Isopropylamine → 3-Bromo-n-isopropylimidazo[1,2-a]pyrazin-8-amine

HRID 457009Notes

Reaction equation

HRID 457009 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.[CH:12]([NH2:15])([CH3:14])[CH3:13]>C1COCC1.C(Cl)Cl>[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][N:9]=[C:10]([NH:15][CH:12]([CH3:14])[CH3:13])[C:5]2=[N:4][CH:3]=1

Participants

5

Reactant 2

HCID 6363IsopropylamineHCID 142075923,5-Dibromoimidazo[1,2-a]pyrazine

Product 1

HCID 210709143-Bromo-n-isopropylimidazo[1,2-a]pyrazin-8-amineYield 68.1%

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 isopropylamine (1.3 ml, 14.4 mmol). The mixture was heated at 70° C. overnight. The mixture was then cooled to rt, 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 125 mg (yield 68%) of the title compound.

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-ca7f3bdf0e1a4c0e82736dfcd9a0b1a3
Source dataset
uspto-grants-2007_03
Patent number
US07186832B2

Reaction notes

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