Ethyl bromopyruvate → HCID 57757876, compound

HRID 712194Notes

Reaction equation

HRID 712194 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH2:9])[CH:3]=1.Br[CH2:11][C:12](=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14]>CCO>[NH2:8][C:6]1[N:5]2[CH:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:9]=[C:4]2[CH:3]=[C:2]([Br:1])[CH:7]=1

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 114353934-Bromo-2,6-diaminopyridine

Product 1

HCID 57757876HCID 57757876, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-bromopyridine-2,6-diamine (3 g, 15.96 mmol) was dissolved in EtOH (300 mL). Ethyl bromopyruvate (2.34 mL, 16.8 mmol, 90% tech grade) was added. The mixture was heated at reflux for 5 h. The solvent was evaporated under reduced pressure to give a dark tan foam which was triturated with 200 mL of saturated NaHCO3 overnight. The solids were filtered, washed with 2×10 mL of saturated NaHCO3, then triturated with EtOAc (100 mL) twice, filtered and air dried to give the desired product as a tan powder weighing 3.15 g (70%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 5 h
  3. customThe solvent was evaporated under reduced pressure
  4. customto give a dark tan foam which
  5. customwas triturated with 200 mL of saturated NaHCO3 overnight
  6. filtrationThe solids were filtered
  7. washwashed with 2×10 mL of saturated NaHCO3
  8. customtriturated with EtOAc (100 mL) twice
  9. filtrationfiltered
  10. customair dried

Sources & evidence

ORD record
ord-fecbbb9d758f45e5b1a6ee096673e414
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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