Reaktion #2376

Reaktionsgleichung

4-tert-butyl-N-{5-(4-methylphenyl)-6-{2-(5-nitropyridin-2-yloxy)ethoxy}pyrimidin-4-yl}benzenesulfonamide

→

N-{6-{2-(5-aminopyridin-2-yl-oxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide

Ausbeute 89.8%

Lösungsmittel

isopropanol tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe catalyst is removed by filtration
2. 2
   Einengenthe filtrate is concentrated under reduced pressure
3. 3
   SonstigeThe residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=2:1)
4. 4
   Sonstigerecrystallized from ethyl acetate/n-hexane

Vorschrift

To a solution of 4-tert-butyl-N-{5-(4-methylphenyl)-6-{2-(5-nitropyridin-2-yloxy)ethoxy}pyrimidin-4-yl}benzenesulfonamide (975 mg) in isopropanol/tetrahydrofuran (1:1) (20 ml) is added 10% palladium-carbon (200 mg), and the mixture is stirred at room temperature for 1.5 hour under hydrogen atmosphere (1 atm). The catalyst is removed by filtration, and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=2:1), and recrystallized from ethyl acetate/n-hexane to give N-{6-{2-(5-aminopyridin-2-yl-oxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide (829 mg) as crystals.

Quelle