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

HRID 513212

Reaction equation

HRID 513212 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 71743177Methyl 8-chloroimidazo[1,2-A]pyrazine-2-carboxylateYield 70.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-32b09f46a1bf42d2b54a87d4ee296622
Source dataset
uspto-grants-2015_08
Patent number
US09102673B2

Linked notes

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