Ethyl bromopyruvate → Imidazo[1,2-b][1,2,4]triazine-carboxylic acid ethyl ester

HRID 859701

Reaction equation

HRID 859701 reaction equation
[NH2:1][C:2]1[N:3]=[N:4][CH:5]=[CH:6][N:7]=1.Br[CH2:9][C:10](=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12]>C(O)C>[CH2:14]([O:13][C:11]([C:10]1[CH:9]=[N:1][C:2]2[N:4]([CH:5]=[CH:6][N:7]=2)[N:3]=1)=[O:12])[CH3:15]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 707153-Amino-1,2,4-triazine

Product 1

HCID 69588513Imidazo[1,2-b][1,2,4]triazine-carboxylic acid ethyl esterYield 1.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-amino-1,2,4-triazine (5.0 g, 52 mmol) and ethyl bromopyruvate (11 mL, 88 mmol) in ethanol (50 mL) was heated to reflux for 20 minutes. The reaction was cooled to room temperature, and then partitioned between 200 mL of EtOAc and 200 mL of water. The layers were separated, and the organic layer was dried over MgSO4. The solids were removed by filtration, and then the solvent was removed by rotary evaporation. The residue was purified by chromatography (90 g SiO2, 50 to 70% EtOAc in hexanes) to give the desired product (181 mg, 1.8%). MS (ESI): 192.4 (M+H)+.

Workup

  1. temperatureto reflux for 20 minutes
  2. custompartitioned between 200 mL of EtOAc and 200 mL of water
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried over MgSO4
  5. customThe solids were removed by filtration
  6. customthe solvent was removed by rotary evaporation
  7. customThe residue was purified by chromatography (90 g SiO2, 50 to 70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b58162468cf648cfb6a71d2c4072f883
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Linked notes

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