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

HRID 2289

반응식

HRID 2289 반응식
Br[C:2]1[CH:3]=[N:4][C:5]([O:8][CH2:9][CH2:10][O:11][C:12]2[N:17]=[CH:16][N:15]=[C:14]([NH:18][S:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[C:13]=2[C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)=[N:6][CH:7]=1.C([Li])CCC.[Cl-].[NH4+].Cl.[O:47]1CCC[CH2:48]1>CCCCCC.CN(C)C=O>[C:28]([C:25]1[CH:26]=[CH:27][C:22]([S:19]([NH:18][C:14]2[C:13]([C:32]3[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=3)=[C:12]([O:11][CH2:10][CH2:9][O:8][C:5]3[N:4]=[CH:3][C:2]([CH:48]=[O:47])=[CH:7][N:6]=3)[N:17]=[CH:16][N:15]=2)(=[O:21])=[O:20])=[CH:23][CH:24]=1)([CH3:31])([CH3:30])[CH3:29]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 99385714-tert-butyl-N-{6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamideHCID 178418339Butyllithium

생성물 1

HCID 110280074-tert-butyl-N-[6-{2-(5-formylpyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]benzenesulfonamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8058Hexane용매

반응 조건

온도
-78 °C

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.

후처리

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

출처 및 근거

ORD 기록
ord-671a4344bcc6404d855dd54d549761c1
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728706

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