Water → Methyl 8-chloroimidazo[1,2-A]pyrazine-2-carboxylate

HRID 513212

Reaktionsgleichung

Reaktionsgleichung von HRID 513212
[Cl:1][C:2]1[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][N:7]=1.C(=O)(O)[O-].[Na+].Br[CH2:15][C:16](=O)[C:17]([O:19][CH3:20])=[O:18].O>C(#N)C>[Cl:1][C:2]1[C:3]2[N:4]([CH:15]=[C:16]([C:17]([O:19][CH3:20])=[O:18])[N:8]=2)[CH:5]=[CH:6][N:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 2762242-Amino-3-chloropyrazineHCID 352524Methyl 3-BromopyruvateHCID 516892Sodium Bicarbonate

Produkt 1

HCID 71743177Methyl 8-chloroimidazo[1,2-A]pyrazine-2-carboxylateAusbeute 70,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 3-chloropyrazin-2-amine (52 g, 401 mmol) in acetonitrile (750 mL) under N2 was added sodium bicarbonate (67.4 g, 803 mmol), and then methyl bromopyruvate (97 mL, 803 mmol). The mixture was then heated to 80° C. for 4 hours and then cooled to r.t. The reaction was then diluted water (2200 mL) and stirred for 30 minutes. The resulting solids were filtered, azeotroped with EtOAc (2 L), and dried overnight at 40° C. under vacuum and nitrogen sweep to give the title compound (60 g). LRMS (ESI) calc (M+H)+=212.0. found 212.0

Aufarbeitung

  1. temperaturecooled to r.t
  2. filtrationThe resulting solids were filtered
  3. customazeotroped with EtOAc (2 L)
  4. customdried overnight at 40° C. under vacuum and nitrogen sweep

Quellen und Nachweise

ORD-Eintrag
ord-32b09f46a1bf42d2b54a87d4ee296622
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102673B2

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