Triethylamine → HCID 22672632, compound

HRID 1006687Notes

Reaction equation

HRID 1006687 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([CH3:9])=[CH:4][N:3]=1.Br[CH:11]([CH3:15])[C:12](=O)[CH3:13].C(N(CC)CC)C>C(O)C>[NH2:8][C:7]1[C:2]2[N:3]([C:11]([CH3:15])=[C:12]([CH3:13])[N:1]=2)[CH:4]=[C:5]([CH3:9])[CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 131422-Butanone, 3-bromo-2×HCID 107018255-Methylpyridine-2,3-diamine

Product 1

HCID 22672632HCID 22672632, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,3-diamino-5-methylpyridine (2.0 g, 16 mmol) in ethanol (100 ml) was added 3-bromo-2-butanon (2.4 g, 16 mmol). The reaction mixture was refluxed for 16 h. An additional amount of 3-bromo-2-butanon (1.0 g 6.7 mmol) and triethylamine (1.0 g, 9.9 mmol) were added and the mixture was refluxed for 2 h. The ethanol was evaporated under reduced pressure and the residue was treated with methylene chloride and a solution of bicarbonate. The organic layer was separated, dried over sodium sulfate and evaporated under reduced pressure. The oily residue was purified by column chromatography on silica gel, using methanol:methylene chloride (1:20) as eluent to give the desired product (1.05 g, 37%).

Workup

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. temperaturethe mixture was refluxed for 2 h
  3. customThe ethanol was evaporated under reduced pressure
  4. additionthe residue was treated with methylene chloride
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe oily residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-442f8ac8fc574ddea2a5d56f1b350dfb
Source dataset
uspto-grants-2004_09
Patent number
US06790960B2

Reaction notes

Loading…