Cesium carbonate → 4-(1-Ethoxyvinyl)-N-(3-methoxy-4-(6-methylpyridazin-4-yl)phenyl)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-2-amine

HRID 59097

Reaktionsgleichung

Reaktionsgleichung von HRID 59097
Cl[C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[CH2:9])[CH:5]=[C:4]([CH2:13][O:14][CH2:15][C:16]([F:19])([F:18])[F:17])[N:3]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][C:28]=1[C:29]1[CH:34]=[C:33]([CH3:35])[N:32]=[N:31][CH:30]=1)[NH2:25].C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:11]([O:10][C:8]([C:6]1[CH:5]=[C:4]([CH2:13][O:14][CH2:15][C:16]([F:19])([F:18])[F:17])[N:3]=[C:2]([NH:25][C:24]2[CH:26]=[CH:27][C:28]([C:29]3[CH:34]=[C:33]([CH3:35])[N:32]=[N:31][CH:30]=3)=[C:22]([O:21][CH3:20])[CH:23]=2)[N:7]=1)=[CH2:9])[CH3:12]

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 668590663-Methoxy-4-(6-methylpyridazin-4-yl)anilineHCID 1178207992-Chloro-4-(1-ethoxyvinyl)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine

Produkt 1

HCID 1178210484-(1-Ethoxyvinyl)-N-(3-methoxy-4-(6-methylpyridazin-4-yl)phenyl)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-2-amineAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

2-Chloro-4-(1-ethoxyvinyl)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine (0.70 g, 2.36 mmol), 3-methoxy-4-(6-methylpyridazin-4-yl)aniline (0.508 g, 2.36 mmol), cesium carbonate (1.538 g, 4.72 mmol), palladium(II) acetate (0.079 g, 0.35 mmol) and 2-(dicyclohexylphosphino)biphenyl (0.124 g, 0.35 mmol) were mixed in dioxane (16 mL). The vial was capped, evacuated and flushed with nitrogen. The reaction mixture was heated at 120° C. for 1.5 h. The mixture was filtered and the filter was washed with mixtures of methanol and DCM. The filtrate was concentrated. The residue was purified by column chromatography on silica column eluting with a gradient of methanol and DCM to give the title compound as a solid 702 mg (63%).

Aufarbeitung

  1. customThe vial was capped
  2. customevacuated
  3. customflushed with nitrogen
  4. filtrationThe mixture was filtered
  5. washthe filter was washed with mixtures of methanol and DCM
  6. concentrationThe filtrate was concentrated
  7. customThe residue was purified by column chromatography on silica column
  8. washeluting with a gradient of methanol and DCM

Quellen und Nachweise

ORD-Eintrag
ord-625d0562a5f0403d9273f1fdee12028b
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09439904B2

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