3-Fluoro-4-morpholinoaniline → 2-((3,4-difluorophenoxy)methyl)-3-(3-fluoro-4-morpholinophenyl)-6-methyl-pyrimidin-4(3H)-one

HRID 56243

Reaktionsgleichung

Reaktionsgleichung von HRID 56243
[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.C[O:20][C:21](=O)/[CH:22]=[C:23](\[NH:25][C:26](=O)[CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([F:35])=[C:31]([F:36])[CH:30]=1)/[CH3:24]>C(Cl)Cl>[F:36][C:31]1[CH:30]=[C:29]([CH:34]=[CH:33][C:32]=1[F:35])[O:28][CH2:27][C:26]1[N:5]([C:4]2[CH:6]=[CH:7][C:8]([N:9]3[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)=[C:2]([F:1])[CH:3]=2)[C:21](=[O:20])[CH:22]=[C:23]([CH3:24])[N:25]=1

Komponenten

5

Edukt 3

HCID 14853303-Fluoro-4-morpholinoanilineHCID 16682925TrimethylaluminumHCID 90023321(Z)-methyl 3-(2-(3,4-difluorophenoxy)acetamido)but-2-enoate

Produkt 1

HCID 729492992-((3,4-difluorophenoxy)methyl)-3-(3-fluoro-4-morpholinophenyl)-6-methyl-pyrimidin-4(3H)-oneAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 3-fluoro-4-morpholinoaniline (0.39 g, 2.00 mmol) in DCM (15 mL) was added trimethylaluminium (3.5 mL, 7.0 mmol, 2 M in toluene) and the mixture was stirred at rt for 0.5 h. A solution of (Z)-methyl-3-(2-(3,4-difluorophenoxy)acetamido)but-2-enoate (0.57 g, 2.00 mmol) in DCM (5 mL) was added slowly and the resulting mixture was stirred further at rt for 12 h. The mixture was then quenched with saturated NH4Cl aqueous solution and extracted with CH2Cl2 (50 mL×2). The combined organic phases were washed with brine (100 mL), 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 brown solid (0.50 g, 58%). The compound was characterized by the following spectroscopic data:

Aufarbeitung

  1. stirringthe resulting mixture was stirred further at rt for 12 h
  2. customThe mixture was then quenched with saturated NH4Cl aqueous solution
  3. extractionextracted with CH2Cl2 (50 mL×2)
  4. washThe combined organic phases were washed with brine (100 mL)
  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-832caf4729fa4de5a129f76a30ddbb2d
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434695B2

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