StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Bromide ion → 2-Butoxy-9-(1-tert-butoxycarbonylpiperidin-4-ylmethyl)-8-methoxyadenine

HRID 2403788
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2403788
C(=O)([O-])[O-].[K+].[K+].FC(F)(F)C(O)=O.[CH2:14]([O:18][C:19]1[N:27]=[C:26]2[C:22]([N:23]=[C:24]([O:28][CH3:29])[NH:25]2)=[C:21]([NH2:30])[N:20]=1)[CH2:15][CH2:16][CH3:17].Br[CH2:32][CH:33]1[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:35][CH2:34]1.[Br-]>CN(C)C=O.O>[NH2:30][C:21]1[N:20]=[C:19]([O:18][CH2:14][CH2:15][CH2:16][CH3:17])[N:27]=[C:26]2[C:22]=1[N:23]=[C:24]([O:28][CH3:29])[N:25]2[CH2:32][CH:33]1[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:43])([CH3:45])[CH3:44])=[O:40])[CH2:35][CH2:34]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 259Bromide ionHCID 11430Potassium CarbonateHCID 15512811tert-Butyl 4-(bromomethyl)piperidine-1-carboxylateHCID 178450370HCID 178450370, Verbindung

Produkt 1

HCID 583060912-Butoxy-9-(1-tert-butoxycarbonylpiperidin-4-ylmethyl)-8-methoxyadenineAusbeute 94,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Potassium carbonate (650 mg) was added to a solution of 2-butoxy-8-methoxy-9H-purin-6-amine trifluoroacetate salt (550 mg) in dry N,N-dimethylformamide (5.5 ml) and the reaction mixture heated at 60° C. for 1 hour. 1,1-Dimethylethyl 4-(bromomethyl)-1-piperidinecarboxylate (500 mg) was added using additional DMF (1.5 ml) to transfer the residual bromide and the reaction mixture stirred at 50° C. for 3 hours. After 16 hours at room temperature, heating at 50° C. was continued for another 5 hours to complete the reaction. Water was added and the reaction mixture extracted three times with ethyl acetate. The combined organic extracts were washed with water, dried over anhydrous sodium sulfate, filtered, concentrated and dried under high vacuum. Purification by chromatography on silica gel eluting with a gradient of 1-2.5% methanol in chloroform afforded the title compound as yellow solid (640 mg).

Aufarbeitung

  1. waitAfter 16 hours at room temperature
  2. temperatureheating at 50° C.
  3. waitwas continued for another 5 hours
  4. customthe reaction
  5. extractionthe reaction mixture extracted three times with ethyl acetate
  6. washThe combined organic extracts were washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customdried under high vacuum
  11. customPurification by chromatography on silica gel eluting with a gradient of 1-2.5% methanol in chloroform

Quellen und Nachweise

ORD-Eintrag
ord-e6f4612d8b29448b9741823eb32b5dce
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08802684B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion