N-bromobutanimide → 8-bromo-2-(((S)-pentan-2-yl)oxy)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

HRID 562707Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 562707
[Br:1]N1C(=O)CCC1=O.[CH3:9][C@H:10]([O:14][C:15]1[N:23]=[C:22]2[C:18]([N:19]=[CH:20][N:21]2[CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)=[C:17]([NH2:30])[N:16]=1)[CH2:11][CH2:12][CH3:13]>C(Cl)(Cl)Cl>[Br:1][C:20]1[N:21]([CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[C:22]2[C:18]([N:19]=1)=[C:17]([NH2:30])[N:16]=[C:15]([O:14][C@@H:10]([CH3:9])[CH2:11][CH2:12][CH3:13])[N:23]=2

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 576998322-(((S)-pentan-2-yl)oxy)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Produkt 1

HCID 576998418-bromo-2-(((S)-pentan-2-yl)oxy)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amineAusbeute 98,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

N-Bromosuccinimide (12.16 g, 68.3 mmol) was added portionwise over 5 mins. to a stirred solution of 2-{[(1S)-1-methylbutyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (14.9 g, 48.8 mmol) in chloroform (80 ml) at <5° C. under an atmosphere of nitrogen. The reaction mixture was stirred at <5° C. for 5 hours then washed with saturated sodium hydrogen carbonate solution (80 ml) then water (80 ml). The foam was dissolved in DCM (50 ml) and washed with water (50 ml) then brine (50 ml). The combined aqueous phases were washed with DCM (50 ml). The combined organic layers were dried through a hydrophobic frit, and the solvent removed in vacuo to yield the title compound as an orange foam (18.5 g).

Aufarbeitung

  1. customat <5° C.
  2. washthen washed with saturated sodium hydrogen carbonate solution (80 ml)
  3. dissolutionThe foam was dissolved in DCM (50 ml)
  4. washwashed with water (50 ml)
  5. washThe combined aqueous phases were washed with DCM (50 ml)
  6. customThe combined organic layers were dried through a hydrophobic frit
  7. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-29e41cc9169d456e999bc7d05582e37f
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067426B2

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