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Cesium carbonate → 2-(4-Fluorophenyl)-8-methyl-3-(2-methylsulfanylpyrimidin-4-yl)-imidazo[1,2-a]pyrazine

HRID 2233098
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2233098
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[C:15]([CH3:16])=[N:14][CH:13]=[CH:12][N:11]3[CH:17]=2)=[CH:4][CH:3]=1.I[C:19]1[CH:24]=[CH:23][N:22]=[C:21]([S:25][CH3:26])[N:20]=1.C([O-])([O-])=O.[Cs+].[Cs+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>O.CC([O-])=O.CC([O-])=O.[Pd+2].CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[C:15]([CH3:16])=[N:14][CH:13]=[CH:12][N:11]3[C:17]=2[C:19]2[CH:24]=[CH:23][N:22]=[C:21]([S:25][CH3:26])[N:20]=2)=[CH:6][CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 38589014-Iodo-2-(methylthio)pyrimidineHCID 574387492-(4-Fluorophenyl)-8-methylimidazo[1,2-a]pyrazine

Produkt 1

HCID 574387482-(4-Fluorophenyl)-8-methyl-3-(2-methylsulfanylpyrimidin-4-yl)-imidazo[1,2-a]pyrazineAusbeute 58,3 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Into a flask was added 2-(4-fluorophenyl)-8-methylimidazo[1,2-a]pyrazine (4.8 g, 21.0 mmol), 4-iodo-2-(methylthio)pyrimidine (Frontier, 9.4 g, 31.7 mmol), Cs2CO3 (10.3 g, 31.7 mmol), PPh3 (2.2 g, 8.4 mmol), and DMF (50 mL). The mixture was degassed under vacuum and back-filled with N2. The mixture was charged with Pd(OAc)2 (0.95 g, 4.2 mmol) and heated at about 100° C. for about 16 h. The mixture was cooled to ambient temperature, diluted with water (200 mL), and extracted with DCM (3×200 mL). The combined organic layers were washed with brine (200 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification by flash column chromatography (0-5% MeOH:DCM) followed by trituration in EtOAc yielded the title compound (4.30 g, 58% yield): LC/MS (Table 1, Method b) Rt=2.2 min; MS m/z: 352.3 (M+H)+.

Aufarbeitung

  1. customThe mixture was degassed under vacuum
  2. additionback-filled with N2
  3. temperatureThe mixture was cooled to ambient temperature
  4. extractionextracted with DCM (3×200 mL)
  5. washThe combined organic layers were washed with brine (200 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customPurification by flash column chromatography (0-5% MeOH:DCM)

Quellen und Nachweise

ORD-Eintrag
ord-80810ade611f43f5a5d88eda1a707725
Quelldatensatz
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07709468B2

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