Bromine → HCID 178461590, Verbindung

HRID 522810Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 522810
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][C@H:12]2[CH3:17])[N:3]=1.[Br:18]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[Br:18][C:7]1[NH:8][C:9]2[C:5]([N:6]=1)=[C:4]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][C@H:12]1[CH3:17])[N:3]=[C:2]([Cl:1])[N:10]=2

Komponenten

5

Edukt 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 178461592HCID 178461592, Verbindung

Produkt 1

HCID 178461590HCID 178461590, VerbindungAusbeute 39,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-6-((R)-3-methyl-morpholin-4-yl)-9H-purine (950 mg, 3.74 mmol) in CH2Cl2(19 mL) was added bromine (0.23 mL, 4.49 mmol). The mixture was stirred at ambient temperature for 19 hours. Saturated sodium thiosulfate was added. The aqueous layer was extracted with dichloromethane two times. Organic layers were combined and dried over Na2SO4 and solvent was removed under reduced pressure. The crude was purified by flash column chromatography (0-70% EtOAc/cyclohexane gradient) to furnish product as a white solid (495 mg, 39%). LC-MS at 254 nm; [M+H] 334.1; Rt 0.89 min; (LCMS method 1).

Aufarbeitung

  1. extractionThe aqueous layer was extracted with dichloromethane two times
  2. dry with materialdried over Na2SO4 and solvent
  3. customwas removed under reduced pressure
  4. customThe crude was purified by flash column chromatography (0-70% EtOAc/cyclohexane gradient)

Quellen und Nachweise

ORD-Eintrag
ord-9d7b07c8173d4d5faf5ab734bd8057fa
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09334271B2

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