Reaktion #2366

Reaktionsgleichung

4-tert-butyl-N-{6-(2-hydroxyethoxy)-5-(3-methoxyphenoxy)pyrimidin-4-yl}benzenesulfonamide

sodium hydride

ammonium chloride

5-bromo-2-chloropyrimidine

→

N-[-6-{2-(5-bromopyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide

Ausbeute 84.1%

Lösungsmittel

dimethylacetamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture is stirred at room temperature for 18 hours
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   WaschenThe ethyl acetate layer is washed
4. 4
   Sonstigedried
5. 5
   Sonstigeevaporated
6. 6
   Sonstigeto remove the solvent
7. 7
   SonstigeThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol=40:1)
8. 8
   Sonstigeto give crude crystals, which
9. 9
   Sonstigeare recrystallized from ethyl acetate/diisopropyl ether

Vorschrift

To a solution of 4-tert-butyl-N-{6-(2-hydroxyethoxy)-5-(3-methoxyphenoxy)pyrimidin-4-yl}benzenesulfonamide (250 mg) in dimethylacetamide (5 ml) is added sodium hydride (60% dispersion-type, 64 mg) at room temperature, and the mixture is stirred for 20 minutes. To the reaction solution is added 5-bromo-2-chloropyrimidine (133 mg), and the mixture is stirred at room temperature for 18 hours. The reaction solution is poured into ice-water, and the mixture is neutralized with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform/methanol=40:1) to give crude crystals, which are recrystallized from ethyl acetate/diisopropyl ether to give N-[-6-{2-(5-bromopyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide (280 mg) as crystals.

Quelle