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

HRID 85025Notes

Reaction equation

HRID 85025 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 chloride2×HCID 533931895-Bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine

Product 1

HCID 59836029N-(5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-yl)acetamideYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine (5.0 g, 19 mmol) and pyridine (3.8 mL, 46 mmol) in anhydrous THF (75 mL) was added acetyl chloride (1.6 mL, 23 mmol) in a drop-wise manner. After stirring for 48 hr at rt, additional acetyl chloride (0.4 mL, 6 mmol) was added and the mixture was stirred for an additional 48 hr at rt. The solvent was removed in vacuo, and the residue was diluted with 30% EtOAc in hexanes. The mixture was filtered, and the filtrate was purified via silica gel chromatography eluting with 30% EtOAc in hexanes to give a yellow-brown solid (1.8 g, 31%). 1H NMR (CDCl3, 300 MHz): δ 8.34 (s, 1H), 8.08 (s, 1H), 2.46 (s, 3H), 0.32 (s, 9H). HPLC retention time: 2.29 minutes. MS ESI (m/z): 312.2, 314.2 (M+H)+, calc. 311.

Workup

  1. stirringthe mixture was stirred for an additional 48 hr at rt
  2. customThe solvent was removed in vacuo
  3. additionthe residue was diluted with 30% EtOAc in hexanes
  4. filtrationThe mixture was filtered
  5. customthe filtrate was purified via silica gel chromatography
  6. washeluting with 30% EtOAc in hexanes

Sources & evidence

ORD record
ord-23074e4b33a04c6e84895c824684b7c1
Source dataset
uspto-grants-2014_09
Patent number
US08846909B2

Reaction notes

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