Chloroform → HCID 178489940, Verbindung

HRID 516138Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 516138
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[NH:4][N:3]=1.[C:12]([C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH3:23])[CH:15]=1)#[CH:13].C(N(CC)CC)C.C(Cl)(Cl)Cl>CN(C=O)C.[Cu]I.O>[CH3:23][O:22][C:16]1[CH:15]=[C:14]([C:12]#[C:13][C:2]2[C:10]3[C:5](=[N:6][CH:7]=[N:8][C:9]=3[NH2:11])[NH:4][N:3]=2)[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=1

Komponenten

8

Edukt 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 46613211-Ethynyl-3,5-dimethoxybenzeneHCID 178508725HCID 178508725, Verbindung

Produkt 1

HCID 178489940HCID 178489940, VerbindungAusbeute 20,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

PdCl2(dppf)CH2Cl2 (163 mg) was added to a mixture of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (520 mg) synthesized by the method disclosed in WO 2007/126841, 1-ethynyl-3,5-dimethoxybenzene (504 mg), copper (I) iodide (57.3 mg), and triethylamine (0.56 ml) in DMF (10 ml). After nitrogen purging, the resulting mixture was stirred at 90° C. for 6 hours. Chloroform and water were added to the reaction mixture to separate the organic layer. After being washed with a saturated sodium chloride solution, the organic layer was dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. The resulting residue was purified by basic silica gel column chromatography (developing solvent: chloroform/methanol) to obtain the title compound as a dark-brown solid (120 mg). Physical properties: m/z [M+H]+ 296.0

Aufarbeitung

  1. customsynthesized by the method
  2. customto separate the organic layer
  3. washAfter being washed with a saturated sodium chloride solution
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was then distilled off under reduced pressure
  6. customThe resulting residue was purified by basic silica gel column chromatography (developing solvent: chloroform/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-8ead94e28d294fa0a4274beef02de758
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108973B2

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