Cesium carbonate → (RS)-N-(Ethoxycarbonyl)-S-[3-({[4-(isopropylamino)-6-methoxyquinazolin-7-yl]oxy}-methyl)phenyl]-S-methylsulphoximide

HRID 249973Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 249973
[CH:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([OH:17])=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[CH:7][N:6]=1)([CH3:3])[CH3:2].Br[CH2:19][C:20]1[CH:21]=[C:22]([S:26]([CH3:34])(=[N:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:27])[CH:23]=[CH:24][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH2:32]([O:31][C:29]([N:28]=[S:26]([C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([CH2:19][O:17][C:11]2[CH:10]=[C:9]3[C:14]([C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[N:6][CH:7]=[N:8]3)=[CH:13][C:12]=2[O:15][CH3:16])[CH:21]=1)([CH3:34])=[O:27])=[O:30])[CH3:33]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 57788029(RS)-S-[3-(bromomethyl)phenyl]-N-(ethoxycarbonyl)-S-methylsulphoximideHCID 1358608004-(Isopropylamino)-6-methoxyquinazolin-7-ol

Produkt 1

HCID 57787986(RS)-N-(Ethoxycarbonyl)-S-[3-({[4-(isopropylamino)-6-methoxyquinazolin-7-yl]oxy}-methyl)phenyl]-S-methylsulphoximide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

4-(Isopropylamino)-6-methoxyquinazolin-7-ol (65 mg, 0.21 mmol) and (RS)-S-[3-(bromomethyl)phenyl]-N-(ethoxycarbonyl)-S-methylsulphoximide (102 mg, 0.27 mmol) are suspended in 14 ml of acetone. After addition of caesium carbonate (2427 mg, 0.74 mmol), the reaction mixture is stirred at reflux for 3 hours. After cooling, the batch is concentrated, the residue is taken up in ethyl acetate, and the organic phase is washed with water and dried over sodium sulphate. After removal of the solvent, the residue (144 mg, 97% of theory) is employed in the next reaction without further purification.

Aufarbeitung

  1. temperatureat reflux for 3 hours
  2. temperatureAfter cooling
  3. concentrationthe batch is concentrated
  4. washthe organic phase is washed with water
  5. dry with materialdried over sodium sulphate
  6. customAfter removal of the solvent
  7. customthe residue (144 mg, 97% of theory) is employed in the next reaction without further purification

Quellen und Nachweise

ORD-Eintrag
ord-45546735ad3c4b4490aea5f859f67e4b
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863283B2

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