Reacción #2373

Ecuación de reacción

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

Rendimiento 30.4%

Disolventes

tetrahydrofuran

n-hexane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture is warmed to room temperature
2. 2
   Extracciónextracted with ethyl acetate
3. 3
   LavadoThe ethyl acetate layer is washed
4. 4
   Otrodried
5. 5
   Otroevaporated
6. 6
   Otroto remove the solvent
7. 7
   OtroThe residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=2:1~1:1)
8. 8
   Otrorecrystallized from ethyl acetate/n-hexane

Procedimiento

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.

Fuente