4-Chloropyrimidine → N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-4-(4-pyrimidinylthio)butyramide

HRID 52122

Reaktionsgleichung

Reaktionsgleichung von HRID 52122
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([O:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][NH:19][C:20](=[O:28])[CH2:21][CH2:22][CH2:23][S:24][C:25](=O)[CH3:26])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[O-].[Na+].Cl[C:33]1C=C[N:36]=[CH:35][N:34]=1>CO>[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([O:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][NH:19][C:20](=[O:28])[CH2:21][CH2:22][CH2:23][S:24][C:25]3[CH:26]=[CH:33][N:34]=[CH:35][N:36]=3)[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 6428344-ChloropyrimidineHCID 10942334Sodium MethoxideHCID 86750623N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-4-(acetylthio)butyramide

Produkt 1

HCID 67725816N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-4-(4-pyrimidinylthio)butyramideAusbeute 60,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A solution of 1.00 g of N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-4-(acetylthio)butyramide [prepared as described in step (a) above] in 10 ml of methanol was added to a mixture of 0.48 g of 28% w/v methanolic sodium methoxide and 5 ml of methanol, whilst ice-cooling, and the mixture was stirred at the same temperature for 20 minutes. At the end of this time, 0.28 g of 4-chloropyrimidine was added to the mixture and the mixture was heated under reflux for 2 hours. The solvent was then removed by evaporation under reduced pressure, and water was added to the resulting residue, which was then extracted with ethyl acetate. The solvent was removed from the extract by distillation under reduced pressure, and the residue was purified by column chromatography through silica gel, using a 1:9 by volume mixture of ethanol and chloroform as the eluent, to give 0.65 g (yield 60%) of the title compound as an oil.

Aufarbeitung

  1. temperaturewhilst ice-cooling
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. customThe solvent was then removed by evaporation under reduced pressure, and water
  5. additionwas added to the resulting residue, which
  6. extractionwas then extracted with ethyl acetate
  7. customThe solvent was removed from the
  8. extractionextract by distillation under reduced pressure
  9. customthe residue was purified by column chromatography through silica gel
  10. additionby volume mixture of ethanol and chloroform as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-5fa4ab07a0464c2bb448710a3a085937
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616579

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