Triphenylphosphine → HCID 14042135, compound

HRID 446912Notes

Reaction equation

HRID 446912 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][C:5](Br)=[CH:6][N:7]=1.[O:13]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14]1.C([O-])(=O)C.[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1>[NH2:1][C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][C:5]([C:15]2[CH:16]=[CH:17][O:13][CH:14]=2)=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 227251Methyl 3-Amino-6-bromopyrazine-2-carboxylateHCID 517044Potassium AcetateHCID 2734358Furan-3-boronic acid

Product 1

HCID 14042135HCID 14042135, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(Step 8-iv) Methyl 3-amino-6-bromopyrazine-2-carboxylate (700 mg, 3 mmol) was dissolved in dioxane (4 mL) with 3-furan boronic acid (0.36 g, 3.2 mmol), potassium acetate (980 mg 10 mmol) and tetrakispalladium triphenylphosphine (200 mg, 0.17 mmol) in a microwave vessel. Nitrogen was bubbled through for 5 minutes, followed by sealing the vessel and microirradiating the mixture for 20 minutes at 170° C. The reaction mixture was diluted with ethyl acetate/saturated sodium bicarbonate, dried over sodium sulfate, and concentrated to give a solid, which was purified by silica gel column chromatography (0 to 70% EtOAc/hexanes) to give methyl 3-amino-6-(furan-3-yl)pyrazine-2-carboxylate as a solid. This methyl ester was dissolved in THF/MeOH and an aqueous solution of LiOH hydrate (150 mg, 3.6 mmol) was added. The reaction mixture was stirred for 1 hour at room temperature, concentrated to half the volume, and diluted with ethyl acetate/10% aqueous citric acid solution. The organic layer was washed with brine, dried, and concentrated in vacuo to yield 3-amino-6-(furan-3-yl)pyrazine-2-carboxylic acid as a solid (0.46 g, 2.3 mmol, 77% overall yield).

Workup

  1. customNitrogen was bubbled through for 5 minutes
  2. customfor 20 minutes
  3. customat 170° C
  4. additionThe reaction mixture was diluted with ethyl acetate/saturated sodium bicarbonate
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto give a solid, which
  8. customwas purified by silica gel column chromatography (0 to 70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d76eb20c34fb4316bb379911b218f15f
Source dataset
uspto-grants-2013_07
Patent number
US08481538B2

Reaction notes

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