Reaction #68839

Reaction equation

cyclobutanol

5-bromo-2-chloropyrimidine

NaH

→

5-Bromo-2-cyclobutoxy-pyrimidine

Solvents

1,4-dioxane

Conditions

Workup

1. 1
   OtherAfter removing of the cooling bath the reaction mixture
2. 2
   OtherThe reaction is quenched by the addition of water and sat. aq. NaHCO3 solution
3. 3
   OtherThe 1,4-dioxane is removed in vacuo
4. 4
   Extractionthe aq. residue is extracted with DCM
5. 5
   Washwashed with water
6. 6
   Dryingdried with MgSO4
7. 7
   OtherThe solvent is removed under reduced pressure
8. 8
   OtherThe crude product is used without further purification

Procedure

2.42 mL (31.0 mmol) cyclobutanol and 3.00 g (15.5 mmol) 5-bromo-2-chloropyrimidine are added to 40 mL 1,4-dioxane and cooled down to 0° C. Then the reaction mixture is charged with 1.86 g (46.5 mmol) NaH. After removing of the cooling bath the reaction mixture is stirred at r.t. for 1 h. The reaction is quenched by the addition of water and sat. aq. NaHCO3 solution. The 1,4-dioxane is removed in vacuo and the aq. residue is extracted with DCM. The org. phases are combined, washed with water and dried with MgSO4. The solvent is removed under reduced pressure. The crude product is used without further purification.

Source