반응 #2385

반응 방정식

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

용매

dimethylformamide

n-hexane

반응 조건

후처리

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

실험 절차

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.

출처