Water → 5-Methyl-3-nitro-6-(2,2,2-trifluoroethoxy)-2-pyridinamine

HRID 505387Notes

Reaction equation

HRID 505387 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[H-].[Na+].Cl[C:10]1[N:15]=[C:14]([NH2:16])[C:13]([N+:17]([O-:19])=[O:18])=[CH:12][C:11]=1[CH3:20].O>O1CCCC1>[CH3:20][C:11]1[CH:12]=[C:13]([N+:17]([O-:19])=[O:18])[C:14]([NH2:16])=[N:15][C:10]=1[O:4][CH2:3][C:2]([F:6])([F:5])[F:1]

Participants

6

Reactant 4

HCID 962WaterHCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 218373796-Chloro-5-methyl-3-nitropyridin-2-amine

Product 1

HCID 594298145-Methyl-3-nitro-6-(2,2,2-trifluoroethoxy)-2-pyridinamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2,2,2-Trifluoroethanol (340 mg, 3.4 mmol) was dissolved in the tetrahydrofuran (10 ml), sodium hydride (60%) (120 mg, 3.0 mmol) was added thereto, and the reaction mixture was stirred for 30 minutes at room temperature under nitrogen atmosphere. A solution of 6-chloro-5-methyl-3-nitro-2-pyridineamine crude product (400 mg) in tetrahydrofuran (10 ml) was dropped, and the reaction mixture was stirred at room temperature for 2.5 days. Water was added to the reaction solution and extracted with ethyl acetate, and after washed with a sodium bicarbonate solution, dried over magnesium sulfate. The residue obtained by evaporating the solvent was purified by silica gel column chromatography (eluting solvent: ethyl acetate/n-hexane=15/85) to yield the title compound (225 mg, 0.90 mmol) as a yellow solid.

Workup

  1. additionwas added
  2. stirringthe reaction mixture was stirred at room temperature for 2.5 days
  3. extractionextracted with ethyl acetate
  4. washafter washed with a sodium bicarbonate solution
  5. dry with materialdried over magnesium sulfate
  6. customThe residue obtained
  7. customby evaporating the solvent
  8. customwas purified by silica gel column chromatography (eluting solvent: ethyl acetate/n-hexane=15/85)

Sources & evidence

ORD record
ord-e9da3968539f4d7394e371ddd54ec3fc
Source dataset
uspto-grants-2010_08
Patent number
US07781452B2

Reaction notes

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