Reaction #1095865

Reaction equation

piperidine

N,N-dimethylformamide

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

potassium carbonate

→

4-(2-butynyloxy)-6-piperidinopyrimidine

Yield 77.1%

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 85 mg of piperidine was added therein, and the mixture was stirred for 5 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 178 mg of 4-(2-butynyloxy)-6-piperidinopyrimidine (hereinafter, referred to as Compound (16)).

Source