Sodium hydride → HCID 10452270, Verbindung

HRID 222697Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 222697
[H-].[Na+].[CH:3]1([N:7]2[CH2:13][CH2:12][C:11]3[CH:14]=[C:15]([OH:18])[CH:16]=[CH:17][C:10]=3[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4]1.Br[C:20]1[CH:21]=[N:22][C:23]([N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[N:24][CH:25]=1>N1C=CC=CC=1.[Cu]Br>[CH:3]1([N:7]2[CH2:8][CH2:9][C:10]3[CH:17]=[CH:16][C:15]([O:18][C:20]4[CH:25]=[N:24][C:23]([N:26]5[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]5)=[N:22][CH:21]=4)=[CH:14][C:11]=3[CH2:12][CH2:13]2)[CH2:6][CH2:5][CH2:4]1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 36146825-Bromo-2-(piperidin-1-yl)pyrimidineHCID 100820813-Cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[D]azepin-7-OL

Produkt 1

HCID 10452270HCID 10452270, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24593copper(I) bromideKatalysatorHCID 1049PyridineLösungsmittel

Versuchsvorschrift

Sodium hydride (60% disp. in mineral oil, 44 mg, 1.1 mmol) was added to a stirred solution of 3-cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol (E3) (200 mg, 0.92 mmol) and copper (I) bromide (184 mg, 1.3 mmol) in pyridine (10 ml) at 0° C. After stirring for 0.5 hour at room temperature, 5-bromo-2-(1-piperidinyl)pyrimidine (D32) (0.669 g, 2.8 mmol) was added and the reaction mixture heated at reflux for 2 hours. The reaction was allowed to cool, filtered and the filtrate was concentrated in vacuo. The crude residue was dissolved with ethyl acetate and washed with water and brine. The organic layer was dried (magnesium sulfate), filtered and concentrated in vacuo. Purification of the resulting residue by column chromatography eluting with a mixture of 0.880 ammonia:ethanol:dichloromethane (0.25:2.25:97.5 to 1:9:90) afforded the title compound (E140). MS (ES+) m/e 379 [M+H]+.

Aufarbeitung

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 2 hours
  3. temperatureto cool
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo
  6. dissolutionThe crude residue was dissolved with ethyl acetate
  7. washwashed with water and brine
  8. dry with materialThe organic layer was dried (magnesium sulfate)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customPurification of the resulting residue by column chromatography
  12. washeluting with a mixture of 0.880 ammonia:ethanol:dichloromethane (0.25:2.25:97.5 to 1:9:90)

Quellen und Nachweise

ORD-Eintrag
ord-1adc21d44bd24306a958c5fcc511e3f6
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207331B2

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