HCID 86668092, compound → HCID 86668091, compound

HRID 538390Notes

Reaction equation

HRID 538390 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][C:8]([NH:12][CH2:13][CH:14]([F:16])[F:15])=[C:7]([C:17]#[C:18][Si](C)(C)C)[N:6]=1)=[O:4]>CN(C=O)C.[Cu]I>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]2[CH2:17][CH2:18][N:12]([CH2:13][CH:14]([F:16])[F:15])[C:8]2=[N:9][C:10]=1[NH2:11])=[O:4]

Participants

4

Reactant 1

HCID 86668092HCID 86668092, compound

Product 1

HCID 86668091HCID 86668091, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 3-amino-5-(2,2-difluoro-ethylamino)-6-trimethylsilanylethynyl-pyrazine-2-carboxylic acid methyl ester (624 mg, 1.9 mmol) in DMF (19 ml) was added Copper(I) iodide (181 mg, 0.95 mmol) and the mixture was heated to 120° C. for 2 h. The reaction mixture was filtered through Hyflo, the residue washed with toluene. The combined organic phases were extracted with water, dried with Na2SO4 and evaporated. The residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 40:60) to provide the title compound as yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered through Hyflo
  2. washthe residue washed with toluene
  3. extractionThe combined organic phases were extracted with water
  4. dry with materialdried with Na2SO4
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 40:60)

Sources & evidence

ORD record
ord-fb8b4ac098dd4d579f97f6ec3a1c1ff6
Source dataset
uspto-grants-2014_10
Patent number
US08865712B2

Reaction notes

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