Ethyl bromopyruvate → HCID 19701264, compound

HRID 861981Notes

Reaction equation

HRID 861981 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][CH:3]=1.Br[CH2:11][C:12](=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14]>COCCOC>[OH:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]2[N:7]([CH:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:1]=2)[CH:6]=1

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 2794829(6-Aminopyridin-3-yl)methanol

Product 1

HCID 19701264HCID 19701264, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a 100 mL flask under a N2 atmosphere were added DME (35 mL) and the product from Example 9 (0.60 g, 4.8 mmol). After stirring for 20 min, ethyl bromopyruvate (1.03 g, 5.3 mmol) was added and the reaction was allowed to stir at room temperature for 16 h. The resulting precipitate was filtered and washed once with Et2O. The solid was suspended in abs EtOH (35 mL) and heated to reflux for 2 h. The resulting solution was cooled to room temperature and all solvent removed in vacuo. Aqueous K2CO3 was added to the residue, and the product was extracted with CH2Cl2. The extracts were dried (MgSO4) and stripped to leave 0.793 g (75%) of title product.

Workup

  1. stirringto stir at room temperature for 16 h
  2. filtrationThe resulting precipitate was filtered
  3. washwashed once with Et2O
  4. temperatureheated
  5. temperatureto reflux for 2 h
  6. customall solvent removed in vacuo
  7. additionAqueous K2CO3 was added to the residue
  8. extractionthe product was extracted with CH2Cl2
  9. dry with materialThe extracts were dried (MgSO4)

Sources & evidence

ORD record
ord-d75fc3b9a40543a0b64a75cb4aee1699
Source dataset
uspto-grants-1998_02
Patent number
US05716964

Reaction notes

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