Water → 5-(2,6-Diethyl-Phenyl)-1-(4,6-Dimethyl-Pyrimidin-2-YL)-1H-Pyrrolo[2,3-c]Pyridine

HRID 472027Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 472027
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:12]=[C:13]2[CH:19]=[CH:18][NH:17][C:14]2=[CH:15][N:16]=1)[CH3:2].[H-].[Na+].Cl[C:23]1[N:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[N:24]=1.O>CN(C=O)C.CCOC(C)=O>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:12]=[C:13]2[CH:19]=[CH:18][N:17]([C:23]3[N:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[N:24]=3)[C:14]2=[CH:15][N:16]=1)[CH3:2]

Komponenten

7

Edukt 4

HCID 962WaterHCID 205502-Chloro-4,6-dimethylpyrimidineHCID 24758Sodium hydrideHCID 116732465-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine

Produkt 1

HCID 582699465-(2,6-Diethyl-Phenyl)-1-(4,6-Dimethyl-Pyrimidin-2-YL)-1H-Pyrrolo[2,3-c]Pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 5-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine (10 mg, 0.04 mmol) in DMF (0.5 mL) is added NaH (95%, 3 mg). The reaction mixture is stirred at room temperature for 30 minutes, and then 2-chloro-4,6-dimethyl-pyrimidine (17 mg, 0.12 mmol)) is added. The mixture is heated at 60° C. overnight and cooled. Water (1 mL) and EtOAc (2 mL) are added to the mixture. The organic layer is separated, washed with water once and concentrated under reduced pressure. The residue is purified by PTLC (Hexane/EtOAc 4:1) to give the titled compound. 1H NMR: (CDCl3) 10.21 (s, 1H), 8.48 (d, 1H), 7.47 (s, 1H), 7.28 (t, 1H), 7.15 (d, 2H), 6.87 (s, 1H), 6.68 (d, 1H), 2.55 (s, 6H), 2.36 (m, 4H), 1.03 (t, 6H).

Aufarbeitung

  1. temperatureThe mixture is heated at 60° C. overnight
  2. temperaturecooled
  3. customThe organic layer is separated
  4. washwashed with water once
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by PTLC (Hexane/EtOAc 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-3cb85de494f241969c696bd7123f3495
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633193B2

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