Benzylamine → N-Benzyl-3-bromoimidazo[1,2-a]pyrazin-8-amine

HRID 1371366Notes

Reaction equation

HRID 1371366 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]([NH2:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(C(C)C)CC)(C)C>C1COCC1.C(Cl)Cl.O>[CH2:12]([NH:19][C:10]1[C:5]2[N:6]([C:2]([Br:1])=[CH:3][N:4]=2)[CH:7]=[CH:8][N:9]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 142075923,5-Dibromoimidazo[1,2-a]pyrazine

Product 1

HCID 21070918N-Benzyl-3-bromoimidazo[1,2-a]pyrazin-8-amineYield 13.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 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 (9 ml) was added benzylamine (0.393 ml, 3.6 mmol) and diisopropylethylamine (DIPEA) (0.627 ml, 3.6 mmol). The mixture was heated at 70° C. for 3 days. The mixture was then cooled to rt, diluted with DCM and water. The organic layer was washed with brine, dried and concentrated. The residue was purified on a silica gel column to give 30 mg of the title compound.

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-87f87e3af4f9415483c232ffb1786275
Source dataset
uspto-grants-2007_01
Patent number
US07157460B2

Reaction notes

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