Tetrahydrofuran → HCID 178518416, compound

HRID 15065Notes

Reaction equation

HRID 15065 reaction equation
C([Li])CCC.[O:6]1CCCC1.Cl[C:12]1[N:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH:15]=[CH:14][N:13]=1>C(OCC)(=O)C.O>[F:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][O:18][C:16]2[CH:15]=[CH:14][NH:13][C:12](=[O:6])[N:17]=2)=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 860707302-Chloro-4-(4-fluorobenzyloxy)pyrimidineHCID 178418339Butyllithium

Product 1

HCID 178518416HCID 178518416, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

n-Butyl lithium (2.6 M n-hexane solution, 7.2 mL) was added to tetrahydrofuran solution (10 mL) of 2-popenyl alcohol (1.8 mL) at −78° C., and stirred at the same temperature for 30 minutes. This reaction liquid was gradually added to tetrahydrofuran solution (20 mL) of 2-chloro-4-(4-fluorobenzyloxy)pyrimidine (4.36 g) and stirred at 60° C. for 4 hours, followed by 24 hours' reflux. Cooling the reaction liquid to room temperature, ethyl acetate was added thereto, followed by washing with water and saturated brine and drying over anhydrous magnesium sulfate. Concentrating the solvent under reduced pressure, the residue was dissolved in tetrahydrofiaan (20 mL). To the solution piperidine (2 mL) and tetrakis(triphenylphosphine)palladium (780 mg) were added and stirred at room temperature for 4 hours. The reaction liquid was added to water (100 mL)-ethyl acetate (50 mL) mixture, and the insoluble matter was recovered by filtration to provide the title compound (0.96 g, 24%).

Workup

  1. customThis reaction liquid
  2. stirringstirred at 60° C. for 4 hours
  3. waitfollowed by 24 hours
  4. temperature' reflux
  5. temperatureCooling
  6. customthe reaction liquid to room temperature
  7. washby washing with water and saturated brine
  8. dry with materialdrying over anhydrous magnesium sulfate
  9. concentrationConcentrating the solvent under reduced pressure
  10. dissolutionthe residue was dissolved in tetrahydrofiaan (20 mL)
  11. additionTo the solution piperidine (2 mL) and tetrakis(triphenylphosphine)palladium (780 mg) were added
  12. stirringstirred at room temperature for 4 hours
  13. customThe reaction liquid
  14. filtrationthe insoluble matter was recovered by filtration

Sources & evidence

ORD record
ord-b0abe6c1416d4a91a9d6df5593f8d3f8
Source dataset
uspto-grants-2010_06
Patent number
US07732456B2

Reaction notes

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