Ethanol → HCID 67523926, compound

HRID 659003Notes

Reaction equation

HRID 659003 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)[CH:6]=[CH:5][N:4]=1.C(O)C.[H][H]>[Pd].C1COCC1>[CH3:1][S:2][C:3]1[N:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)[CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 16654112HCID 16654112, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67523926HCID 67523926, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 120.0 g (456 mmol) 2-methylsulfanyl-4-(4-nitrophenoxy)-pyrimidine, 1200 ml ethanol, 1200 ml THF, and 24.0 g 10% palladium/C is hydrogenated at 46 mbar hydrogen pressure at r.t. for 8 h. The catalyst was removed by filtration, washed with 600 ml ethanol, then 300 ml THF and the combined filtrates evaporated. The residue was dissolved in a mixture of 700 ml ethyl acetate and 300 ml THF. The solution was dried over sodium sulphate and evaporated. The residue was stirred with 250 ml isohexane, the precipitate isolated and washed with 400 ml isohexane. Drying in vacuum at r.t. gave 102.5 g (96%) 4-(2-Methylsulfanyl-pyrimidin-4-yloxy)-phenylamine.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with 600 ml ethanol
  3. custom300 ml THF and the combined filtrates evaporated
  4. dissolutionThe residue was dissolved in a mixture of 700 ml ethyl acetate and 300 ml THF
  5. dry with materialThe solution was dried over sodium sulphate
  6. customevaporated
  7. customthe precipitate isolated
  8. washwashed with 400 ml isohexane
  9. customDrying in vacuum at r.t.

Sources & evidence

ORD record
ord-7574422f682245738ebe97e71eba5cda
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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