Acetic Acid → HCID 55300584, compound

HRID 1910806Notes

Reaction equation

HRID 1910806 reaction equation
[C:1]([O:7]CC)(=O)[CH2:2][C:3]([CH3:5])=O.Cl.[C:11]([NH2:14])(=[NH:13])[CH3:12].[O-]CC.[Na+].C(O)(=O)C>C(O)C>[CH3:12][CH:11]1[NH:14][C:1](=[O:7])[CH2:2][C:3]([CH3:5])=[N:13]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8868Ethyl AcetoacetateHCID 67170Acetamidine monohydrochlorideHCID 2723922Sodium ethoxide

Product 1

HCID 55300584HCID 55300584, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl acetoacetate (0.8 g, 6.14 mmol) in ethanol (8 mL) was added acetamidine hydrochloride (0.6 g, 6.3 mmol) and stirred at r.t. for 10 min. A solution of sodium ethoxide [prepared from sodium (0.28 g, 12.3 mmol) and ethanol (3 mL)] was added dropwise and the whole mixture refluxed for 6 h. The reaction mass was cooled, acidified with acetic acid and concentrated under reduced pressure to give a residue which was washed twice with ethyl acetate to afford 2,6-dimethyl-2,5-dihydro-3H-pyrimidin-4-one (460 mg, 60%) as a solid.

Workup

  1. temperaturethe whole mixture refluxed for 6 h
  2. temperatureThe reaction mass was cooled
  3. concentrationconcentrated under reduced pressure
  4. customto give a residue which
  5. washwas washed twice with ethyl acetate

Sources & evidence

ORD record
ord-8a55610e98f746229543edaaec104a19
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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