Reaction #87409

Reaction equation

Water

Sodium hydride

cyclopropylmethanol

2,4-dichloro-6-[(2,2,2-trifluoroethoxy)methyl]pyrimidine

→

title compound

2-Chloro-4-(cyclopropylmethoxy)-6-[(2,2,2-trifluoroethoxy)methyl]pyrimidine

Solvents

THF

THF

Conditions

Workup

1. 1
   workup.STIRRINGThe reaction was stirred at room temperature for 2.5 hours
2. 2
   Extractionthe mixture was extracted with ethylacetate
3. 3
   WashThe organic phase was washed with water, brine
4. 4
   Dryingdried over magnesium sulfate
5. 5
   Otherthe solvent was removed under reduced pressure
6. 6
   OtherThe residue was purified by flash chromatography on silica gel
7. 7
   Washeluting with mixtures of 0% to 10% ethyl acetate in heptanes

Procedure

Sodium hydride (19.0 mg, 0.46 mmol) was added to a solution of cyclopropylmethanol (0.037 mL, 0.46 mmol) in dry THF (1 mL) at room temperature. The mixture was stirred for 5 minutes and then a solution of 2,4-dichloro-6-[(2,2,2-trifluoroethoxy)methyl]pyrimidine (120 mg, 0.46 mmol) in dry THF (1 mL) was added. The reaction was stirred at room temperature for 2.5 hours. Water was added and the mixture was extracted with ethylacetate. The organic phase was washed with water, brine, dried over magnesium sulfate and the solvent was removed under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with mixtures of 0% to 10% ethyl acetate in heptanes to afford the title compound as a solid, 40 mg, (29%) as yellow solid.

Source