N-bromobutanimide → 3-Bromo-5-chloropyrazin-2-amine

HRID 1713001Notes

Reaction equation

HRID 1713001 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[Br:9]N1C(=O)CCC1=O>ClCCl>[Br:9][C:4]1[C:5]([NH2:8])=[N:6][CH:7]=[C:2]([Cl:1])[N:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 128084192-Amino-5-chloropyrazine

Product 1

HCID 104886093-Bromo-5-chloropyrazin-2-amineYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 250 ml round bottom flask was charged with 5-chloro-pyrazin-2-ylamine (1) (3 g, 23 mmol, N-bromosuccinimide (4 g, 23 mmol) and dichloromethane (100 ml) under nitrogen. The reaction mixture was refluxed for 1 h, then allowed to cool to room temperature and concentrated in vacuo. The compound was purified by flash chromatography, using as eluent pentane/EtOAc 0% to 50%, to give the title compound (3 g, 62 %). 1H NMR (DMSo-d6) 6.8-6.9 (2H, brs), 8.0 (1H, s). MS(ES+): 210, 212.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. concentrationconcentrated in vacuo
  3. customThe compound was purified by flash chromatography

Sources & evidence

ORD record
ord-2c8f5ee4fb2b42c7b65c371b4a8b618a
Source dataset
uspto-grants-2010_09
Patent number
US07795259B2

Reaction notes

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