Acetone → HCID 22648768, compound

HRID 393158Notes

Reaction equation

HRID 393158 reaction equation
[CH:1]([C:4]([C:6]1[C:7]([C:12]([F:15])([F:14])[F:13])=[N:8][CH:9]=[N:10][CH:11]=1)=[O:5])([CH3:3])[CH3:2].CC(C)=O>C(O)C>[OH:5][CH:4]([C:6]1[C:7]([C:12]([F:15])([F:14])[F:13])=[N:8][CH:9]=[N:10][CH:11]=1)[CH:1]([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 180AcetoneHCID 22648741HCID 22648741, compound

Product 1

HCID 22648768HCID 22648768, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

25 g (115 mmol) of 5-isopropylcarbonyl-4-trifluorometylpyrimidine was dissolved in 100 ml of ethanol, and under cooling with ice, 6 g (69 mmol) of a borane-tert-butylamine complex was added, followed by stirring for 2 hours. Further, 20 ml of acetone was added, followed by stirring for 0.5 hour. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent/n-hexane:ethyl acetate=1:1) to obtain 22 g (yield: 87%) of 5-(1-hydroxy-2-methylpropyl)-4-trifluoromethylpyrimidine as slightly yellow liquid (nD20=1.4481)

Workup

  1. temperatureunder cooling with ice, 6 g (69 mmol) of a borane-tert-butylamine complex
  2. additionwas added
  3. stirringby stirring for 0.5 hour
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (developing solvent/n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-3ae17014e7cf4fd08e595c793e9019b8
Source dataset
uspto-grants-2004_10
Patent number
US06806230B1

Reaction notes

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