HCID 19074101, compound → HCID 19074113, compound

HRID 964913Notes

Reaction equation

HRID 964913 reaction equation
[C:1]([C:5]1[C:10]([C:11](=[O:19])[C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:9][N:8]=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)C>[C:1]([C:5]1[C:10]([CH:11]([C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=2)[OH:19])=[CH:9][N:8]=[CH:7][N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 19074101HCID 19074101, compound

Product 1

HCID 19074113HCID 19074113, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1 g of 4-t-butyl-5-(4-chlorobenzoyl)pyrimidine was dissolved in 20 ml of ethanol, and 0.8 g of a borane ammonia complex was added. The mixture was heated at 50° C.-60° C. for 1 hour, and further refluxed under heating for 30 minutes. After the solvent was distilled off under reduced pressure, water was added, and extraction with chloroform was carried out. The extract layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 0.6 g of the desired product as a viscous liquid. nD20.2 1.5474

Workup

  1. addition0.8 g of a borane ammonia complex was added
  2. temperatureThe mixture was heated at 50° C.-60° C. for 1 hour
  3. temperaturefurther refluxed
  4. temperatureunder heating for 30 minutes
  5. distillationAfter the solvent was distilled off under reduced pressure, water
  6. additionwas added
  7. extractionextraction with chloroform
  8. washThe extract layer was washed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-ab53469e483141ac9856e178c7e13e6b
Source dataset
uspto-grants-1998_06
Patent number
US05773388

Reaction notes

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