Hydrochloric Acid → 3-(3-Methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 1476163Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1476163
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.[CH3:12][O:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>CN(C=O)C.C(O)C.O.ClCCl>[CH3:12][O:13][C:14]1[CH:19]=[C:18]([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:17]=[CH:16][CH:15]=1

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 178508725HCID 178508725, Verbindung

Produkt 1

HCID 1784899393-(3-Methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amineAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 3-Iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.522 g, 2.0 mmoles) in DMF (10 ml), ethanol (5 ml) and water (5 ml), 3-methoxyphenylboronic acid (0.395 g, 2.59 mmoles) and sodium carbonate (1.05 g, 10 mmoles) were added and the system is degassed for 30 min Palladium tetrakis triphenylphosphine (0.455 g, 0.39 mmoles) was added under nitrogen atmosphere and heated to 80° C. After 12 h, the reaction mixture neutralised with 1.5N HCl, 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 off-white solid (0.130 g, 27% yield). 1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 13.57(s, 1H), 8.20(s, 1H), 7.46(t, J=7.8Hz, 1H), 7.23(d, J=7.5 Hz, 1H), 7.18(d, J=2.4Hz, 1H), 7.04 (dd, J=8.0,1.8 Hz, 1H), 3.81(s, 3H).

Aufarbeitung

  1. additionwas added under nitrogen atmosphere
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography with methanol

Quellen und Nachweise

ORD-Eintrag
ord-2cf4926719944927b89dabd9eb7933eb
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09018375B2

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