Reaction #1144437

Reaction equation

chloromethyl ethyl ether

5-iodouracil

bistrimethylsilylacetamide

→

1-(ethoxy-methyl)-5-iodouracil

Yield 91.7%

Solvents

dichloromethane

Conditions

Workup

1. 1
   Otherto form a homogeneous solution
2. 2
   Temperatureheated
3. 3
   Temperatureunder reflux for 3 hours
4. 4
   OtherAfter the solvent was evaporated under reduced pressure
5. 5
   workup.ADDITIONthe residue was added with water
6. 6
   Otherto produce crystals, which
7. 7
   Filtrationwere taken by filtration
8. 8
   WashThe crystals were washed
9. 9
   Otherrecovering them
10. 10
    Temperatureby cooling
11. 11
    Filtrationfiltration

Procedure

In 50 ml of dichloromethane, 4.76 g (20 mmol) of 5-iodouracil was suspended and added with 11 ml (45 mmol) of bistrimethylsilylacetamide and stirred for 15 minutes at room temperature to form a homogeneous solution. This solution was added with 2.04 ml (22 mmol) of chloromethyl ethyl ether and 60 mg of tetra-n-butylammonium iodide and heated under reflux for 3 hours. After the solvent was evaporated under reduced pressure, the residue was added with water to produce crystals, which were taken by filtration. The crystals were washed by suspending them in hot methanol and recovering them by cooling and filtration to obtain 5.43 g of 1-(ethoxy-methyl)-5-iodouracil.

Source