Triethylamine → 6-bromo-N2-(quinolin-6-ylmethyl)pyrazine-2,3-diamine

HRID 1892345Notes

Reaction equation

HRID 1892345 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][NH2:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Br[C:14]1[C:15]([NH2:21])=[N:16][CH:17]=[C:18]([Br:20])[N:19]=1.C(N(CC)CC)C>C(Cl)Cl.O>[Br:20][C:18]1[N:19]=[C:14]([NH:12][CH2:11][C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[N:1]=[CH:2][CH:3]=[CH:4]3)[C:15]([NH2:21])=[N:16][CH:17]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 6200042-Amino-3,5-dibromopyrazineHCID 15143846-(Aminomethyl)quinoline

Product 1

HCID 457894186-bromo-N2-(quinolin-6-ylmethyl)pyrazine-2,3-diamineYield 92.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of quinolin-6-ylmethanamine (3.6 g, 22.76 mmol), 3,5-dibromopyrazin-2-amine (5.75 g, 22.76 mmol) and triethyl amine (4.61 g, 45.5 mmol) was heated with microwave irradiation at 130° C. for 5 h. The reaction mixture was diluted with CH2Cl2 and water and the organic layer was separated, washed with aqueous NH4Cl, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography with EtOAc:hexanes to provide 6.93 g (92%) of the title compound. LCMS (method A): [MH]+=330, tR=4.89 min.

Workup

  1. customthe organic layer was separated
  2. washwashed with aqueous NH4Cl
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography with EtOAc

Sources & evidence

ORD record
ord-7a1466829db94f6f95e24c5f411d5702
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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