Reaction #2402

Reaction equation

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

Yield 91.1%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Otherthe mixture is evaporated
2. 2
   Otherto remove the solvent
3. 3
   FiltrationThe precipitated crystals are collected by filtration
4. 4
   Washwashed
5. 5
   Otherdried
6. 6
   OtherThe crude crystals are purified by silica gel column chromatography (solvent; chloroform/methanol=100:1~80:1)
7. 7
   Otherrecrystallized from tetrahydrofuran/diethyl ether

Procedure

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).

Source