Hexane → HCID 66977004, Verbindung

HRID 712196Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 712196
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:8]([O:10][CH2:11][CH3:12])=[O:9].C(=O)([O-])[O-].[K+].[K+].[Br:19][C:20]1[CH:21]=[N:22][C:23](Cl)=[N:24][CH:25]=1.CCCCCC>CN(C=O)C>[Br:19][C:20]1[CH:21]=[N:22][C:23]([N:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]2[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:24][CH:25]=1

Komponenten

6

Edukt 4

HCID 8058HexaneHCID 11430Potassium CarbonateHCID 6066655-Bromo-2-chloropyrimidineHCID 12436225Ethyl piperidine-2-carboxylate--hydrogen chloride (1/1)

Produkt 1

HCID 66977004HCID 66977004, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of ethyl piperidine-2-carboxylate hydrochloride (0.5 g, 2.58 mmol) in DMF (15 mL) was added potassium carbonate (1.77 g, 12.89 mmol) at rt. The mixture was stirred at rt for 10 min followed by addition of 5-bromo-2-chloropyrimidine (0.5 g, 2.58 mmol). The reaction was heated up to 80° C. for 3 h. After reaction completion (by TLC), the mixture was poured onto 100 mL ice-cold water and extracted with EtOAc (3×100 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude residue was purified over 100-200 M silica-gel by using 1.50% EtOAc: hexane to obtain the desired product as an off white solid (0.37 g, 46% yield). MS: 314.08 [M+H]+.

Aufarbeitung

  1. temperatureThe reaction was heated up to 80° C. for 3 h
  2. customAfter reaction completion (by TLC)
  3. extractionextracted with EtOAc (3×100 mL)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated under reduced pressure
  7. customThe crude residue was purified over 100-200 M silica-gel

Quellen und Nachweise

ORD-Eintrag
ord-c89b8155f17d4fe8ba0794a92db4e3d3
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181234B2

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