Ethylene Glycol → Ethanesulfonic acid [6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide

HRID 2252721

Reaktionsgleichung

Reaktionsgleichung von HRID 2252721
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][S:9]([CH2:12][CH3:13])(=[O:11])=[O:10])[C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1.CC(C)([O-])C.[K+].[CH2:27]([OH:30])[CH2:28][OH:29]>>[OH:29][CH2:28][CH2:27][O:30][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][S:9]([CH2:12][CH3:13])(=[O:11])=[O:10])[C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1

Komponenten

4

Edukt 3

HCID 174Ethylene GlycolHCID 23665647Potassium tert-butoxideHCID 59645274Ethanesulfonic acid (6-chloro-5-p-tolyl-pyrimidin-4-yl)-amide

Produkt 1

HCID 59645277Ethanesulfonic acid [6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Ethanesulfonic acid (6-chloro-5-p-tolyl-pyrimidin-4-yl)-amide (363 mg) was added to a solution of potassium tert.-butoxide (427 mg) in ethylene glycol (7 ml) and stirred at 100° C. for 7 days. The reaction mixture was then poured onto ice/water and extracted with ethyl acetate. The crude product was purified by chromatography over silicagel with DCM/MeOH=9/1 to give ethanesulfonic acid [6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide (310 mg) as a white powder. LC-MS: tR: 3.47, [M+H]+: 338.13.

Aufarbeitung

  1. additionThe reaction mixture was then poured onto ice/water
  2. extractionextracted with ethyl acetate
  3. customThe crude product was purified by chromatography over silicagel with DCM/MeOH=9/1

Quellen und Nachweise

ORD-Eintrag
ord-1eec02ef45494ea5958f5f53f6737d22
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07323465B2

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