Reaktion #2381

Reaktionsgleichung

4-tert-butyl-N-{5-(4-methylphenyl)-6-[2-(4-nitrophenoxy)ethoxy]pyrimidin-4-yl}benzenesulfonamide

→

N-{6-[2-(4-aminophenoxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide

Ausbeute 98.7%

Lösungsmittel

ethanol tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeis subjected to catalytic hydrogenation at room temperature under hydrogen atmosphere
2. 2
   Sonstigefor two hours
3. 3
   SonstigeThe catalyst is removed by filtration
4. 4
   Einengenthe filtrate is concentrated
5. 5
   SonstigeThe residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=10:1)
6. 6
   Sonstigerecrystallized from ethyl acetate/diisopropyl ether

Vorschrift

A mixture of 4-tert-butyl-N-{5-(4-methylphenyl)-6-[2-(4-nitrophenoxy)ethoxy]pyrimidin-4-yl}benzenesulfonamide (383 mg), 10% palladium-carbon (50 mg) and ethanol-tetrahydrofuran (6 ml-3 ml) is subjected to catalytic hydrogenation at room temperature under hydrogen atmosphere (1 atm) for two hours. The catalyst is removed by filtration, and the filtrate is concentrated. The residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=10:1), and recrystallized from ethyl acetate/diisopropyl ether to give N-{6-[2-(4-aminophenoxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide (358 mg).

Quelle