반응 #2373

반응 방정식

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

수율 30.4%

용매

tetrahydrofuran

n-hexane

반응 조건

후처리

1. 1
   온도the mixture is warmed to room temperature
2. 2
   추출extracted with ethyl acetate
3. 3
   세척The ethyl acetate layer is washed
4. 4
   기타dried
5. 5
   기타evaporated
6. 6
   기타to remove the solvent
7. 7
   기타The residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=2:1~1:1)
8. 8
   기타recrystallized from ethyl acetate/n-hexane

실험 절차

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.

출처