Réaction #67072

Équation de réaction

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

Solvants

water

Conditions de réaction

Traitement

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
   LavageThe organic layer was washed with water and saturated brine
5. 5
   Séchagedried over anhydrous magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated
8. 8
   AutreThe obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate)

Mode opératoire

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