Methylamine → Imidazo(1,2-a)pyrazin-8-amine, 3-bromo-N-methyl-

HRID 457005Notes

Reaction equation

HRID 457005 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.[CH3:12][NH2:13].O1CCCC1>C(Cl)Cl.O>[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][N:9]=[C:10]([NH:13][CH3:12])[C:5]2=[N:4][CH:3]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 142075923,5-Dibromoimidazo[1,2-a]pyrazine

Product 1

HCID 3088360Imidazo(1,2-a)pyrazin-8-amine, 3-bromo-N-methyl-Yield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

3,5-Dibromo-imidazo[1,2-a]pyrazine (D) (2.0 g, 7 mol) was added to 2M methylamine in THF (tetrahydrofuran) (100 ml, 30 eq.). The mixture was heated at 70° C. in sealed tube for 3 hr. The mixture was then cooled to rt, diluted with DCM (200 ml) and water (100 ml). The organic layer was washed with brine, dried and concentrated. The residue was purified on a silica gel column to give (3-bromo-imidazo[1,2-a]pyrazin-8-yl)-methyl-amine (yield 50%).

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-d981d48a5468485a82c72f73bba070d4
Source dataset
uspto-grants-2007_03
Patent number
US07186832B2

Reaction notes

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