Water → HCID 14648844, compound

HRID 1090298Notes

Reaction equation

HRID 1090298 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([O:10][C:11]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]3[N:32]=[C:31]([O:33][CH3:34])[CH:30]=[C:29]([O:35][CH3:36])[N:28]=3)[C:12]=2[C:13]([O:15]CC[Si](C)(C)C)=[O:14])[N:3]=1.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.S([O-])(O)(=O)=O.[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([O:10][C:11]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]3[N:28]=[C:29]([O:35][CH3:36])[CH:30]=[C:31]([O:33][CH3:34])[N:32]=3)[C:12]=2[C:13]([OH:15])=[O:14])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 516920Potassium bisulfateHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 14648843HCID 14648843, compound

Product 1

HCID 14648844HCID 14648844, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Trimethylsilylethyl 2-(4 chloro 6-methoxypyrimidin-2-yl)oxy-6-(4,6-dimethoxypyrimidin-2-yl)oxybenzoate (4.0 g) was dissolved in 30 ml of DMF. To this solution, tetrabutylammonium fluoride trihydrate (5.9 g) was added, and the mixture was stirred at room temperature for 15 minutes. After completion of the reaction, water and a small amount of an aqueous potassium hydrogen sulfate solution were added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the crystals thereby obtained were washed with a mixture of hexane and IPE to obtain the above identified compound as white crystals (3.2 g). (Melting point: 150-152° C.)

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe crystals thereby obtained
  6. washwere washed with a mixture of hexane and IPE
  7. customto obtain the

Sources & evidence

ORD record
ord-6fcebc8f9f354b29957f8b4fdc47751a
Source dataset
uspto-grants-1992_01
Patent number
US05081244

Reaction notes

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