Water → HCID 89689581, compound

HRID 1774940Notes

Reaction equation

HRID 1774940 reaction equation
Br[C:2]1[N:3]=[C:4]([O:9][CH3:10])[C:5]([NH2:8])=[N:6][CH:7]=1.N1C=CC=[CH:13][CH:12]=1.C(B1OB(C=C)OB(C=C)O1)=C.C(=O)([O-])[O-].[K+].[K+].O>C(COC)OC.O>[CH3:10][O:9][C:4]1[C:5]([NH2:8])=[N:6][CH:7]=[C:2]([CH:12]=[CH2:13])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27348062,4,6-Trivinylboroxin-Pyridine ComplexHCID 113447242-Amino-5-bromo-3-methoxypyrazine

Product 1

HCID 89689581HCID 89689581, compound

Reagents, catalysts & solvents 1

HCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

A mixture of 5-bromo-3-methoxypyrazin-2-amine (800 mg, 3.92 mmol, 1 eq.; Jiang, B. et al. Bioorg. Med. Chem. (2001), 9, 1149-1154.), trivinylboroxine pyridine-complex (944 mg, 3.92 mmol, 1.0 eq), tetrakis(triphenylphosphin)palladium(0) (45 mg, 0.04 mmol, 0.01 eq) and potassium carbonate (542 mg, 3.92 mmol, 1.0 eq) in 40 mL dimethoxyethane/water (3/1) was stirred at room temperature for 10 min and then heated to reflux temperature for 3 hours. The reaction mixture was hydrolysed with 100 mL of water and extracted with ethyl acetate. The resulting organic phase was washed with brine, dried with sodium sulphate and concentrated in vacuo. The crude mixture was purified via MPLC (column: Snap cartridge, eluent: hexane→hexane/ethyl acetate 1/1) to deliver 495 mg (78%) of the title compound.

Workup

  1. temperatureheated
  2. temperatureto reflux temperature for 3 hours
  3. extractionextracted with ethyl acetate
  4. washThe resulting organic phase was washed with brine
  5. dry with materialdried with sodium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe crude mixture was purified via MPLC (column: Snap cartridge, eluent: hexane→hexane/ethyl acetate 1/1)

Sources & evidence

ORD record
ord-d6286732ffe94ca39c599a813bcb012b
Source dataset
uspto-grants-2016_02
Patent number
US09260435B2

Reaction notes

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