Pyridine → N-(5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-yl)acetamide

HRID 2389017Notes

Reaction equation

HRID 2389017 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([C:9]#[C:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[C:5]([NH2:8])=[N:6][CH:7]=1.N1C=CC=CC=1.[C:21](Cl)(=[O:23])[CH3:22]>C1COCC1>[Br:1][C:2]1[N:3]=[C:4]([C:9]#[C:10][Si:11]([CH3:13])([CH3:12])[CH3:14])[C:5]([NH:8][C:21](=[O:23])[CH3:22])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 533931895-Bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine

Product 1

HCID 59836029N-(5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-yl)acetamideYield 19%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-Bromo-3-trimethylsilanylethynyl-pyrazin-2-ylamine (2.30 g, 8 mmol) in anhydrous THF (35 ml) and pyridine (1.62 ml, 20.0 mmol) was added acetyl chloride (682 μl, 9.6 mmol). The mixture was stirred at room temperature overnight, and then stirred at 60° C. for 5 hours. Solvents were removed in vacuum and the resulting brown residue was purified by silica gel chromatography with a gradient of ethyl acetate/hexane to afford the title compound (474 mg, 1.52 mmol) as light yellow as off white solid. MS: m/z 311.9/313.9 [MH+].

Workup

  1. stirringstirred at 60° C. for 5 hours
  2. customSolvents were removed in vacuum
  3. customthe resulting brown residue was purified by silica gel chromatography with a gradient of ethyl acetate/hexane

Sources & evidence

ORD record
ord-f3eb7307e8c1450c81eba05101b4ce4d
Source dataset
uspto-grants-2012_09
Patent number
US08268994B2

Reaction notes

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