Ethylamine hydrochloride → 6-Bromo-4-ethyl-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one

HRID 1890884Notes

Reaction equation

HRID 1890884 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[C:11](Br)=[N:10][C:9]([Br:13])=[CH:8][N:7]=1)=[O:4].[CH:14]([N:17](C(C)C)CC)(C)[CH3:15].Cl.C(N)C>C(#N)C>[Br:13][C:9]1[N:10]=[C:11]2[N:17]([CH2:14][CH3:15])[CH2:2][C:3](=[O:4])[NH:5][C:6]2=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 11198Ethylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 582983072-bromo-N-(3,5-dibromopyrazin-2-yl)acetamide

Product 1

HCID 866446546-Bromo-4-ethyl-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-oneYield 36%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-bromo-N-(3,5-dibromopyrazin-2-yl)acetamide (See Example 4.A) (1 equiv) and diisopropylethylamine (3 equiv) in acetonitrile was added ethanamine hydrochloride (1.05 equiv). The solution was allowed to heat to 70° C. for 30 min. The solution was condensed under reduced pressure and purified using column chromatography (0-75% ethyl acetate in hexanes) to afford the title compound in 36% yield. MS (ESI) m/z 257.5 [M]+, 259.4 [M+2]+.

Workup

  1. customcondensed under reduced pressure
  2. custompurified

Sources & evidence

ORD record
ord-16afdf85ecb247e1bf0d79421715bb09
Source dataset
uspto-grants-2013_08
Patent number
US08507492B2

Reaction notes

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