Reaction #67072

Reaction equation

bromomethyl cyclohexane

Sodium hydride

bromomethyl cyclohexane

sodium hydride

N,N-dimethylformamide

{2-[(3-chlorophenyl)amino]-4-(trifluoromethyl)pyrimidin-5-yl}methanol

→

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

Solvents

water

Conditions

Workup

1. 1
   workup.STIRRINGby stirring at room temperature for 2 hours
2. 2
   workup.STIRRINGby stirring at room temperature overnight
3. 3
   Extractionthe aqueous layer was extracted with ethyl acetate
4. 4
   WashThe organic layer was washed with water and saturated brine
5. 5
   Dryingdried over anhydrous magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated
8. 8
   OtherThe obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate)

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.

Source