Hydrochloric Acid → HCID 178508398, Verbindung

HRID 28655

Reaktionsgleichung

Reaktionsgleichung von HRID 28655
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][C:9]=2[OH:15])[CH:5]=[C:4](Cl)[N:3]=1.Br[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[ClH:34].O1CCOCC1>C(#N)C.C(OCC)(=O)C>[Br:14][C:12]1[CH:11]=[CH:10][C:9]([O:15][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[C:8]([C:6]2([Cl:34])[NH:7][C:2]([NH2:1])=[N:3][CH:4]=[CH:5]2)[CH:13]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 660114-Nitrobenzyl bromideHCID 1360800122-(2-Amino-6-chloro-pyrimidin-4-yl)-4-bromo-phenol

Produkt 1

HCID 178508398HCID 178508398, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A stirred suspension of 2-(2-amino-6-chloro-pyrimidin-4-yl)-4-bromo-phenol (0.151 g, 0.50 mmol), 1-bromomethyl-4-nitro-benzene (0.218 g, 1.0 mmol), and cesium carbonate (0.325 g, 1.0 mmol) in acetonitrile (10 ml) was stirred at 80° C. for 2 hours. Filtration and concentration of the filtrate provided a crude product which was dissolved in ethyl acetate (10 ml) and stirred while a 4 M solution of hydrogen chloride in dioxane (0.50 ml, 2.0 mmol) was added. Filtration provided 6-[5-bromo-2-(4-nitro-benzyloxy)-phenyl]-6-chloro-pyrimidin-2-ylamine as hydrochloride salt (0.23 g, 96% yield).

Aufarbeitung

  1. filtrationFiltration and concentration of the filtrate
  2. customprovided a crude product which
  3. additionwas added
  4. filtrationFiltration

Quellen und Nachweise

ORD-Eintrag
ord-bdd88fb03a0342c4a0570f3bdc97a1a4
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419984B2

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