3-Methoxyphenol → 4-(3-Methoxy-phenoxy)-6-(4-trifluoromethyl-phenyl)-pyrimidine

HRID 857616Notes

Reaction equation

HRID 857616 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[N:5]=[CH:4][N:3]=1.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=1.[H-].[Na+]>CN(C=O)C>[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=1)[O:26][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 90073-MethoxyphenolHCID 24758Sodium hydrideHCID 167478374-Chloro-6-(4-(trifluoromethyl)phenyl)pyrimidine

Product 1

HCID 103829654-(3-Methoxy-phenoxy)-6-(4-trifluoromethyl-phenyl)-pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 100-mL, round-bottomed flask containing 4-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidine, (Example 2(a), Method A), (0.15 g, 0.58 mmol) and 3-methoxyphenol (0.10 g, 0.81 mmol, Aldrich) in DMF (6 mL), was added NaH (32 mg, 0.81 mmol, 60% in mineral oil, Aldrich) at room temperature The solution was then stirred at room temperature for 4 h. After the solvent was removed in vacuum, EtOAc (10 mL) was added to the residue, and the mixture was washed with water (8 mL), dried over Na2SO4, filtered, and concentrated in vacuum. Silica gel chromatography (5:1 hexanes/EtOAc) afforded the title compound as a white solid. Mp: 87–88° C. MS (ESI, pos. ion) m/z: 347 (M+1). Anal. Calcd for C18H13F3N2O2: C, 62.54; H, 3.75; N, 8.09. Found: C, 62.54; H, 3.75; N, 7.99.

Workup

  1. customAfter the solvent was removed in vacuum, EtOAc (10 mL)
  2. additionwas added to the residue
  3. washthe mixture was washed with water (8 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-08f946cd3d554a2b830fe320de3967d2
Source dataset
uspto-grants-2006_12
Patent number
US07144888B2

Reaction notes

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