Hydrochloric Acid → 5-Ethyl-1-(4-hydroxybutyl)-6-(phenylselenenyl)-2-thiouracil

HRID 1419782

Reaktionsgleichung

Reaktionsgleichung von HRID 1419782
C([O:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C:16](S(C)=O)=[C:15]([CH2:20][CH3:21])[C:13](=[O:14])[NH:12][C:10]1=[S:11])(=O)C.[C:22]1([SeH:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[OH-].[Na+].Cl>CCO>[CH2:20]([C:15]1[C:13](=[O:14])[NH:12][C:10](=[S:11])[N:9]([CH2:8][CH2:7][CH2:6][CH2:5][OH:4])[C:16]=1[Se:28][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:21]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69530BenzeneselenolHCID 107116471-(4-Acetoxybutyl)-5-ethyl-6-(methylsulfinyl)-2-thiouracil

Produkt 1

HCID 108099705-Ethyl-1-(4-hydroxybutyl)-6-(phenylselenenyl)-2-thiouracilAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

To a stirred suspension of 1-(4-acetoxybutyl)-5-ethyl-6-(methylsulfinyl)-2-thiouracil (0.33 g, 1.00 mmol) and benzeneselenol (0.11 mL, 1.04 mmol) in EtOH (5 mL) was added 1N methanolic NaOH solution (3.00 mL) at room temperature under a nitrogen atmosphere. After the mixture was stirred for 2 h, 3N HCl in EtOH (1.00 mL) was added and the reaction mixture was evaporated to dryness. The residue was purified by flash column chromatography on silica gel with MeOH-CHCl3 (5:95) as eluent to give 0.23 g of the titled compound.

Aufarbeitung

  1. customthe reaction mixture was evaporated to dryness
  2. customThe residue was purified by flash column chromatography on silica gel with MeOH-CHCl3 (5:95) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-fed9db3e1c834c9f85c394e16a6478ac
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05889013

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