Sodium hydride → HCID 18549207, compound

HRID 1266207Notes

Reaction equation

HRID 1266207 reaction equation
[CH2:1]([N:4]1[C:9](=[O:10])[CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[N:6]=[C:5]1SC)[CH:2]=[CH2:3].[F:17][C:18]([F:31])([F:30])[C:19]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:20]=1[NH2:21].[H-].[Na+].[Cl-].[NH4+]>CN(C=O)C.CCOCC>[CH2:1]([N:4]1[C:9](=[O:10])[CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[N:6]=[C:5]1[NH:21][C:20]1[CH:22]=[C:23]([C:26]([F:27])([F:28])[F:29])[CH:24]=[CH:25][C:19]=1[C:18]([F:17])([F:30])[F:31])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 7198182,5-Bis(trifluoromethyl)anilineHCID 18549204HCID 18549204, compound

Product 1

HCID 18549207HCID 18549207, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

3-Allyl-2-methylthio-6-trifluoromethyl-4(3H)-pyrimidinone (1.14 g, 4.56 mmol) was dissolved in DMF (15 ml), and 2,5-bis(trifluoromethyl)aniline (0.55 ml, 3.52 mmol) was added. Sodium hydride (60% in oil, 0.23 g, 5.75 mmol) was added with stirring under ice-cooling, followed by stirring at room temperature for 1 hour and then at 70° C. for 2.5 hours. After completion of the reaction, ether (30 ml) and saturated ammonium chloride aqueous solution (30 ml) were added to the reaction solution to separate the organic layer, and the resulting aqueous layer was extracted with ether (20 ml×2). The organic layers were combined, washed with saturated brine (20 ml×2) and then dried over anhydrous sodium sulfate. The drying agent was removed by filtration, and the resulting filtrate was concentrated under a reduced pressure. By purifying the thus obtained crude product by a silica gel column chromatography (hexane), 3-allyl-2-{2,5-bis(trifluoromethyl)phenyl}amino-6-trifluoromethyl-4(3H)pyrimidinone [Compound No. 66] was obtained as a white solid.

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature for 1 hour
  3. additionwere added to the reaction solution
  4. customto separate the organic layer
  5. extractionthe resulting aqueous layer was extracted with ether (20 ml×2)
  6. washwashed with saturated brine (20 ml×2)
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe drying agent was removed by filtration
  9. concentrationthe resulting filtrate was concentrated under a reduced pressure
  10. customBy purifying the
  11. customthus obtained crude product by a silica gel column chromatography (hexane)

Sources & evidence

ORD record
ord-5b30cc74ae2e447bb660b3c1ca18896c
Source dataset
uspto-grants-2003_04
Patent number
US06548511B1

Reaction notes

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