2,3-Diaminopyridine → HCID 22997465, compound

HRID 1166172Notes

Reaction equation

HRID 1166172 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:9]([O:11][C:12](=[O:22])[CH:13](Br)[C:14](=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:10].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC>[NH2:8][C:7]1[C:2]2[N:3]([C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([C:12]([O:11][CH2:9][CH3:10])=[O:22])[N:1]=2)[CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 99562,3-DiaminopyridineHCID 10340Sodium CarbonateHCID 11817994HCID 11817994, compound

Product 1

HCID 22997465HCID 22997465, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 2,3-diaminopyridine (13.1 g, 0.12 mol) , 2-bromo-3-oxo-succinic acid diethyl ester (31 g, 0.12 mol) and sodium carbonate (13.2 g, 0.12 mol) in 1,2-dimethoxyethane (200 ml) was refluxed for 20 h. The solvent was evaporated under reduced pressure and the residue was suspended in methylene chloride and filtrated through silica gel. The filtrate was evaporated under reduced pressure to give 10.9 g (33%) of the title compound as an oil.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. filtrationfiltrated through silica gel
  3. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5199ad6fb6e44ecf92a5ac7cdd3d4453
Source dataset
uspto-grants-2003_09
Patent number
US06613775B1

Reaction notes

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