1,2,4,5-Tetrazine → 4-(2-Fluoro-5-nitrophenyl)-5-trimethylsilanylpyridazine

HRID 2184056Notes

Reaction equation

HRID 2184056 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]#[C:12][Si:13]([CH3:16])([CH3:15])[CH3:14].[N:17]1[CH:22]=NN=[CH:19][N:18]=1>O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]1[C:12]([Si:13]([CH3:15])([CH3:14])[CH3:16])=[CH:19][N:18]=[N:17][CH:22]=1

Participants

4

Reactant 2

HCID 92631,2,4,5-TetrazineHCID 12687357((2-Fluoro-5-nitrophenyl)ethynyl)trimethylsilane

Product 1

HCID 223295324-(2-Fluoro-5-nitrophenyl)-5-trimethylsilanylpyridazine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(2-Fluoro-5-nitrophenylethynyl)trimethylsilane (8.8 g, 37.1 mmol) and 1,4-dioxane were added to a solution of 1,2,4,5-tetrazine (35 ml, 18.6 mmol, 0.53 M in dichloromethane). The dichloromethane was distilled off and the dioxane solution was stirred at reflux for 36 hours. The solvent was removed to leave a brown oil. Purification by chromatography on silica gel eluting with dichloromethane, then with dichloromethane containing 1% methanol, gave 4-(2-fluoro-5-nitrophenyl)-5-trimethylsilanylpyridazine as a brown oil: m/z (ES+) 292 (M++H) and 249 (M+-3CH2).

Workup

  1. distillationThe dichloromethane was distilled off
  2. temperatureat reflux for 36 hours
  3. customThe solvent was removed
  4. customto leave a brown oil
  5. customPurification by chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-bf51ce9ee5b54e588c2183c6c9a7c3a5
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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