Potassium Carbonate → 2-Acetylamino-5-(4-aminopyrimidin-2-ylthio)thiazole

HRID 2380639

Reaktionsgleichung

Reaktionsgleichung von HRID 2380639
[C:1]([NH:4][C:5]1[S:6][C:7](Br)=[CH:8][N:9]=1)(=[O:3])[CH3:2].[NH2:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([SH:18])[N:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([NH:4][C:5]1[S:6][C:7]([S:18][C:14]2[N:13]=[C:12]([NH2:11])[CH:17]=[CH:16][N:15]=2)=[CH:8][N:9]=1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 3502602-Acetamido-5-bromo-1,3-thiazoleHCID 178507909HCID 178507909, Verbindung

Produkt 1

HCID 157292012-Acetylamino-5-(4-aminopyrimidin-2-ylthio)thiazoleAusbeute 48,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 2-acetylamino-5-bromothiazole (2.2 g), 4-amino-2-mercaptopyrimidine (1.3 g) and potassium carbonate (2.0 g) in N,N-dimethylformamide (50 ml) was heated at 90° C. for 2 hours with stirring. The reaction mixture was concentrated under reduced pressure and the residue was triturated with water. The precipitation was collected by filtration, washed with water and dried in vacuo to give solid. The solid was subjected to column chromatography on silica gel (silica gel 60, 70-230 mesh; Merck: 200 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 no give 2-acetylamino-5-(4-aminopyrimidin-2-ylthio)thiazole (1.3 g, yield: 48.7%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was triturated with water
  3. customThe precipitation
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried in vacuo
  7. customto give solid
  8. washeluted with a mixture of chloroform and methanol (10:1)
  9. additionThe fractions containing the objective compound

Quellen und Nachweise

ORD-Eintrag
ord-ed4f17d1aee6417191d176c210e795e9
Quelldatensatz
uspto-grants-1994_11
Patentnummer
US05369107

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