Hydrochloric Acid → (RS)-S-[4-({5-bromo-4-[(1R,2R)-2-hydroxy-1-methylpropoxy]pyrimidin-2-yl}amino)-2-methoxyphenyl]-S-methyl Sulfoximide

HRID 1391443Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1391443
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[NH:10])=[O:9])=[C:4]([O:12][CH3:13])[CH:3]=1.[Br:14][C:15]1[C:16]([O:22][C@H:23]([CH3:27])[C@H:24]([OH:26])[CH3:25])=[N:17][C:18](Cl)=[N:19][CH:20]=1.Cl.C(O)CCC.CO>C(#N)C.O1CCOCC1>[Br:14][C:15]1[C:16]([O:22][C@H:23]([CH3:27])[C@H:24]([OH:26])[CH3:25])=[N:17][C:18]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[NH:10])=[O:9])=[C:4]([O:12][CH3:13])[CH:3]=2)=[N:19][CH:20]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 22439470n-Butanol methanolHCID 59673984(4-Amino-2-methoxyphenyl)(imino)methyl-lambda6-sulfanoneHCID 59674033(2R,3R)-3-(5-bromo-2-chloropyrimidin-4-yloxy)butan-2-ol

Produkt 1

HCID 59674010(RS)-S-[4-({5-bromo-4-[(1R,2R)-2-hydroxy-1-methylpropoxy]pyrimidin-2-yl}amino)-2-methoxyphenyl]-S-methyl Sulfoximide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

220 mg (1.1 mmol) of (RS)-S-(4-amino-2-methoxyphenyl)-S-methyl sulfoximide and 280 mg (1.0 mmol) of (2R,3R)-3-[(5-bromo-2-chloropyrimidin-4-yl)oxy]-butan-2-ol in 10 ml of acetonitrile are mixed with 0.28 ml of a 4N solution of HCl in dioxane and stirred under reflux overnight. It is mixed with 1 ml of a solution of n-butanol/methanol (9:1) and stirred under reflux for another 5 days. The batch is concentrated by evaporation, and the residue is purified by chromatography (DCM/ethanol 8:2). 36 mg (0.1 mmol, corresponding to 8% of theory) of the product is obtained.

Aufarbeitung

  1. temperatureunder reflux overnight
  2. stirringstirred
  3. temperatureunder reflux for another 5 days
  4. concentrationThe batch is concentrated by evaporation
  5. customthe residue is purified by chromatography (DCM/ethanol 8:2)
  6. custom36 mg (0.1 mmol, corresponding to 8% of theory) of the product is obtained

Quellen und Nachweise

ORD-Eintrag
ord-9c56a6a5bb254ee9937e8248fa5c9fdc
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07338958B2

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