Hydrochloric Acid → HCID 57839112, compound

HRID 733157Notes

Reaction equation

HRID 733157 reaction equation
[CH3:1][CH:2]([C:15](=O)[CH2:16][CH2:17][CH3:18])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1)=O.[NH2:20][C:21]([NH2:23])=[O:22].Cl>C(O)C>[CH3:1][C:2]1[C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=2)=[N:20][C:21](=[O:22])[NH:23][C:15]=1[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 1176Urea2×HCID 57839108HCID 57839108, compound

Product 1

HCID 57839112HCID 57839112, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 2-methyl-1-(3-trifluoromethylphenyl)-hexane-1,3-dione (102 mg), urea (45 mg), HCl (0.10 mL, 5M) and ethanol (4 mL) was heated at reflux for 16 h. Further urea (30 mg) and HCl (0.10 mL, 5M) were added and heating continued at reflux for 24 h. The mixture was allowed to cool and the solvent was evaporated at reduced pressure. The residue was dissolved in a mixture of ethyl acetate (10 mL) and water (10 mL), the organic layer was separated and further washed with a solution of saturated sodium carbonate (10 mL) followed by water (10 mL). The ethyl acetate extract was then dried over sodium sulphate and evaporated at reduced pressure to afford 5-methyl-6-propyl-4-(3-trifluoromethylphenyl)-1H-pyrimidin-2-one as a yellow oil (64 mg).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. temperatureheating
  4. temperatureat reflux for 24 h
  5. temperatureto cool
  6. customthe solvent was evaporated at reduced pressure
  7. dissolutionThe residue was dissolved in a mixture of ethyl acetate (10 mL) and water (10 mL)
  8. customthe organic layer was separated
  9. washfurther washed with a solution of saturated sodium carbonate (10 mL)
  10. extractionThe ethyl acetate extract
  11. dry with materialwas then dried over sodium sulphate
  12. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-4e26d75e85a743c5beb39cb3b7bd767f
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

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