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Dimethylformamide → 2-Chloro-6-[(3S)-3-methylmorpholin-4-yl]-9-(2,2,2-trifluoroethyl)-9H-purine

HRID 421434
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 421434
[F:1][C:2]([F:13])([F:12])[CH2:3]OS(C(F)(F)F)(=O)=O.CN(C)C=O.[Cl:19][C:20]1[N:28]=[C:27]2[C:23]([N:24]=[CH:25][NH:26]2)=[C:22]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][C@@H:30]2[CH3:35])[N:21]=1.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:19][C:20]1[N:28]=[C:27]2[C:23]([N:24]=[CH:25][N:26]2[CH2:3][C:2]([F:13])([F:12])[F:1])=[C:22]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][C@@H:30]2[CH3:35])[N:21]=1
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Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 178461593HCID 178461593, Verbindung

Produkt 1

HCID 593335792-Chloro-6-[(3S)-3-methylmorpholin-4-yl]-9-(2,2,2-trifluoroethyl)-9H-purineAusbeute 76,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

2,2,2-Trifluoroethyltrifluoromethyl sulfonate (83 μl, 0.57 mmol) was added to an N,N-dimethylformamide (5 ml) suspension of 2-chloro-6-[(3S)-3-methylmorpholin-4-yl]-9H-purine (132 mg, 0.52 mmol) and potassium carbonate (86 mg, 0.62 mmol) with ice cooling. The reaction mixture was stirred at 50° C. for 2 hours and returned to room temperature. Water was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate and, after filtration, the filtrate was concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography (30% ethyl acetate:hexane) to give the title compound (133 mg, 76%) as a solid.

Aufarbeitung

  1. customreturned to room temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationafter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by flash silica gel column chromatography (30% ethyl acetate:hexane)

Quellen und Nachweise

ORD-Eintrag
ord-1902e49eae69493d8a55f4100beae7d2
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08097622B2

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