N-bromobutanimide → 8-Bromo-2-{[2-(methoxy)ethyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

HRID 1011024Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1011024
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[CH:11][N:12]2[CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)=[C:8]([NH2:21])[N:7]=1.[Br:22]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:22][C:11]1[N:12]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[C:13]2[C:9]([N:10]=1)=[C:8]([NH2:21])[N:7]=[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[N:14]=2

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 57699621[2-(Methoxy)ethyl]oxy-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Produkt 1

HCID 576997398-Bromo-2-{[2-(methoxy)ethyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amineAusbeute 70,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-{[2-(Methoxy)ethyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (1.61 g) was dissolved in chloroform (20 mL) and cooled to 0° C. To this solution was then added N-bromosuccinimide (1.02 g) gradually, keeping the temperature at ˜2° C. The reaction was stirred at 2° C. for around 15 minutes before being allowed to warm to room temperature. The reaction mixture was then stirred under nitrogen for 5 hours. The reaction mixture was quenched with water (100 mL) and stirred rapidly before the organic layer was separated using a hydrophobic frit. The organic was evaporated under reduced pressure to give a dark brown gum. This material was purified by silica chromatography (ISCO) eluting initially with 0-70% ethyl acetate: cyclohexane holding isocratic at 70% ethyl acetate; cyclohexane until a minor impurity was eluted. The gradient was then resumed from 70%-95% ethyl acetate: cyclohexane. This gave the title compound as a white solid (1.4489 g)

Aufarbeitung

  1. customat ˜2° C
  2. temperatureto warm to room temperature
  3. stirringThe reaction mixture was then stirred under nitrogen for 5 hours
  4. customThe reaction mixture was quenched with water (100 mL)
  5. stirringstirred rapidly before the organic layer
  6. customwas separated
  7. customThe organic was evaporated under reduced pressure
  8. customto give a dark brown gum
  9. customThis material was purified by silica chromatography (ISCO)
  10. washeluting initially with 0-70% ethyl acetate
  11. washcyclohexane until a minor impurity was eluted

Quellen und Nachweise

ORD-Eintrag
ord-8614b8e95dbb4d0894a89e294f1ca779
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977344B2

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