Ethanol → 1-ethyl-4,6-dimethyl-2(1H)-pyrimidinone

HRID 1076829

Reaction equation

HRID 1076829 reaction equation
[C:1]([CH2:4][C:5](=O)[CH3:6])(=O)[CH3:2].[CH2:8]([NH:10][C:11]([NH2:13])=[O:12])[CH3:9].C(O)C.S(=O)(=O)(O)O>CCOCC>[CH2:8]([N:10]1[C:1]([CH3:2])=[CH:4][C:5]([CH3:6])=[N:13][C:11]1=[O:12])[CH3:9]

Participants

6

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 12254EthylureaHCID 31261Acetylacetone

Product 1

HCID 17114931-ethyl-4,6-dimethyl-2(1H)-pyrimidinone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Acetylacetone (9.0 g., 0.09 moles) and ethylurea (7.13 g., 0.081 moles) are dissolved in 30 ml. ethanol. The solution is cooled in an ice-water bath while 30 g. of cold concentrated sulfuric acid is added. The resulting yellow solution is stored at room temperature for 10 days and diluted with a large volume of ether. The ether-ethanol mixture is decanted from the thick syrupy residue which is washed with additional fresh ether. The residue is made basic with 2.5 N sodium hydroxide and extracted throughly with methylene chloride. The organic extracts are dried over sodium sulfate, treated with charcoal, filtered, and evaporated under vacuum affording 1-ethyl-4,6-dimethyl-2(1H)-pyrimidinone as a tan solid (7.6 g., 62%).

Workup

  1. temperatureThe solution is cooled in an ice-water bath while 30 g
  2. customThe ether-ethanol mixture is decanted from the thick syrupy residue which
  3. washis washed with additional fresh ether
  4. extractionextracted throughly with methylene chloride
  5. dry with materialThe organic extracts are dried over sodium sulfate
  6. additiontreated with charcoal
  7. filtrationfiltered
  8. customevaporated under vacuum

Sources & evidence

ORD record
ord-a80bc0d08b8e4c15af9abe6049989d76
Source dataset
uspto-grants-1976_05
Patent number
US03957997

Linked notes

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