Sodium Hydroxide → 5-ethyl-3-(2-oxopropyl)-2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinone

HRID 1454Notes

Reaction equation

HRID 1454 reaction equation
[CH2:1]([C:3]1[C:4](=[O:22])[N:5]([CH2:19][C:20]#[CH:21])[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:7][C:8]=1[C:9]([F:12])([F:11])[F:10])[CH3:2].[OH-:23].[Na+]>C1COCC1.C(OCC)(=O)C>[CH2:1]([C:3]1[C:4](=[O:22])[N:5]([CH2:19][C:20](=[O:23])[CH3:21])[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:7][C:8]=1[C:9]([F:12])([F:11])[F:10])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 113473105-ethyl-2-phenyl-3-propargyl-6-trifluoromethyl-4(3H)-pyrimidinone2×

Product 1

HCID 196906825-ethyl-3-(2-oxopropyl)-2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinone

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 4.83 g (15.8 mmol) of 5-ethyl-3-propargyl-2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinone (compound 46) in 50 mL of THF was added 50 mL of 10% aq NaOH. The mixture was heated at reflux for 2 h, cooled and diluted with 150 mL of ethyl acetate. The organic layer was separated, washed with 50 mL of water and 50 mL of brine and dried over MgSO4. Removal of the solvent afforded 4.74 g of 5-ethyl-3-(2-oxopropyl)-2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinone (compound 179) as a white solid. 1H-NMR (CDCl3) 1.2(3H), 2.2(3H,s), 2.7(2H,q), 4.7(2H,s), 7.45(5H,m).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. temperaturecooled
  4. customThe organic layer was separated
  5. washwashed with 50 mL of water and 50 mL of brine
  6. dry with materialdried over MgSO4
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-1591768695574e68b20ca645245f4562
Source dataset
uspto-grants-1998_03
Patent number
US05726124

Reaction notes

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