Ethanolamine → 2-[(3-Bromoimidazo[1,2-a]pyrazin-8-yl)amino]ethan-1-ol

HRID 1371368

Reaction equation

HRID 1371368 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]([CH2:14][NH2:15])[OH:13]>O1CCOCC1.CC(O)C.C(Cl)Cl.O>[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][N:9]=[C:10]([NH:15][CH2:14][CH2:12][OH:13])[C:5]2=[N:4][CH:3]=1

Participants

6

Reactant 2

HCID 700EthanolamineHCID 142075923,5-Dibromoimidazo[1,2-a]pyrazine

Product 1

HCID 210709042-[(3-Bromoimidazo[1,2-a]pyrazin-8-yl)amino]ethan-1-olYield 33.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 312751,4-DioxaneSolventHCID 21966342Isopropanol methylene chlorideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3,5-dibromo-imidazo[1,2-a]pyrazine (D) (400 mg, 1.44 mmol) in dioxane (2 ml) was added ethanolamine (0.436 ml, 7.22 mmol). The mixture was heated at 80° C. in sealed tube for 5 hr. The mixture was then cooled to rt, diluted with 20% IPA/DCM and water. The organic layer was washed with brine, dried and concentrated. The residue was purified on a silica gel column to give 124 mg (yield 33%) 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-b955da5afce849edb86d9b8793128bff
Source dataset
uspto-grants-2007_01
Patent number
US07157460B2

Linked notes

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