Reaktion #1095858

Reaktionsgleichung

4-(2-butynyloxy)-5,6-dichloropyrimidine

3,5-dimethylpiperidine

→

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

Ausbeute 88.7%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

Into 3 ml of ethanol was resolved 0.3 g of 4-(2-butynyloxy)-5,6-dichloropyrimidine, 0.47 g of 3,5-dimethylpiperidine (cis/trans=about 3/1) was added therein, and the mixture was stirred for 8 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 0.36 g of 4-(2-butynyloxy)-5-chloro-6-(3,5-dimethylpiperidino)pyrimidine (hereinafter, referred to as Compound (8)). Compound (8) had the cis/trans diastereomer originated two methyls on the piperidine ring. The ratio of the cis/trans diastereomer was about 3.6/1.

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