N-bromobutanimide → 7-Bromo-2,4-bis(methylthio)imidazo[2,1-f][1,2,4]triazine

HRID 1430803Notes

Reaction equation

HRID 1430803 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([S:9][CH3:10])[C:6]2=[N:11][CH:12]=[CH:13][N:5]2[N:4]=1.[Br:14]N1C(=O)CCC1=O>CN(C=O)C.O>[Br:14][C:13]1[N:5]2[C:6]([C:7]([S:9][CH3:10])=[N:8][C:3]([S:2][CH3:1])=[N:4]2)=[N:11][CH:12]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 106800572,4-Bis(methylthio)imidazo[2,1-f][1,2,4]triazine

Product 1

HCID 574576447-Bromo-2,4-bis(methylthio)imidazo[2,1-f][1,2,4]triazineYield 63.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,4-bis(methylthio)imidazo[2,1-f][1,2,4]triazine (5.27 g, 24.82 mmol) and 1-bromopyrrolidine-2,5-dione (6.19 g, 34.8 mmol) in DMF (15 mL) was stirred at RT for 2 hours. The reaction was diluted with water, and the product extracted with dichloromethane (3×50 mL). The organic layer was washed with brine, dried and concentrated. The crude product mixture was purified via ISCO (0-50% of ethyl acetate/dichloromethane in 10 minutes, 80 g silica column) to give the pure product 7-bromo-2,4-bis(methylthio)imidazo[2,1-f][1,2,4]triazine (4.61 g, 15.83 mmol, 63.8% yield).

Workup

  1. extractionthe product extracted with dichloromethane (3×50 mL)
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe crude product mixture was purified via ISCO (0-50% of ethyl acetate/dichloromethane in 10 minutes, 80 g silica column)

Sources & evidence

ORD record
ord-11ff541745b745fd8b39c81ddc7ab179
Source dataset
uspto-grants-2015_01
Patent number
US08940736B2

Reaction notes

Loading…