Cesium carbonate → 2-(3-(3-Chloropyrazin-2-yl)azetidin-1-yl)quinazoline

HRID 1850244

Reaktionsgleichung

Reaktionsgleichung von HRID 1850244
Cl.[NH:2]1[CH2:5][CH:4]([C:6]2[C:11]([Cl:12])=[N:10][CH:9]=[CH:8][N:7]=2)[CH2:3]1.Cl[C:14]1[N:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[Cl:12][C:11]1[C:6]([CH:4]2[CH2:5][N:2]([C:14]3[N:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]=3)[CH2:3]2)=[N:7][CH:8]=[CH:9][N:10]=1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 740542-ChloroquinazolineHCID 71743784HCID 71743784, Verbindung

Produkt 1

HCID 585467542-(3-(3-Chloropyrazin-2-yl)azetidin-1-yl)quinazolineAusbeute 47,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

2-(Azetidin-3-yl)-3-chloropyrazine hydrochloride (8) (1.50 g, 7.28 mmol), 2-chloroquinazoline (1.20 g, 7.28 mmol, Parkway Scientific), and cesium carbonate (5.22 g, 16.0 mmol, Fluka) were mixed in DMF (30 mL) in a round bottom flask under a nitrogen atmosphere. The mixture was stirred at 110° C. for 17 h. The reaction mixture was cooled to RT, diluted with water, and extracted with EtOAc (2×). The combined organic extracts were washed with saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude mixture was purified via silica gel flash column chromatography eluting with 0% to 100% EtOAc in hexanes to give 1.02 g (47%) of a yellow amorphous solid.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic extracts were washed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude mixture was purified via silica gel flash column chromatography
  8. washeluting with 0% to 100% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-6fd04f14529d4780856ef1fe8d9ee5a6
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957073B2

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