Ethanol → 2-Chloro-4-(2-methylsulfanyl-pyrimidin-4-yloxy)-phenylamine

HRID 659013Notes

Reaction equation

HRID 659013 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]([Cl:19])[CH:11]=2)[CH:6]=[CH:5][N:4]=1.C(O)C.[H][H]>[Pd].[O-]S([O-])(=O)=O.[Ba+2].C1COCC1>[Cl: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 675239472-Methylsulfanyl-4-(3-chloro-4-nitrophenoxy)-pyrimidineHCID 178418361HCID 178418361, compound

Product 1

HCID 675239652-Chloro-4-(2-methylsulfanyl-pyrimidin-4-yloxy)-phenylamineYield 32.4%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.10 g (3.69 mmol) 2-methylsulfanyl-4-(3-chloro-4-nitrophenoxy)-pyrimidine, 20 ml ethanol, 20 ml THF, and 300 mg palladium/BaSO4 is hydrogenated at 50 mbar hydrogen pressure at r.t. for 8 h. The catalyst was removed by filtration, washed with 20 ml ethanol and evaporated. The residue was purified by chromatography on silica (ethyl acetate/isohexane 2:7) to give 320 mg (32%) 2-chloro-4-(2-methylsulfanyl-pyrimidin-4-yloxy)-phenylamine.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with 20 ml ethanol
  3. customevaporated
  4. customThe residue was purified by chromatography on silica (ethyl acetate/isohexane 2:7)

Sources & evidence

ORD record
ord-96797a2af4a74b7bb8503abd436ae3fd
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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