Reaction #1095877

Reaction equation

3,3-dimethylpyrrolidine

N,N-dimethylformamide

4-(2-butynyloxy)-6-chloro-5-fluoropyrimidine

potassium carbonate

→

4-(2-butynyloxy)-5-fluoro-6-(3,3-dimethylpyrrolidin-1-yl)pyrimidine

Yield 31.7%

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 4 ml of N,N-dimethylformamide was resolved 0.36 g of 4-(2-butynyloxy)-6-chloro-5-fluoropyrimidine, 0.62 g of potassium carbonate and 0.25 g of 3,3-dimethylpyrrolidine was added therein, and the mixture was stirred for 6 hours at 80° 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 0.15 g of 4-(2-butynyloxy)-5-fluoro-6-(3,3-dimethylpyrrolidin-1-yl)pyrimidine (hereinafter, referred to as Compound (28)).

Source