Reaction #1095866

Reaction equation

pyrrolidine

N,N-dimethylformamide

4-chloro-6-(2-butynyloxy)pyrimidine

potassium carbonate

→

4-(2-butynyloxy)-6-(1-pyrrolidinyl)pyrimidine

Yield 78.4%

Solvents

ethyl acetate

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   TemperatureThe reaction mixture was cooled to near room temperature
3. 3
   Washthe mixture was washed with a saturated sodium chloride aqueous solution three times
4. 4
   DryingThe organic layers were dried over anhydrous magnesium sulfate
5. 5
   Concentrationconcentrated

Procedure

Into 2 ml of N,N-dimethylformamide was resolved 183 mg of 4-chloro-6-(2-butynyloxy)pyrimidine, 166 mg of potassium carbonate and 71 mg of pyrrolidine was added therein, and the mixture was stirred for 4 hours at 55-60° C. The reaction mixture was cooled to near room temperature, ethyl acetate was added therein, and the mixture was washed with a saturated sodium chloride aqueous solution three times. The organic layers were dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 170 mg of 4-(2-butynyloxy)-6-(1-pyrrolidinyl)pyrimidine (hereinafter, referred to as Compound (17)).

Source