Trifluoroacetic acid → HCID 66597624, Verbindung

HRID 2276292Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2276292
FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1.[CH2:16]([C:18]1[N:19]([CH3:43])[C:20]2[C:25]([N:26]=1)=[C:24]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)[N:23]=[C:22]([S:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1)[N:21]=2)[CH3:17].[N+:44](C1C=C(C=CC=1OC)CBr)([O-:46])=[O:45]>CC(C)=O>[CH2:16]([C:18]1[N:19]([CH3:43])[C:20]2[C:25]([N:26]=1)=[C:24]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)[N:23]=[C:22]([S:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[C:37]([N+:44]([O-:46])=[O:45])[CH:36]=1)[N:21]=2)[CH3:17]

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 115796484-(Bromomethyl)-1-methoxy-2-nitrobenzeneHCID 49819035HCID 49819035, Verbindung

Produkt 1

HCID 66597624HCID 66597624, VerbindungAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Trifluoroacetic acid (40 ml) and anisole (2.7 ml, 15 mmol) were added to 8-ethyl-2-(4-methoxybenzylsulfanyl)-9-methyl-6-morpholino-9H-purine (5.0 g, 12.5 mmol), and heated and stirred at 80° C. overnight. After distilling away trifluoroacetic acid under reduced pressure, neutralization was performed by adding excess triethylamine under ice cooling. After distilling away triethylamine under reduced pressure, the residue was dissolved in acetone (50 ml) and 3-nitro-4-methoxybenzyl bromide (3.69 g, 15 mmol) dissolved in acetone (10 ml) was added. After stirring at room temperature for 2.5 hours, the reaction solution was concentrated under reduced pressure, the residue was made to have a pH of approximately 7.0 by 2N—NaOH solution, and the precipitated crystals were collected by filtration. The obtained crystals were washed sequentially with hexane and ether to obtain 3.93 g (71% yield) of 8-ethyl-9-methyl-6-morpholino-2-(3-nitro-4-methoxybenzylsulfanyl)-9H-purine.

Aufarbeitung

  1. temperatureheated
  2. distillationAfter distilling away trifluoroacetic acid under reduced pressure, neutralization
  3. additionby adding excess triethylamine under ice cooling
  4. distillationAfter distilling away triethylamine under reduced pressure
  5. dissolutionthe residue was dissolved in acetone (50 ml)
  6. additionwas added
  7. stirringAfter stirring at room temperature for 2.5 hours
  8. concentrationthe reaction solution was concentrated under reduced pressure
  9. filtrationthe precipitated crystals were collected by filtration
  10. washThe obtained crystals were washed sequentially with hexane and ether

Quellen und Nachweise

ORD-Eintrag
ord-cdceeb49d898453a8e2c82956757952a
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09132130B2

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