Ethylamine → 3-Bromo-N-ethylimidazo[1,2-a]pyrazin-8-amine

HRID 457007Notes

Reaction equation

HRID 457007 reaction equation
[Br:1][C:2]1[N:6]2[C:7](Br)=[CH:8][N:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[CH2:12]([NH2:14])[CH3:13].C1COCC1>C(Cl)Cl.O>[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][N:9]=[C:10]([NH:14][CH2:12][CH3:13])[C:5]2=[N:4][CH:3]=1

Participants

6

Reactant 3

HCID 6341EthylamineHCID 8028TetrahydrofuranHCID 142075923,5-Dibromoimidazo[1,2-a]pyrazine

Product 1

HCID 103994183-Bromo-N-ethylimidazo[1,2-a]pyrazin-8-amineYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

3,5-Dibromo-imidazo[1,2-a]pyrazine (D) (200 mg, 0.722 mol) was added to 2M ethylamine in THF (10.8 ml, 30 eq.). The mixture was heated at 70° C. in sealed tube for 8 hr. The mixture was then cooled to rt, and diluted with DCM (100 ml) and water (50 ml). The organic layer was washed with brine, dried and concentrated. The residue was purified on a silica gel column to give 92.2 mg (yield 53%) of (3-bromo-imidazo[1,2-a]pyrazin-8-yl)-ethyl-amine as a crystalline solid.

Workup

  1. temperatureThe mixture was then cooled to rt
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-a060667cf24a460ea0905cd3a4e3075e
Source dataset
uspto-grants-2007_03
Patent number
US07186832B2

Reaction notes

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