m-Chloroperbenzoic acid → HCID 178504621, Verbindung

HRID 1809692Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1809692
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH3:12][S:13][C:14]1[N:19]=[C:18]([C:20]2[C:28]3[C:23](=[N:24][C:25]([NH:29][CH2:30][CH2:31][OH:32])=[N:26][CH:27]=3)[NH:22][N:21]=2)[CH:17]=[CH:16][N:15]=1>ClCCl.CO>[CH3:12][S:13]([C:14]1[N:19]=[C:18]([C:20]2[C:28]3[C:23](=[N:24][C:25]([NH:29][CH2:30][CH2:31][OH:32])=[N:26][CH:27]=3)[NH:22][N:21]=2)[CH:17]=[CH:16][N:15]=1)=[O:9]

Komponenten

5

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 1785034392-[3-(2-methylsulfanyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-ethanol

Produkt 1

HCID 178504621HCID 178504621, VerbindungAusbeute 257,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

m-CPBA (797 mg, 4.62 mmol) was added slowly to a solution of 2-[3-(2-Methylsulfanyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-ethanol (from Example 20 supra) (0.7 g, crude) in a mixture of dichloromethane and methanol (40 mL, 1:1). The reaction mixture was stirred at room temperature for 30 minutes. The solvent was then removed under reduced pressure and the solid was purified by column chromatography (silica gel, 10 g, 200-300 mesh, eluting with dichloromethane:methanol, 5:1) to afford 2-[3-(2-methanesulfinyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-ethanol (Yield 1.9 g, crude). LC-MS: [M+H]+ 320.

Aufarbeitung

  1. customThe solvent was then removed under reduced pressure
  2. customthe solid was purified by column chromatography (silica gel, 10 g, 200-300 mesh, eluting with dichloromethane:methanol, 5:1)

Quellen und Nachweise

ORD-Eintrag
ord-4ba1e2abe3164c5ba8a3bfb6202489e6
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362023B2

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