Ammonium Hydroxide → 8-Amino-3-bromoimidazo[1,2-a]pyrazine

HRID 457006Notes

Reaction equation

HRID 457006 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.[NH4+:12].[OH-]>C1COCC1.C(Cl)Cl.Cl>[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][N:9]=[C:10]([NH2:12])[C:5]2=[N:4][CH:3]=1

Participants

6

Reactant 2

HCID 14923Ammonium Hydroxide2×HCID 142075923,5-Dibromoimidazo[1,2-a]pyrazine

Product 1

HCID 103982908-Amino-3-bromoimidazo[1,2-a]pyrazineYield 50%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3,5-dibromo-imidazo[1,2-a]pyrazine (D) (500 mg, 1.8 mmol) in THF (4 ml) was added NH4OH (4 ml). The mixture was heated at 50° C. in sealed tube overnight. Additional NH4OH (4 ml) was added to the reaction mixture and was heated at 50° C. in sealed tube overnight. The mixture was then cooled to rt, diluted with DCM (200 ml) and 1N HCl (50 ml). The organic layer was washed with 10N NaOH, brine, dried and concentrated. The residue was purified on a silica gel column to afford 190 mg (yield 50%) of 3-bromo-imidazo[1,2-a]pyrazin-8-ylamine.

Workup

  1. temperaturewas heated at 50° C. in sealed tube overnight
  2. temperatureThe mixture was then cooled to rt
  3. washThe organic layer was washed with 10N NaOH, brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-52890d81d31a405ab9012a0121fb2a24
Source dataset
uspto-grants-2007_03
Patent number
US07186832B2

Reaction notes

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