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Sodium Chloride → (RS)-S-[4-({5-bromo-4-[(R)-(2-hydroxy-1,2-dimethylpropyl)amino]pyrimidin-2-yl}amino)phenyl]-S-methyl Sulfoximide

HRID 1391446
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1391446
[Br:1][C:2]1[C:3]([NH:24][C@H:25]([CH3:30])[C:26]([OH:29])([CH3:28])[CH3:27])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:23])(=[N:17]C(OCC)=O)=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.CC[O-].[Na+].[Na+].[Cl-]>C(O)C>[Br:1][C:2]1[C:3]([NH:24][C@H:25]([CH3:30])[C:26]([OH:29])([CH3:27])[CH3:28])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:23])(=[NH:17])=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1
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Komponenten

5

Edukt 3

HCID 5234Sodium ChlorideHCID 2723922Sodium ethoxideHCID 59674007(RS)-S-[4-({5-bromo-4-[(R)-(2-hydroxy-1,2-dimethylpropyl)amino]pyrimidin-2-yl}amino)phenyl]-N-(ethoxycarbonyl)-S-methyl Sulfoximide

Produkt 1

HCID 59674034(RS)-S-[4-({5-bromo-4-[(R)-(2-hydroxy-1,2-dimethylpropyl)amino]pyrimidin-2-yl}amino)phenyl]-S-methyl Sulfoximide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702
Ethanol
Lösungsmittel
2×

Versuchsvorschrift

1.65 g (3.30 mmol) of (RS)-S-[4-({5-bromo-4-[(R)-(2-hydroxy-1,2-dimethylpropyl)amino]pyrimidin-2-yl}amino)phenyl]-N-(ethoxycarbonyl)-S-methyl sulfoximide in 6.5 ml of ethanol is mixed with 19.1 ml (6.69 mmol) of a 0.35 molar solution of NaOEt in ethanol and stirred under reflux for 5 hours. The batch is stirred overnight at room temperature and then added to a saturated NaCl solution. It is extracted with ethyl acetate, and the combined organic phases are dried (Na2SO4), filtered and concentrated by evaporation. The remaining residue is purified by chromatography (DCM/EtOH 9:1). 0.95 g (2.22 mmol, corresponding to 67% of theory) of the product is obtained.

Aufarbeitung

  1. temperatureunder reflux for 5 hours
  2. stirringThe batch is stirred overnight at room temperature
  3. extractionIt is extracted with ethyl acetate
  4. dry with materialthe combined organic phases are dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. customThe remaining residue is purified by chromatography (DCM/EtOH 9:1)
  8. custom0.95 g (2.22 mmol, corresponding to 67% of theory) of the product is obtained

Quellen und Nachweise

ORD-Eintrag
ord-3e54e0cb08064fdf98ba8b331f2d130b
Quelldatensatz
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07338958B2

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