HCID 19074107, compound → HCID 19074109, compound

HRID 964912Notes

Reaction equation

HRID 964912 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:12][N:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13]([CH:14]([OH:19])[C:15]([CH3:17])([CH3:16])[CH3:18])=[CH:12][N:11]=[CH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 19074107HCID 19074107, compound

Product 1

HCID 19074109HCID 19074109, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.2 g of 4-(4-chlorophenyl)-5-pivaloylpyrimidine was dissolved in 20 ml of ethanol, then 1.2 g of a borane ammonia complex was added, and the mixture was stirred at room temperature 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 to obtain 0.8 g of the desired product as a viscous liquid. nD20.2 1.5575

Workup

  1. addition1.2 g of a borane ammonia complex was added
  2. distillationAfter the solvent was distilled off under reduced pressure, water
  3. additionwas added
  4. extractionextraction with chloroform
  5. washThe extract layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-337c275d64ba45e796e4d2e71bf94ef8
Source dataset
uspto-grants-1998_06
Patent number
US05773388

Reaction notes

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