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

HRID 456121Notes

Reaction equation

HRID 456121 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 in a microwave to 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 silica gel chromatography with EA:Hexanes to provide 6-bromo-N2-(quinolin-6-ylmethyl)pyrazine-2,3-diamine (6.93 g, 92%). 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 silica gel chromatography with EA

Sources & evidence

ORD record
ord-e40dc7c892c34dc88e6b34ebb557bcd2
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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