Nitrogen → 3-(3-fluoro-4-(4-hydroxypiperidin-1-yl)phenyl)-2,6-dimethylpyrimidin-4(3H)-one

HRID 56154Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 56154
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]2)=[C:4]([F:15])[CH:3]=1.C[Al](C)C.N#N.[NH:22](/[C:26](/[CH3:32])=[CH:27]\[C:28](OC)=[O:29])[C:23]([CH3:25])=O>C(Cl)Cl>[F:15][C:4]1[CH:3]=[C:2]([N:1]2[C:28](=[O:29])[CH:27]=[C:26]([CH3:32])[N:22]=[C:23]2[CH3:25])[CH:7]=[CH:6][C:5]=1[N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1

Komponenten

6

Edukt 4

HCID 947NitrogenHCID 57053602-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)-HCID 16682925TrimethylaluminumHCID 289725861-(4-Amino-2-fluorophenyl)piperidin-4-ol

Produkt 1

HCID 729491183-(3-fluoro-4-(4-hydroxypiperidin-1-yl)phenyl)-2,6-dimethylpyrimidin-4(3H)-oneAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 1-(4-amino-2-fluorophenyl)piperidin-4-ol (1.68 g, 8.00 mmol) in CH2Cl2 (20 mL) was added trimethylaluminium (32 mL, 64 mmol, 2 M in heptane) carefully under N2. The mixture was stirred at rt for 30 min, followed by the addition of a solution of methyl 3-acetaminocrotonate (1.40 g, 8.90 mol) in CH2Cl2 (5 mL). The reaction mixture was stirred at rt for another 5 h, then quenched with saturated NH4Cl aqueous solution (100 mL). The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by recrystallized from EtOAc to give the title compound as a yellow solid (1.25 g, 50%). The compound was characterized by the following spectroscopic data:

Aufarbeitung

  1. stirringThe reaction mixture was stirred at rt for another 5 h
  2. customquenched with saturated NH4Cl aqueous solution (100 mL)
  3. dry with materialThe organic phase was dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified
  6. customby recrystallized from EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-cb971c3c31fc4a6289e7dd1babd85f44
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434695B2

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