Sodium Carbonate → 3-(2,3-dihydrobenzofuran-5-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 239636

Reaktionsgleichung

Reaktionsgleichung von HRID 239636
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.[O:12]1[C:16]2[CH:17]=[CH:18][C:19](B(O)O)=[CH:20][C:15]=2[CH2:14][CH2:13]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C(O)C.O>[O:12]1[C:16]2[CH:17]=[CH:18][C:19]([C:2]3[C:10]4[C:5](=[N:6][CH:7]=[N:8][C:9]=4[NH2:11])[NH:4][N:3]=3)=[CH:20][C:15]=2[CH2:14][CH2:13]1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 2773380(2,3-Dihydro-1-benzofuran-5-yl)boronic acidHCID 178508725HCID 178508725, Verbindung

Produkt 1

HCID 1785087033-(2,3-dihydrobenzofuran-5-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.70 g, 2.68 mmoles) in DMF (10 ml), ethanol (6 ml) and water (6 ml), 2,3-dihydrobenzofuran-5-boronic acid (0.527 g, 3.21 mmoles) and sodium carbonate (0.852 g, 8.04 mmoles) were added and the system is degassed for 30 min. Tetrakistriphenylphosphine Palladium (0.610 g, 0.528 mmoles) was added under nitrogen atmosphere and heated to 80° C. After 12 h, the reaction mixture was celite filtered, concentrated and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by column chromatography with methanol: dichloromethane to afford the title compound as brown solid (0.198 g, 29% yield1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 13.42(s,1H), 8.18(s,1H), 7.48(s,1H), 7.36(d, J=8.1 Hz, 1H), 6.90(d, J=8.2 Hz, 1H), 4.61(d, J=8.7 Hz, 2H),3.27(d, J=8.7 Hz, 2H).

Aufarbeitung

  1. customthe system is degassed for 30 min
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography with methanol

Quellen und Nachweise

ORD-Eintrag
ord-055b622c187c4cc18ec3cdbaa6446188
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642607B2

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