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Water → HCID 14648844, compound

HRID 1164718
Notes
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Reaction equation

HRID 1164718 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6228
Dimethylformamide
Solvent

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-d93e880866024e78929e6c02ac9b2dc5
Source dataset
uspto-grants-1990_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04906285

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes