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

HRID 2252724Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2252724
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][S:9]([CH2:12][CH2:13][CH3:14])(=[O:11])=[O:10])[C:3]=1[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1.CC(C)([O-])C.[K+].[CH2:28]([OH:31])[CH2:29][OH:30]>>[OH:30][CH2:29][CH2:28][O:31][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][S:9]([CH2:12][CH2:13][CH3:14])(=[O:11])=[O:10])[C:3]=1[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1

Komponenten

4

Edukt 3

HCID 174Ethylene GlycolHCID 23665647Potassium tert-butoxideHCID 86597589n-Propanesulfonic acid (6-chloro-5-p-tolyl-pyrimidin-4-yl)-amide

Produkt 1

HCID 86597591n-Propanesulfonic acid [6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

n-Propanesulfonic acid (6-chloro-5-p-tolyl-pyrimidin-4-yl)-amide (489 mg) was added to a solution of potassium tert.-butoxide (900 mg) in ethylene glycol (10 ml). The solution was 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 n-propanesulfonic acid [6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide (390 mg) as a white powder. LC-MS: tR: 3.76, [M+H]+: 352.13.

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-d9fdfac0fff545edaccfe4631d8da53c
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07323465B2

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