Reaktion #2402

Reaktionsgleichung

ammonium chloride

5-bromo-2-chloropyrimidine

2-{6-amino-5-(4-methylphenyl)pyrimidin-4-yloxy}-ethanol

sodium hydride

→

6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-amine

Ausbeute 91.1%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe mixture is evaporated
2. 2
   Sonstigeto remove the solvent
3. 3
   FiltrationThe precipitated crystals are collected by filtration
4. 4
   Waschenwashed
5. 5
   Sonstigedried
6. 6
   SonstigeThe crude crystals are purified by silica gel column chromatography (solvent; chloroform/methanol=100:1~80:1)
7. 7
   Sonstigerecrystallized from tetrahydrofuran/diethyl ether

Vorschrift

To a solution of 2-{6-amino-5-(4-methylphenyl)pyrimidin-4-yloxy}-ethanol (7.54 g) in tetrahydrofuran (150 ml) is added sodium hydride (60% dispersion-type, 1.47 g), and thereto is added 5-bromo-2-chloropyrimidine (7.73 g), and the mixture is stirred at room temperature overnight. To the reaction solution is added saturated aqueous ammonium chloride solution, and the mixture is evaporated to remove the solvent. The precipitated crystals are collected by filtration, washed and dried. The crude crystals are purified by silica gel column chromatography (solvent; chloroform/methanol=100:1~80:1), and recrystallized from tetrahydrofuran/diethyl ether to give 6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-amine (11.27 g).

Quelle