0.53 mol) was added to the mixture, and the mixture was heated under reflux for 24 hrs. Ethanol was evaporated under reduced pressure. Water was added to the residue and the mixture was extracted with ethyl acetate. The extract was washed with water, dried and the solvent was evaporated. The residue was distilled under reduced pressure to give the title compound (73 g, yield 76%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hrs
  3. customEthanol was evaporated under reduced pressure
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with water
  7. customdried
  8. customthe solvent was evaporated
  9. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-4a6f7c3a238d4e00a276c7f279876821
Source dataset
uspto-grants-2007_04
Patent number
US07199124B2

Reaction notes

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