Ethanolamine → HCID 86607831, compound

HRID 646668Notes

Reaction equation

HRID 646668 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([O:11]C)=O)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.[NH2:13][CH2:14][CH2:15][OH:16]>C1COCC1.C(OCC)(=O)C>[NH2:1][C:2]1[C:3]([C:9]([NH:13][CH2:14][CH2:15][OH:16])=[O:11])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1

Participants

5

Reactant 2

HCID 700EthanolamineHCID 227251Methyl 3-Amino-6-bromopyrazine-2-carboxylate

Product 1

HCID 86607831HCID 86607831, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-amino-6-bromo-2-carbomethoxypyrazine (100 mg, 0.4 mmol ) and 2-aminoethanol (500 mg, 8.2 mmol ) in THF (5 mL) was heated at reflux for 2 days. The reaction mixture was cooled, diluted with ethyl acetate (20 mL), washed with water then brine, dried over sodium sulfate, filtered, and concentrated. The oily residue was purified by flash chromatography (silica gel, eluted with ethyl acetate-hexanes gradient from 15% to 80% yield) to give 3-amino-N-(2-hydroxyethyl)-6-bromo-pyrazine-2-carboxamide, a pale yellow oil, (108 mg, 96% yield) MS (EI) for C7H9BrN4O2: 262 (MH+).

Workup

  1. temperatureat reflux for 2 days
  2. temperatureThe reaction mixture was cooled
  3. washwashed with water
  4. dry with materialbrine, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe oily residue was purified by flash chromatography (silica gel, eluted with ethyl acetate-hexanes gradient from 15% to 80% yield)

Sources & evidence

ORD record
ord-4202b8b6ffb94d2a9eb150d6ba416c50
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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