Dimethylformamide → HCID 18549187, compound

HRID 1266199Notes

Reaction equation

HRID 1266199 reaction equation
CN(C=O)C.[F:6][C:7]([F:20])([F:19])[C:8]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:9]=1[NH2:10].[CH3:21][N:22]1[C:27](=[O:28])[CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[N:24]=[C:23]1S(C)(=O)=O.[Cl-].[NH4+]>CCOCC.[H-].[Na+]>[F:6][C:7]([F:19])([F:20])[C:8]1[CH:14]=[CH:13][C:12]([C:15]([F:17])([F:16])[F:18])=[CH:11][C:9]=1[NH:10][C:23]1[N:22]([CH3:21])[C:27](=[O:28])[CH:26]=[C:25]([C:29]([F:32])([F:30])[F:31])[N:24]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 7198182,5-Bis(trifluoromethyl)anilineHCID 18549219HCID 18549219, compound

Product 1

HCID 18549187HCID 18549187, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 24758Sodium hydrideSolvent2×

Procedure

Sodium hydride (60% in oil, 468 mg, 17.6 mmol) was added to DMF (30 ml) solution of 2,5-bis(trifluoromethyl)aniline (3.8 g, 16.4 mmol), followed by stirring at room temperature for 30 minutes. Then, 3-methyl-2-methylsulfonyl-6-trifluoromethyl-4(3H)-pyrimidinone (3.0 g, 11.7 mmol) was added, followed by stirring for additional 4 hours. After completion of the reaction, the reaction solution was diluted with ether (20 ml), excess sodium hydride was neutralized with saturated ammonium chloride aqueous solution and then the aqueous layer was separated. After extraction of the aqueous layer with ether (20 ml×2), the organic layers were combined, washed with saturated brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure, and the resulting residue was purified by a silica gel column chromatography (hexane:ethyl acetate=20:1˜8:1) to obtain light yellow crystals of 2-{2,5-bis(trifluoromethyl)phenyl}amino-3-methyl-6-trifluoromethyl-4(3H)-pyrimidinone [Compound No. 46].

Workup

  1. stirringby stirring for additional 4 hours
  2. customAfter completion of the reaction
  3. customthe aqueous layer was separated
  4. extractionAfter extraction of the aqueous layer with ether (20 ml×2)
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under a reduced pressure
  8. customthe resulting residue was purified by a silica gel column chromatography (hexane:ethyl acetate=20:1˜8:1)

Sources & evidence

ORD record
ord-4997648fb8824e33b335e4723aeca97c
Source dataset
uspto-grants-2003_04
Patent number
US06548511B1

Reaction notes

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