Reaction #1095857

Reaction equation

4-(2-butynyloxy)-6-chloropyrimidine

3,5-dimethylpiperidine

→

4-(2-butynyloxy)-6-(3,5-dimethylpiperidino)pyrimidine

Yield 103.3%

Solvents

ethanol

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   Temperatureunder reflux condition
3. 3
   Concentrationconcentrated
4. 4
   workup.ADDITIONInto the residue was added a saturated ammonium chloride aqueous solution
5. 5
   Extractionthe mixture was extracted with tert-butyl methyl ether three times
6. 6
   WashThe organic layers were washed with a saturated sodium chloride aqueous solution
7. 7
   Dryingdried over anhydrous magnesium sulfate
8. 8
   Concentrationconcentrated

Procedure

Into 3 ml of ethanol was resolved 0.3 g of 4-(2-butynyloxy)-6-chloropyrimidine, 0.56 g of 3,5-dimethylpiperidine (cis/trans=about 3/1) was added therein, and the mixture was stirred for 10 hours under reflux condition. The reaction mixture was cooled to near room temperature, and concentrated. Into the residue was added a saturated ammonium chloride aqueous solution, 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 0.44 g of 4-(2-butynyloxy)-6-(3,5-dimethylpiperidino)pyrimidine (hereinafter, referred to as Compound (7)). Compound (7) had the cis/trans diastereomer originated two methyls on the piperidine ring. The ratio of the cis/trans diastereomer was about 3.1/1.

Source