Potassium Carbonate → (4-Benzyl-pyrimidin-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine

HRID 1855326Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1855326
C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.[CH3:26][O:27][C:28]1[CH:29]=[C:30]([NH2:40])[CH:31]=[CH:32][C:33]=1[N:34]1[CH:38]=[C:37]([CH3:39])[N:36]=[CH:35]1.[CH2:41]([C:48]1[CH:53]=[CH:52][N:51]=[C:50](Cl)[N:49]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:41]([C:48]1[CH:53]=[CH:52][N:51]=[C:50]([NH:40][C:30]2[CH:31]=[CH:32][C:33]([N:34]3[CH:38]=[C:37]([CH3:39])[N:36]=[CH:35]3)=[C:28]([O:27][CH3:26])[CH:29]=2)[N:49]=1)[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 183533314-Benzyl-2-chloro-pyrimidineHCID 454801813-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline

Produkt 1

HCID 44192500(4-Benzyl-pyrimidin-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amineAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Palladium acetate (2.7 mg, 0.012 mmol) and 2-(dicyclohexylphosphino)-biphenyl (8.7 mg, 0.024 mmol) were dissolved under an atmosphere of nitrogen in dioxane (1 mL) and stirred for 10 min at 20° C. This solution was added at 20° C. under an atmosphere of nitrogen to a microwave flask containing 3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamine (61 mg, 0.3 mmol), 4-benzyl-2-chloro-pyrimidine (68 mg, 0.3 mmol) and potassium carbonate (829 mg, 6.0 mmol). The mixture was diluted with dioxane (1.7 mL) and heated for 30 min to 200° C. in a microwave oven. The reaction was poured onto water and extracted twice with ethyl acetate. The combined organic solutions were washed with brine, dried over sodium sulfate, filtered and the residue was purified by column chromatography on silica gel using dichloromethane/methanol (19:1 v/v) as eluent to yield the title compound (50 mg, 45%) as a yellow solid.

Aufarbeitung

  1. additionThis solution was added at 20° C. under an atmosphere of nitrogen to a microwave flask
  2. temperatureheated for 30 min to 200° C. in a microwave oven
  3. additionThe reaction was poured onto water
  4. extractionextracted twice with ethyl acetate
  5. washThe combined organic solutions were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-c05ecf80ad3e4fd68661f3a294d171ce
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962834B2

Notizen zur Reaktion

Wird geladen…