Sodium Carbonate → 5-(3-Furanyl)-2-pyrazinamine

HRID 720003Notes

Reaction equation

HRID 720003 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][C:5](Br)=[CH:4][N:3]=1.[O:9]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10]1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(O)C.C(OCC)(=O)C.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>[O:9]1[CH:13]=[CH:12][C:11]([C:5]2[N:6]=[CH:7][C:2]([NH2:1])=[N:3][CH:4]=2)=[CH:10]1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 5995392-Amino-5-bromopyrazineHCID 2734358Furan-3-boronic acid

Product 1

HCID 218973795-(3-Furanyl)-2-pyrazinamineYield 92.5%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-amino-5-bromopyrazine (300 mg, 1.724 mmol), tetrakis(triphenylphosphine)palladium(0) (340 mg, 0.294 mmol), furan-3-boronic acid acid (300 mg, 2.681 mmol), and a saturated aqueous sodium carbonate solution (2 mL) in ethylene glycol dimethyl ether (5 mL) and ethanol (5 mL) was heated under reflux for 45 min. The reaction mixture was cooled, diluted with ethyl acetate, and washed with water and a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica, 2/3 hexanes/ethyl acetate to ethyl acetate) afforded 5-furan-3-yl-pyrazin-2-ylamine (256.9 mg, 92.5%) as a yellow solid: LRMS for C8H7N3O (M+H)+ at m/z=162.

Workup

  1. temperatureunder reflux for 45 min
  2. temperatureThe reaction mixture was cooled
  3. washwashed with water
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e5159bcfc6874165bc4fb204ce325ddf
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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