Ethanol → HCID 67523950, compound

HRID 659020Notes

Reaction equation

HRID 659020 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)=[C:12]([F:19])[CH:11]=2)[CH:6]=[CH:5][N:4]=1.C(O)C.[H][H]>[Pd].C1COCC1>[F:19][C:12]1[CH:11]=[C:10]([O:9][C:7]2[CH:6]=[CH:5][N:4]=[C:3]([S:2][CH3:1])[N:8]=2)[CH:15]=[CH:14][C:13]=1[NH2:16]

Participants

6

Reactant 3

HCID 702EthanolHCID 67523917HCID 67523917, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67523950HCID 67523950, compoundYield 39.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 570 mg (2.03 mmol) 2-methylsulfanyl-4-(3-fluoro-4-nitrophenoxy)-pyrimidine, 10 ml ethanol, 10 ml THF, and 200 mg 10% palladium/C is hydrogenated at 50 mbar hydrogen pressure at r.t. for 8 h. The catalyst was removed by filtration, washed with 10 ml ethanol and evaporated. The residue was purified by chromatography on silica (ethyl acetate/n-heptane 1:2) to give 200 mg (39%) 2-fluoro-4-(2-methylsulfanyl-pyrimidin-4-yloxy)-phenylamine.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with 10 ml ethanol
  3. customevaporated
  4. customThe residue was purified by chromatography on silica (ethyl acetate/n-heptane 1:2)

Sources & evidence

ORD record
ord-c2d8deeb478e4c12817d5692642a2966
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

Loading…