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

HRID 1082306ノート

反応式

HRID 1082306 の反応式
[Br:1][C:2]1[C:3]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][CH:17]=2)(=[O:15])=[O:14])=[N:4][CH:5]=[N:6][C:7]=1[O:8][CH2:9][CH2:10][OH:11].[H-].[Na+].Cl[C:29]1[N:34]=[CH:33][C:32]([S:35][CH3:36])=[CH:31][N:30]=1.Cl.[Cl-].[NH4+]>CC(N(C)C)=O>[Br:1][C:2]1[C:3]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][CH:17]=2)(=[O:15])=[O:14])=[N:4][CH:5]=[N:6][C:7]=1[O:8][CH2:9][CH2:10][O:11][C:29]1[N:34]=[CH:33][C:32]([S:35][CH3:36])=[CH:31][N:30]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 11026374N-[5-bromo-6-(2-hydroxyethoxy)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamideHCID 219795322-Chloro-5-(methylthio)pyrimidine

生成物 1

HCID 11071742N-{5-bromo-6-[2-(5-methylthiopyrimidin-2-yloxy)ethoxy]pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide収率 83.6%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

To a solution of N-[5-bromo-6-(2-hydroxyethoxy)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide (3.10 g) in dimethylacetamide (30 ml) is added sodium hydride (60% dispersion-type, 720 mg), and the mixture is stirred at room temperature for 30 minutes. To the mixture is added 2-chloro-5-methylthiopyrimidine (1.51 g), and the mixture is stirred at room temperature overnight. The reaction solution is treated with 10% hydrochloric acid and saturated 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=10:1), and recrystallized from hexane/ethyl acetate to give N-{5-bromo-6-[2-(5-methylthiopyrimidin-2-yloxy)ethoxy]pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide (3.34 g).

後処理

  1. stirringthe mixture is stirred at room temperature overnight
  2. extractionextracted 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 silica gel column chromatography (solvent; chloroform/ethyl acetate=10:1)
  8. customrecrystallized from hexane/ethyl acetate

出典と根拠

ORDレコード
ord-7f702274c9444f4ab0d364463710523e
出典データセット
uspto-grants-1996_12
特許番号
US05589478

反応ノート

読み込み中…