Reaction #1095885

Reaction equation

ammonium chloride

4-(2-butynyloxy)-6-chloropyrimidine

potassium carbonate

3,4-dimethylpyrrolidine hydrochloride

→

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

Yield 104.2%

Solvents

acetonitrile

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was cooled to near room temperature
2. 2
   Extractionthe mixture was extracted with tert-butyl methyl ether three times
3. 3
   WashThe organic layers were washed with a saturated sodium chloride aqueous solution
4. 4
   Dryingdried over anhydrous magnesium sulfate
5. 5
   Concentrationconcentrated

Procedure

Into 3 ml of acetonitrile were added 0.30 g of 4-(2-butynyloxy)-6-chloropyrimidine, 0.68 g of potassium carbonate and 0.33 g of 3,4-dimethylpyrrolidine hydrochloride (cis and trans diastereomer mixture), and the mixture was stirred for 4 hours at 70° C. The reaction mixture was cooled to near room temperature, a saturated ammonium chloride aqueous solution was added therein, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.42 g of 4-(2-butynyloxy)-6-(3,4-dimethylpyrrolidin-1-yl)pyrimidine (hereinafter, referred to as Compound (37)).

Source