Nitrogen → 3-(3-fluoro-4-morpholinophenyl)-2,6-dimethylpyrimidin-4(3H)-one

HRID 56090

Reaktionsgleichung

Reaktionsgleichung von HRID 56090
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)[NH2:5].C[Al](C)C.N#N.[NH:21](/[C:25](/[CH3:31])=[CH:26]\[C:27](OC)=[O:28])[C:22]([CH3:24])=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([N:5]2[C:27](=[O:28])[CH:26]=[C:25]([CH3:31])[N:21]=[C:22]2[CH3:24])[CH:6]=[CH:7][C:8]=1[N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1

Komponenten

6

Edukt 4

HCID 947NitrogenHCID 14853303-Fluoro-4-morpholinoanilineHCID 57053602-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)-HCID 16682925Trimethylaluminum

Produkt 1

HCID 729482043-(3-fluoro-4-morpholinophenyl)-2,6-dimethylpyrimidin-4(3H)-oneAusbeute 67,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 3-fluoro-4-morpholinoaniline (11.0 g, 56 mmol) in CH2Cl2 (200 mL) was added trimethylaluminium (168 mL, 168 mmol, 1 M in heptane) dropwise carefully under N2. The mixture was stirred at rt for 20 min, followed by the addition of a solution of methyl 3-acetaminocrotonate (10.57 g, 67 mmol) in CH2Cl2 (30 mL). The reaction was stirred at rt for 5 h, then quenched with saturated NH4Cl aqueous solution and extracted with CH2Cl2. The combined organic phases were washed with water, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was recrystallized from EtOAc to give the title compound as a pale yellow solid (11.39 g, 67%). The compound was characterized by the following spectroscopic data:

Aufarbeitung

  1. stirringThe reaction was stirred at rt for 5 h
  2. customquenched with saturated NH4Cl aqueous solution
  3. extractionextracted with CH2Cl2
  4. washThe combined organic phases were washed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was recrystallized from EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-0c5eb14a07444697aec7fb0a52a6ebea
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434695B2

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