Potassium Iodide → 2-Amino-3-(2-methylbenzylamino)pyrazine

HRID 4294

Reaction equation

HRID 4294 reaction equation
[NH2:1][C:2]1[C:7](Cl)=[N:6][CH:5]=[CH:4][N:3]=1.[CH3:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH2:12][NH2:13].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O.O>[NH2:1][C:2]1[C:7]([NH:13][CH2:12][C:11]2[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=2[CH3:9])=[N:6][CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 69932-MethylbenzylamineHCID 11430Potassium CarbonateHCID 2762242-Amino-3-chloropyrazine

Product 1

HCID 201523282-Amino-3-(2-methylbenzylamino)pyrazineYield 19.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-amino-3-chloropyrazine (4.3 g), 2-methylbenzylamine (4.6 g), potassium carbonate (5.5 g), and potassium iodide (0.4 g) in N,N-dimethylformamide (43 ml) was refluxed for 24 hours under a nitrogen atmosphere and allowed to stand at room temperature. The mixture was poured into water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel (110 g) with a mixture of chloroform and methanol (100:3) as an eluent to give 2-amino-3-(2-methylbenzylamino)pyrazine (1.4 g).

Workup

  1. temperaturewas refluxed for 24 hours under a nitrogen atmosphere
  2. customto stand at room temperature
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (110 g) with a mixture of chloroform and methanol (100:3) as an eluent

Sources & evidence

ORD record
ord-9d28aa19805e4a3182693ceb169ad3c2
Source dataset
uspto-grants-1988_02
Patent number
US04725601

Linked notes

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