Potassium Carbonate → HCID 15729187, Verbindung

HRID 2380626

Reaktionsgleichung

Reaktionsgleichung von HRID 2380626
Cl.[NH2:2][C:3]1[S:4][C:5](Br)=[CH:6][N:7]=1.[NH2:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([SH:16])[N:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:2][C:3]1[S:4][C:5]([S:16][C:12]2[N:11]=[C:10]([NH2:9])[CH:15]=[CH:14][N:13]=2)=[CH:6][N:7]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 221703925-Bromo-1,3-thiazol-2-amine--hydrogen chloride (1/1)HCID 178507909HCID 178507909, Verbindung

Produkt 1

HCID 15729187HCID 15729187, VerbindungAusbeute 55,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 2-amino-5-bromothiazole hydrochloride (2.2 g), 4-amino-2-mercaptopyrimidine (2.2 g) and potassium carbonate (6.5 g) in N,N-dimethylformamide (100 ml) was heated at 90° C. for 2.5 hours with stirring. The reaction mixture was concentrated under reduced pressure and water was added to this residue. The solution was extracted with a mixture of tetrahydrofuran and ethyl acetate (1:1), washed with aqueous saturated sodium chloride and dried over magnesium sulfate. The solvent was concentrated under reduced pressure to give solid. The solid was subjected to column chromatography on silica gel (silica gel 60, 70-230 mesh; Merck: 250 g) and eluted with a mixture of chloroform and methanol (10:1). The fractions containing the objective compound were combined and concentrated under reduced pressure to give solid. The solid was triturated with ethanol to give 2-amino-5-(4-aminopyrimidin-2-ylthio)thiazole (1.25 g, yield: 55.6%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure and water
  2. additionwas added to this residue
  3. extractionThe solution was extracted with a mixture of tetrahydrofuran and ethyl acetate (1:1)
  4. washwashed with aqueous saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe solvent was concentrated under reduced pressure
  7. customto give solid
  8. washeluted with a mixture of chloroform and methanol (10:1)
  9. additionThe fractions containing the objective compound
  10. concentrationconcentrated under reduced pressure
  11. customto give solid
  12. customThe solid was triturated with ethanol

Quellen und Nachweise

ORD-Eintrag
ord-2554a99343cc417084acf99b42b06ec0
Quelldatensatz
uspto-grants-1994_11
Patentnummer
US05369107

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