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Sodium Carbonate → HCID 71469141, Verbindung

HRID 1500792
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1500792
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][N:3]=1.[C:16]([NH:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1)(=[O:19])[CH:17]=[CH2:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[N:7]=[C:6]([C:23]2[CH:22]=[C:21]([NH:20][C:16](=[O:19])[CH:17]=[CH2:18])[CH:26]=[CH:25][CH:24]=2)[C:5]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][N:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 103213313-Acrylamidophenylboronic acidHCID 57498061HCID 57498061, Verbindung

Produkt 1

HCID 71469141HCID 71469141, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845
palladium(II) acetate
Katalysator
HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

2,4-Dichloro-N-phenylpyrimidin-5-amine (80 mg, 0.333 mmol), (3-acrylamidophenyl)-boronic acid (70.0 mg, 0.367 mmol), triphenylphosphine (3.50 mg, 0.013 mmol) and palladium acetate (1.496 mg, 6.66 μmol) were dissolved in toluene (8 mL) and 1M sodium carbonate (70.6 mg, 0.666 mmol). The reaction mixture was heated for 24 h at 90° C., allowed to cool to room temperature, and the solvent was removed in vacuo. The residue was dissolved in ethyl acetate (20 mL) and washed with water (10 mL). The organic layer was separated, the aqueous layer was extracted with ethyl acetate (20 mL), the combined organic layers were washed with brine (20 mL), and dried over Na2SO4 and concentrated. The crude material was purified by flash chromatography (20% ethyl acetate/hexane) to the title compound. 1H NMR (400 MHz, CDCl3): δ 8.55 (s, 1H), 7.89 (s, 1H), 7.74 (s, 1H), 7.66 (d, 1H, J=8.4 Hz), 7.49 (d, 1H, J=8.0 Hz), 7.38 (t, 1H, J=8.0 Hz), 7.30 (m, 2H), 7.09-7.03 (m, 3H), 6.39 (m, 1H), 6.20 (m, 1H), 6.09 (dd, 1H, J=10.4 and 17.2 Hz), 5.75 (d, 1H, J=10.4 Hz); ESI-MS: 351.1 [M+H]+.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate (20 mL)
  4. washwashed with water (10 mL)
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with ethyl acetate (20 mL)
  7. washthe combined organic layers were washed with brine (20 mL)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customThe crude material was purified by flash chromatography (20% ethyl acetate/hexane) to the title compound

Quellen und Nachweise

ORD-Eintrag
ord-fd728284ae16451d9d46411915724a2f
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09206176B2

Notizen zur Reaktion

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