Water → 2-(4-Iodophenoxy)-4-methoxypyrimidine

HRID 1365631

Reaction equation

HRID 1365631 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Cl[C:12]1[N:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][N:13]=1.O>CN(C=O)C>[I:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:12]2[N:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][N:13]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 108944-IodophenolHCID 24758Sodium hydrideHCID 5889352-Chloro-4-methoxypyrimidine

Product 1

HCID 577625592-(4-Iodophenoxy)-4-methoxypyrimidineYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

Under an argon atmosphere, sodium hydride (108 mg) was added to a solution of 4-iodophenol (220 mg) and 2-chloro-4-methoxypyrimidine (168 mg) in anhydrous DMF (10 ml), and the resulting mixture was stirred at 125° C. for 9 hours. The reaction solution was cooled to room temperature and water was added thereto, followed by extracting the resulting mixture with ethyl acetate. Organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by column chromatography (silica gel, eluent: hexane/ethyl acetate=5/1) to obtain 2-(4-iodophenoxy)-4-methoxypyrimidine (312 mg).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionby extracting the resulting mixture with ethyl acetate
  3. washOrganic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter removing anhydrous sodium sulfate
  6. filtrationby filtration
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by column chromatography (silica gel, eluent: hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-b76dc159e5544da2bbe4b8fe799462f0
Source dataset
uspto-grants-2011_02
Patent number
US07893046B2

Linked notes

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