Sodium borohydride → 1-[1-(2-chloro-6-ethyl-pyrimidin-4-yl)-5-(2,6-dimethyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-ethyl-butan-1-ol

HRID 602549Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 602549
[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[C:12]3=[CH:13][N:14]=[C:15]([C:17]4[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=4[CH3:24])[CH:16]=[C:11]3[C:10]([C:25](=[O:31])[CH:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[CH:9]2)[CH:5]=[C:4]([CH2:32][CH3:33])[N:3]=1.[BH4-].[Na+]>C(O)C.O>[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[C:12]3=[CH:13][N:14]=[C:15]([C:17]4[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=4[CH3:24])[CH:16]=[C:11]3[C:10]([CH:25]([OH:31])[CH:26]([CH2:27][CH3:28])[CH2:29][CH3:30])=[CH:9]2)[CH:5]=[C:4]([CH2:32][CH3:33])[N:3]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 866240811-[1-(2-chloro-6-ethyl-pyrimidin-4-yl)-5-(2,6-dimethyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-ethyl-butan-1-one

Produkt 1

HCID 866240821-[1-(2-chloro-6-ethyl-pyrimidin-4-yl)-5-(2,6-dimethyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-ethyl-butan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 19096565Water ethanolLösungsmittel

Versuchsvorschrift

To a solution of 1-[1-(2-chloro-6-ethyl-pyrimidin-4-yl)-5-(2,6-dimethyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-ethyl-butan-1-one (150 mg, 0.32 mmol) in a (4:1) mixture EtOH—H2O (4 mL) at −30° C., NaBH4 (70 mg, 1.8 mmol) is added, and the mixture is allowed gradually warm up to room temperature at which the reaction is maintained for 2 h. The mixture is concentrated under reduced pressure, and an aqueous saturated Rochelle's salt solution (10 mL) is added. The resulting suspension is stirred at room temperature for 1 h, and the product is extracted with DCM. The obtained solution is washed with brine, dried (Na2SO4), and concentrated under reduced pressure. Chromatography of the residue on silica gel (hexane-EtOAc, 1:1) gives 1-[1-(2-chloro-6-ethyl-pyrimidin-4-yl)-5-(2,6-dimethyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-ethyl-butan-1-ol as colorless oil.

Aufarbeitung

  1. temperatureis maintained for 2 h
  2. concentrationThe mixture is concentrated under reduced pressure
  3. additionan aqueous saturated Rochelle's salt solution (10 mL) is added
  4. extractionthe product is extracted with DCM
  5. washThe obtained solution is washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-90008864445f496aa8d8ada530e43d57
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906528B2

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