Cesium carbonate → 3-[(6-[3-(1-Methylimidazolin-2-yl)phenoxy]-2-phenylpyrimidin-4-yl)oxy]-4-(benzyloxy)benzonitrile

HRID 841982

Reaktionsgleichung

Reaktionsgleichung von HRID 841982
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([O:14][C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=2[O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:18]#[N:19])[CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[OH:37][C:38]1[CH:39]=[C:40]([C:44]2[N:45]([CH3:49])[CH2:46][CH2:47][N:48]=2)[CH:41]=[CH:42][CH:43]=1>CS(C)=O>[CH3:49][N:45]1[CH2:46][CH2:47][N:48]=[C:44]1[C:40]1[CH:39]=[C:38]([CH:43]=[CH:42][CH:41]=1)[O:37][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([O:14][C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=2[O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:18]#[N:19])[CH:3]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 114238803-(1-Methylimidazolin-2-yl)phenolHCID 154807033-[(6-Chloro-2-phenylpyrimidin-4-yl)oxy]-4-(benzyloxy)benzonitrile

Produkt 1

HCID 154807043-[(6-[3-(1-Methylimidazolin-2-yl)phenoxy]-2-phenylpyrimidin-4-yl)oxy]-4-(benzyloxy)benzonitrileAusbeute 37,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To 3-[(6-chloro-2-phenylpyrimidin-4-yl)oxy]-4-(benzyloxy)benzonitrile (1.0 g, 2.4 mmol) in DMSO (12 mL) was added Cs2CO3 (0.8 g, 2.5 mmol) and 2-(3-hydroxyphenyl)-1-methylimidazoline (0.44 g, 2.5 mmol). After stirring in an oil bath at 50° C. for 24 hours, the reaction was partitioned with water and ethyl acetate. The layers were separated, washed with water and brine, dried (Na2SO4), and the solvent was removed in vacuo. The residue was chromatographed on silica gel with CH2CL2/MeOH/NH4OH (120/5/1) to give 0.5 g of 3-[(6-[3-(1-methylimidazolin-2-yl)phenoxy]-2-phenylpyrimidin-4-yl)oxy]-4-(benzyloxy)benzonitrile.

Aufarbeitung

  1. customthe reaction was partitioned with water and ethyl acetate
  2. customThe layers were separated
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. customthe solvent was removed in vacuo
  6. customThe residue was chromatographed on silica gel with CH2CL2/MeOH/NH4OH (120/5/1)

Quellen und Nachweise

ORD-Eintrag
ord-84f7323fa3c74497ac86cfde93961eea
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06372751B1

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