2-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)- → 3-(3-fluoro-4-(morpholinomethyl)phenyl)-2,6-dimethylpyrimidin-4(3H)-one

HRID 56083Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 56083
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH2:9][N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)[NH2:5].C[Al](C)C.[NH:20](/[C:24](/[CH3:30])=[CH:25]\[C:26](OC)=[O:27])[C:21]([CH3:23])=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([N:5]2[C:26](=[O:27])[CH:25]=[C:24]([CH3:30])[N:20]=[C:21]2[CH3:23])[CH:6]=[CH:7][C:8]=1[CH2:9][N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1

Komponenten

5

Edukt 3

HCID 57053602-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)-HCID 16682925TrimethylaluminumHCID 219550133-Fluoro-4-morpholin-4-ylmethylphenylamine

Produkt 1

HCID 729508453-(3-fluoro-4-(morpholinomethyl)phenyl)-2,6-dimethylpyrimidin-4(3H)-oneAusbeute 33,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of 3-fluoro-4-(morpholinomethyl)aniline (0.21 g, 1.00 mmol), anhydrous CH2Cl2 (10 mL) and trimethylaluminum (4.5 mL, 4.5 mmol, 1.0 M in heptane) was stirred at rt for 20 min under N2, followed by the addition of a solution of methyl 3-acetaminocrotonate (0.19 g, 1.20 mmol) in CH2Cl2 (5 mL). The reaction mixture was stirred at rt for 10 h, then quenched with saturated NH4Cl aqueous solution and extracted with CH2Cl2. The combined organic phases were washed with saturated NaHCO3 aqueous solution and brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a pale yellow solid (0.105 g, 30%). The compound was characterized by the following spectroscopic data:

Aufarbeitung

  1. stirringThe reaction mixture was stirred at rt for 10 h
  2. customquenched with saturated NH4Cl aqueous solution
  3. extractionextracted with CH2Cl2
  4. washThe combined organic phases were washed with saturated NaHCO3 aqueous solution and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-a633968430994f6a9d0cb3f46e56d76c
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434695B2

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