Potassium Carbonate → HCID 21897234, compound

HRID 719971Notes

Reaction equation

HRID 719971 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][C:5](Br)=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:5]1[N:6]=[CH:7][C:2]([NH2:1])=[N:3][CH:4]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5995392-Amino-5-bromopyrazineHCID 27339582-Methoxyphenylboronic acid

Product 1

HCID 21897234HCID 21897234, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 2-amino-5-bromopyrazine (1.16 g, 6.67 mmol) and 2-methoxyphenylboronic acid (1.17 g, 7.70 mmol) in N,N-dimethylformamide (15 mL) was treated with tetrakis(triphenylphosphine)palladium(0) (193 mg, 0.17 mmol) and potassium carbonate (1.87 g, 13.34 mmol). The mixture was heated at 110° C. overnight. The reaction mixture was extracted with chloroform and water. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 2/1 ethyl acetate/hexanes (2/1 ratio) afforded 5-(2-methoxy-phenyl)-pyrazin-2-ylamine (210 mg, 16%).

Workup

  1. extractionThe reaction mixture was extracted with chloroform and water
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f6eef49d808b4ebca3ab018c86099362
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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