3,5-Dimethylpiperidine → 4-(2-Butynyloxy)-5-chloro-6-(3,5-dimethylpiperidino)pyrimidine

HRID 14519

Reaktionsgleichung

Reaktionsgleichung von HRID 14519
[CH2:1]([O:5][C:6]1[C:11]([Cl:12])=[C:10](Cl)[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4].[CH3:14][CH:15]1[CH2:20][CH:19]([CH3:21])[CH2:18][NH:17][CH2:16]1>C(O)C>[CH2:1]([O:5][C:6]1[C:11]([Cl:12])=[C:10]([N:17]2[CH2:18][CH:19]([CH3:21])[CH2:20][CH:15]([CH3:14])[CH2:16]2)[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4]

Komponenten

4

Edukt 2

HCID 1182593,5-DimethylpiperidineHCID 225997514,5-Dichloro-6-(2-butynyloxy)pyrimidine

Produkt 1

HCID 578246894-(2-Butynyloxy)-5-chloro-6-(3,5-dimethylpiperidino)pyrimidineAusbeute 88,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. additionwas added
  2. temperatureunder reflux condition
  3. concentrationconcentrated
  4. additionInto the residue was added a saturated ammonium chloride aqueous solution
  5. extractionthe mixture was extracted with tert-butyl methyl ether three times
  6. washThe organic layers were washed with a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4cacccafb60d4698b87de131aa2ab9d0
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732448B2

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