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

HRID 457011Notes

Reaction equation

HRID 457011 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-0624471c96a1412bb63fa365e0423ce3
Source dataset
uspto-grants-2007_03
Patent number
US07186832B2

Reaction notes

Loading…