Dimethylformamide → HCID 18549201, compound

HRID 1266202Notes

Reaction equation

HRID 1266202 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].[CH2:21]([N:25]1[C:30](=[O:31])[CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[N:27]=[C:26]1S(C)(=O)=O)[CH:22]([CH3:24])[CH3:23].[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:26]1[N:25]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:30](=[O:31])[CH:29]=[C:28]([C:32]([F:35])([F:33])[F:34])[N:27]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 7198182,5-Bis(trifluoromethyl)anilineHCID 18549185HCID 18549185, compound

Product 1

HCID 18549201HCID 18549201, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 24758Sodium hydrideSolvent2×

Procedure

Sodium hydride (60% in oil, 1.01 g, 15.2 mmol) was added to DMF (30 ml) solution of 2,5-bis(trifluoromethyl)aniline (3.2 g, 14.1 mmol), followed by stirring at room temperature for 30 minutes. Then, 3-isobutyl-2-methylsulfonyl-6-trifluoromethyl-4(3H)-pyrimidinone (3.0 g, 11.7 mmol) was added, followed by further stirring for 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 (20 ml), 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 (10 ml), and then dried over anhydrous sodium sulfate. The drying agent was removed by filtration, and the solvent was evaporated from the resulting filtrate under a reduced pressure. By purifying the thus obtained crude product by a silica gel column chromatography (hexane:ethyl acetate=20:1), 2-{2,5-bis(trifluoromethyl)phenyl}amino-3-isobutyl-6-trifluoromethyl-4(3H)-pyrimidinone [Compound No. 56] was obtained as colorless crystals.

Workup

  1. stirringby further stirring for 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 (10 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe drying agent was removed by filtration
  8. customthe solvent was evaporated from the resulting filtrate under a reduced pressure
  9. customBy purifying the
  10. customthus obtained crude product by a silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-15ee8fb443b044a5a2b957e846f9462a
Source dataset
uspto-grants-2003_04
Patent number
US06548511B1

Reaction notes

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