Potassium Carbonate → HCID 57708305, Verbindung

HRID 404819

Reaktionsgleichung

Reaktionsgleichung von HRID 404819
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:10]=[C:11]([NH:15]C(=O)OC(C)(C)C)[CH:12]=[CH:13][CH:14]=2)[CH:3]=1.[Cl:23][C:24]1[CH:25]=[C:26]([OH:31])[CH:27]=[CH:28][C:29]=1[F:30].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Cl:23][C:24]1[CH:25]=[C:26]([CH:27]=[CH:28][C:29]=1[F:30])[O:31][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[CH:10]=2)[CH:3]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 757903-Chloro-4-fluorophenolHCID 57708283HCID 57708283, Verbindung

Produkt 1

HCID 57708305HCID 57708305, VerbindungAusbeute 45,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of tert-butyl 3-(6-chloropyrimidin-4-ylamino)phenylcarbamate (1.6 g, 5 mmol), 3-chloro-4-fluorophenol (1.4 g, 10 mmol) and potassium carbonate (1.4 g, 10 mmol) in 15 mL of DMF was heated to 120° C. for 16 h. The reaction mixture was mixed in 15 mL of water, the crude product was precipitated, filtered, purified by flash chromatography on silica gel with MeOH/DCM solvent system to afford 750 mg (45% yield) of N1-(6-(3-chloro-4-fluorophenoxy)pyrimidin-4-yl)benzene-1,3-diamine as an off-white solid. MS (m/z): MH+=331.

Aufarbeitung

  1. customthe crude product was precipitated
  2. filtrationfiltered
  3. custompurified by flash chromatography on silica gel with MeOH/DCM solvent system

Quellen und Nachweise

ORD-Eintrag
ord-3f19b32b16114826ac2328666cfec215
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748606B2

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