Tetrabutylammonium Fluoride → 3-Ethynyl-imidazo[1,2-A]pyrazine

HRID 1260804Notes

Reaction equation

HRID 1260804 reaction equation
C[Si]([C:5]#[C:6][C:7]1[N:11]2[CH:12]=[CH:13][N:14]=[CH:15][C:10]2=[N:9][CH:8]=1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:6]([C:7]1[N:11]2[CH:12]=[CH:13][N:14]=[CH:15][C:10]2=[N:9][CH:8]=1)#[CH:5]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 667356023-((Trimethylsilyl)ethynyl)imidazo[1,2-a]pyrazine

Product 1

HCID 722072723-Ethynyl-imidazo[1,2-A]pyrazineYield 77.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-((Trimethylsilyl)ethynyl)imidazo[1,2-a]pyrazine (0.15 g, 0.7 mmol) in 3.5 mL of THF was added 1.05 mL (1.05 mmol) of tetrabutylammonium fluoride (1.0M in THF) at ambient temperature. The solution was stirred for 15 min, concentrated, and the crude product purified by silica gel flash chromatography (eluted with 50% EtOAc/hexanes) to provide 0.078 g of product.

Workup

  1. concentrationconcentrated
  2. customthe crude product purified by silica gel flash chromatography (eluted with 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b1ca89b1b45a42a8a64f328bd4004742
Source dataset
uspto-grants-2013_06
Patent number
US08470851B2

Reaction notes

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