HCID 58446972, Verbindung → HCID 58446997, Verbindung

HRID 1045774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1045774
[Br:1][C:2]1[C:3]([N:21]=[CH:22][NH:23]O)=[N:4][C:5]([N:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)=[N:6][CH:7]=1>[OH-].[K+]>[Br:1][C:2]1[C:3]2[N:4]([N:23]=[CH:22][N:21]=2)[C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1

Komponenten

3

Edukt 1

HCID 58446972HCID 58446972, Verbindung

Produkt 1

HCID 58446997HCID 58446997, VerbindungAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14797Potassium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A 100 mL round bottom flask was charged with tert-butyl 4-(5-bromo-4-(((hydroxyamino)methylene)amino)pyrimidin-2-yl)piperazine-1-carboxylate (1.1 g) and polyphosphoric acid (20 g). The resulting mixture was stirred at 100° C. overnight. Work-up: the reaction mixture was carefully diluted with saturated aqueous KOH (300 mL) and then extracted with CH2Cl2 (100 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel to afford 0.3 g (39%) of the product as a white solid. MS m/z: 283 (M+H+).

Aufarbeitung

  1. extractionextracted with CH2Cl2 (100 mL×3)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-65e29874661e4830b05b7ac650b65b14
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569300B2

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