Ethyl benzoylacetate → 2-Methyl-6-phenyl-4-pyrimidinol

HRID 2063598Notes

Reaction equation

HRID 2063598 reaction equation
[O-]CC.[Na+].CCO[C:8]([CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O)=[O:9].Cl.[C:20]([NH2:23])(=[NH:22])[CH3:21]>>[CH3:21][C:20]1[NH:23][C:8](=[O:9])[CH:10]=[C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:22]=1

Participants

4

Reactant 3

HCID 7170Ethyl benzoylacetateHCID 67170Acetamidine monohydrochlorideHCID 2723922Sodium ethoxide

Product 1

HCID 1354430772-Methyl-6-phenyl-4-pyrimidinolYield 21%

Procedure

To a freshly prepared solution of sodium ethoxide (18 g of sodium metal was dissolved in 1 L of ethanol), was added ethyl benzoyl acetate (75 g, 0.39 mol) and the mixture was stirred at room temperature for 30 min. To this was added acetamidine hydrochloride (37 g, 0.39 mol) in portions and the mixture was refluxed for 24 h under nitrogen. The reaction mixture was cooled and excess ethanol was removed under vacuum. The residue was acidified to pH=4 with 1.5N HCl and the precipitate was filtered and dried under suction to afford 15 g (21%) of the titled compound as a white solid.

Workup

  1. temperaturethe mixture was refluxed for 24 h under nitrogen
  2. temperatureThe reaction mixture was cooled
  3. customexcess ethanol was removed under vacuum
  4. filtrationthe precipitate was filtered
  5. customdried under suction

Sources & evidence

ORD record
ord-5ad7c666c69b4af6b928f15cb9173311
Source dataset
uspto-grants-2012_10
Patent number
US08288398B2

Reaction notes

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