Reaktion #2373

Reaktionsgleichung

acetone

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

n-butyl lithium

ammonium chloride

→

4-tert-butyl-N-[6-{2-(5-(1-hydroxy-1-methylethyl)primidin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]benzenesulfonamide

Ausbeute 30.4%

Lösungsmittel

tetrahydrofuran

n-hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture is warmed to room temperature
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/ethyl acetate=2:1~1:1)
8. 8
   Sonstigerecrystallized from ethyl acetate/n-hexane

Vorschrift

To a solution of N-[6-{2-(5-bromopyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide (300 mg) in tetetrahydrofuran (10 ml) is added a 1.6M solution of n-butyl lithium in n-hexane (0.75 ml) at -78° C. The mixture is stirred at -78° C. for 5 minutes, and thereto is added a solution of acetone (58 mg) in tetrahydrofuran (1 ml), and the mixture is warmed to room temperature. The mixture is treated with 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/ethyl acetate=2:1~1:1), and recrystallized from ethyl acetate/n-hexane to give 4-tert-butyl-N-[6-{2-(5-(1-hydroxy-1-methylethyl)primidin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]benzenesulfonamide (88 mg) as crystals.

Quelle