Ethyl bromopyruvate → HCID 58764108, compound

HRID 2387092Notes

Reaction equation

HRID 2387092 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[N:1]=[C:2]2[N:7]=[CH:6][CH:5]=[N:4][N:3]2[CH:9]=1)=[O:12])[CH3:15]

Participants

4

Reactant 2

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

Product 1

HCID 58764108HCID 58764108, compoundYield 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-91101b95cf394fe491032984f05226f9
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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