Sodium hydride → N-{5-bromo-6-[2-(5-methylthiopyrimidin-2-yloxy)ethoxy]pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide

HRID 1082312ノート

反応式

HRID 1082312 の反応式
[Br:1][C:2]1[C:3]([NH2:20])=[N:4][CH:5]=[N:6][C:7]=1[O:8][CH2:9][CH2:10][O:11][C:12]1[N:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][N:13]=1.[H-].[Na+].[C:23]([C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24].[Cl-].[NH4+]>O1CCCC1.O.N1C=CC=CC=1>[Br:1][C:2]1[C:3]([NH:20][S:33]([C:30]2[CH:31]=[CH:32][C:27]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:28][CH:29]=2)(=[O:35])=[O:34])=[N:4][CH:5]=[N:6][C:7]=1[O:8][CH2:9][CH2:10][O:11][C:12]1[N:13]=[CH:14][C:15]([S:18][CH3:19])=[CH:16][N:17]=1

参加物

8

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 196895255-Bromo-6-[2-(5-methylthiopyrimidin-2-yloxy)ethoxy]pyrimidine-4-amine

生成物 1

HCID 11071742N-{5-bromo-6-[2-(5-methylthiopyrimidin-2-yloxy)ethoxy]pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide収率 85.5%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1049Pyridine溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 5-bromo-6-[2-(5-methylthiopyrimidin-2-yloxy)ethoxy]pyrimidine-4-amine (102 mg) in tetrahydrofuran (2 ml) is added sodium hydride (60% dispersion-type, 34 mg), and thereto is added 4-tert-butylbenzenesulfonyl chloride (198 mg). The mixture is stirred at room temperature for 20 minutes, and thereto are added a drop of pyridine and water. The mixture is stirred at room temperature for 30 minutes, and neutralized with saturated aqueous ammonium chloride solution. The mixture is extracted with ethyl acetate, and the ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is purified by preparative thin layer chromatography (solvent; chloroform/methanol=15:1), and recrystallized from hexane/ethyl acetate to give N-{5-bromo-6-[2-(5-methylthiopyrimidin-2-yloxy)ethoxy]pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide (135 mg). The physical properties thereof are the same as those of the compound obtained in Reference Example 16-(4).

後処理

  1. stirringThe mixture is stirred at room temperature for 30 minutes
  2. extractionThe mixture is extracted with ethyl acetate
  3. washthe ethyl acetate layer is washed
  4. customdried
  5. customevaporated
  6. customto remove the solvent
  7. customThe residue is purified by preparative thin layer chromatography (solvent; chloroform/methanol=15:1)
  8. customrecrystallized from hexane/ethyl acetate

出典と根拠

ORDレコード
ord-c1111c2449d44563a759643daadc5e46
出典データセット
uspto-grants-1996_12
特許番号
US05589478

反応ノート

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