Reaction #2418

Reaction equation

2-chloro-5-hydroxypyrimidine

3-chloromethylthiophene

potassium carbonate

dimethylformamide

→

2-chloro-5-(3-thienylmethoxy)pyrimidine

Yield 99.3%

Solvents

water

Conditions

Workup

1. 1
   Extractionextracted with ethyl acetate
2. 2
   WashThe organic layer is washed with water and saturated brine
3. 3
   Otherdried
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   OtherThe residue is purified by silica gel column chromatography (solvent; n-hexane/ethyl acetate=20:1→20:3)
6. 6
   Otherevaporated
7. 7
   Otherto remove the solvent

Procedure

A mixture of 2-chloro-5-hydroxypyrimidine (200 mg), 3-chloromethylthiophene (610 mg), potassium carbonate (635 mg) and dimethylformamide (3 ml) is stirred at 50° C. for one hour. After the reaction is complete, to the reaction mixture is added water, and extracted with ethyl acetate. The organic layer is washed with water and saturated brine, dried, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; n-hexane/ethyl acetate=20:1→20:3), and evaporated to remove the solvent to give 2-chloro-5-(3-thienylmethoxy)pyrimidine (345 mg) as colorless needles.

Source