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

HRID 472047Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 472047
[C:1]([O-:4])([O-])=O.[Cs+].[Cs+].Cl[C:8]1[N:13]=[C:12]([N:14]2[C:18]3=[CH:19][N:20]=[C:21]([C:23]4[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:24]=4[CH3:30])[CH:22]=[C:17]3[C:16]([CH:31]([OH:37])[CH:32]([CH2:35][CH3:36])[CH2:33][CH3:34])=[CH:15]2)[CH:11]=[C:10]([CH2:38][CH3:39])[N:9]=1>CO>[CH3:30][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]([CH3:29])[C:23]=1[C:21]1[CH:22]=[C:17]2[C:16]([CH:31]([OH:37])[CH:32]([CH2:33][CH3:34])[CH2:35][CH3:36])=[CH:15][N:14]([C:12]3[CH:11]=[C:10]([CH2:38][CH3:39])[N:9]=[C:8]([O:4][CH3:1])[N:13]=3)[C:18]2=[CH:19][N:20]=1

Komponenten

4

Edukt 2

HCID 10796Cesium carbonateHCID 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

Produkt 1

HCID 582699311-[5-(2,6-dimethyl-phenyl)-1-(6-ethyl-2-methoxy-pyrimidin-4-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-ethyl-butan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Cs2CO3 (85 mg, 0.26 mmol) is added 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-ol (100 mg, 0.22 mmol) in MeOH (4 mL). The mixture is heated at 60° C. for 30 min. The mixture is concentrated under reduced pressure, diluted with water (5 mL), and the product is extracted with DCM. The combined organic extracts are washed with brine, dried (Na2SO4), and concentrated under reduced pressure. Chromatography of the residue silica gel (hexane-EtOAc, 1:1) gives 1-[5-(2,6-dimethyl-phenyl)-1-(6-ethyl-2-methoxy-pyrimidin-4-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-ethyl-butan-1-ol as colorless oil: 1H NMR (CDCl3) 10.18 (s, 1H), 8.39 (s, 1H), 7.54 (s, 1H), 7.27-7.12 (m, 3H), 6.41 (s, 1H), 5.00 (d, J=6 Hz, 1H), 4.12 (s, 3H), 2.78 (dd, J=7, 15 Hz, 2H), 2.075 (s, 6H), 1.39 (t, J=7 Hz), 2.05-1.26 (m, 5H), 0.92 (t, J=7 Hz, 6H); LCMS (1) m/z 459.33 (2.65 min).

Aufarbeitung

  1. concentrationThe mixture is concentrated under reduced pressure
  2. additiondiluted with water (5 mL)
  3. extractionthe product is extracted with DCM
  4. washThe combined organic extracts are washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6a9f7ff1133e41839da6ea84e96d5d04
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633193B2

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