Dimethylformamide → N-(3-chlorophenyl)-5-[(cyclohexylmethoxy)methyl]-4-(trifluoromethyl)pyrimidin-2-amine

HRID 38794Notes

Reaction equation

HRID 38794 reaction equation
[H-].[Na+].CN(C)C=O.[Cl:8][C:9]1[CH:10]=[C:11]([NH:15][C:16]2[N:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[C:19]([CH2:26][OH:27])=[CH:18][N:17]=2)[CH:12]=[CH:13][CH:14]=1.Br[CH2:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>O>[Cl:8][C:9]1[CH:10]=[C:11]([NH:15][C:16]2[N:21]=[C:20]([C:22]([F:24])([F:25])[F:23])[C:19]([CH2:26][O:27][CH2:29][CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:18][N:17]=2)[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydride2×HCID 137636Cyclohexane, (bromomethyl)-2×HCID 58168920[2-(3-Chlorophenylamino)-4-trifluoromethyl-pyrimidin-5-yl]-methanol

Product 1

HCID 58168816N-(3-chlorophenyl)-5-[(cyclohexylmethoxy)methyl]-4-(trifluoromethyl)pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 60% sodium hydride (26 mg) and N,N-dimethylformamide (4 mL) was added {2-[(3-chlorophenyl)amino]-4-(trifluoromethyl)pyrimidin-5-yl}methanol (200 mg), followed by stirring at room temperature for 30 minutes. Thereafter, bromomethyl cyclohexane (139 μL) was added thereto, followed by stirring at room temperature for 2 hours. 60% Sodium hydride (26 mg) and bromomethyl cyclohexane (139 μL) were added thereto again, followed by stirring at room temperature overnight. To the reaction mixture was added water and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, then dried over anhydrous magnesium sulfate, filtered, and concentrated. The obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate) to obtain N-(3-chlorophenyl)-5-[(cyclohexylmethoxy)methyl]-4-(trifluoromethyl)pyrimidin-2-amine (100 mg) as a white solid.

Workup

  1. stirringby stirring at room temperature for 2 hours
  2. stirringby stirring at room temperature overnight
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-db485af3fe1c4fd6bf55ba9958b19d9e
Source dataset
uspto-grants-2013_09
Patent number
US08524727B2

Reaction notes

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