Butylamine → 3-Bromo-N-butylimidazo[1,2-A]pyrazin-8-amine

HRID 457008Notes

Reaction equation

HRID 457008 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]([NH2:16])[CH2:13][CH2:14][CH3:15]>C1COCC1.C(Cl)Cl>[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][N:9]=[C:10]([NH:16][CH2:12][CH2:13][CH2:14][CH3:15])[C:5]2=[N:4][CH:3]=1

Participants

5

Reactant 2

HCID 8007ButylamineHCID 142075923,5-Dibromoimidazo[1,2-a]pyrazine

Product 1

HCID 210709113-Bromo-N-butylimidazo[1,2-A]pyrazin-8-amineYield 51.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3,5-dibromo-imidazo[1,2-a]pyrazine (D) (200 mg, 0.72 mmol) in THF (3.6 ml) was added butylamine (2.2 ml, 21.6 mmol). The mixture was heated at 70° C. for 3 hr. The mixture was then cooled to rt, and diluted with DCM. The organic layer was washed with water, brine, dried and concentrated. The residue was purified on a silica gel column to afford 99 mg (yield 51%) of (3-bromo-imidazo[1,2-a]pyrazin-8-yl)-butyl-amine.

Workup

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

Sources & evidence

ORD record
ord-81937344802e46d1a69b6365e7092379
Source dataset
uspto-grants-2007_03
Patent number
US07186832B2

Reaction notes

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