Reacción #2385

Ecuación de reacción

ammonium chloride

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

n-butyl lithium

tetrahydrofuran

hydrochloric acid

→

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

Disolventes

dimethylformamide

n-hexane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe reaction solution is reacted at the same temperature for 15 minutes
2. 2
   Extracciónextracted with ethyl acetate
3. 3
   LavadoThe ethyl acetate layer is washed
4. 4
   Otrodried
5. 5
   Otrothe residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=100:1~30:1)
6. 6
   Otrorecrystallized from diisopropyl ether

Procedimiento

To a solution of N-[6-{2-(5-bromopyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide (700 mg) in tetrahydrofuran (15 ml) is added dropwise a 1.6M solution of n-butyl lithium in n-hexane (1.46 ml) at -78° C. The mixture is stirred at -78° C. for 15 minutes, and thereto is added dimethylformamide (0.28 ml), and the reaction solution is reacted at the same temperature for 15 minutes. The solution is treated with aqueous ammonium chloride solution, and acidified with 10% hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and the residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=100:1~30:1), and recrystallized from diisopropyl ether to give 4-tert-butyl-N-[6-{2-(5-formylpyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]benzenesulfonamide (198 mg) as crystals.

Fuente