Phosphoric Acid → 7-bromo-1-ethyl-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one

HRID 2200318Notes

Reaction equation

HRID 2200318 reaction equation
Br[C:2]1[C:3]([NH:9][CH2:10][C:11]([OH:13])=O)=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.[CH2:14]([NH2:16])[CH3:15].P(=O)(O)(O)O>O>[Br:8][C:6]1[N:7]=[C:2]2[N:16]([CH2:14][CH3:15])[C:11](=[O:13])[CH2:10][NH:9][C:3]2=[N:4][CH:5]=1

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 6341EthylamineHCID 86654274HCID 86654274, compound

Product 1

HCID 866542757-bromo-1-ethyl-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

The 2-((3,5-dibromopyrazin-2-yl)amino)acetic acid and ethylamine (4 equiv, 70 wt % solution) were combined in water and the mixture was stirred at 90° C. The reaction mixture was cooled to 80° C. and treated with phosphoric acid (4 equiv), and the mixture was cooled to room temperature and the solids were collected by filtration. The product was dried to obtain 7-bromo-1-ethyl-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one as a solid. MS (ESI) m/z 256.9

Workup

  1. temperatureThe reaction mixture was cooled to 80° C.
  2. temperaturethe mixture was cooled to room temperature
  3. filtrationthe solids were collected by filtration
  4. customThe product was dried

Sources & evidence

ORD record
ord-26f8eea241ad4bcaa31c057b6ab5b856
Source dataset
uspto-grants-2016_06
Patent number
US09359364B2

Reaction notes

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