Hydrochloric Acid → 5-[[4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]methylene]-2-(methylthio)-4(5H)-thiazolone

HRID 2226436Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2226436
[CH3:1][C:2]([C:5]1[C:10]([OH:11])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[N:8]=[C:7]([CH:16]=[C:17]2[S:21][C:20](=[S:22])[NH:19][C:18]2=[O:23])[N:6]=1)([CH3:4])[CH3:3].[CH:24](N(C(C)C)CC)(C)C.CI.Cl>O1CCCC1.C(OCC)(=O)C.[Cl-].[Na+].O>[CH3:15][C:12]([C:9]1[C:10]([OH:11])=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[N:6]=[C:7]([CH:16]=[C:17]2[S:21][C:20]([S:22][CH3:24])=[N:19][C:18]2=[O:23])[N:8]=1)([CH3:13])[CH3:14]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 539399305-[[4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]methylene]-2-thioxo-4-thiazolidinone

Produkt 1

HCID 539911875-[[4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]methylene]-2-(methylthio)-4(5H)-thiazoloneAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of 5-[[4,6-bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]methylene]-2-thioxo-4-thiazolidinone (1.00 g, 2.85 mmol) and diisopropylethylamine (0.75 g, 5.8 mmol) in tetrahydrofuran (20 mL) under nitrogen atmosphere is added methyl iodide (0.80 g, 5.6 mmol). The resulting mixture is stirred 16 hours, diluted with ethyl acetate, and with aqueous 1N hydrochloric acid solution and brine. The organic phase is dried over magnesium sulfate, concentrated, and purified by flash chromatography (SiO2, 10% ethyl acetate/hexane) followed by recrystallization from ethyl acetate and hexane to give 0.62 g (60%) of the title compound, mp 205°-208° C.

Aufarbeitung

  1. dry with materialThe organic phase is dried over magnesium sulfate
  2. concentrationconcentrated
  3. custompurified by flash chromatography (SiO2, 10% ethyl acetate/hexane)
  4. customfollowed by recrystallization from ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-ddec7a961424482f9604fb7e946c56a0
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05348957

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