HCID 19074087, compound → HCID 19074102, compound

HRID 964921Notes

Reaction equation

HRID 964921 reaction equation
B.[Na].[C:3]([C:7]1[C:12]([C:13](=[O:21])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])=[CH:11][N:10]=[CH:9][N:8]=1)([CH3:6])([CH3:5])[CH3:4]>CO>[C:3]([C:7]1[C:12]([CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[OH:21])=[CH:11][N:10]=[CH:9][N:8]=1)([CH3:6])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 19074087HCID 19074087, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 19074102HCID 19074102, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

500 ml of sodium boron hydride (purity 92%) was added to a mixture of 1 g of 4-tert-butyl-5-(2-methylbenzoyl)pyrimidine and 20 ml of dry methanol, under cooling with ice, and the resulting mixture was stirred for 2 hours. The solvent was distilled off under reduced pressure, and to the resulting mixture, ice water and ethyl acetate were added, and the pH was adjusted to a level from 1 to 2 with concentrated hydrochloric acid with stirring. The organic layer was washed with saturated aqueous salt solution twice, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 600 mg of the desired product as white crystals.

Workup

  1. temperatureunder cooling with ice
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionto the resulting mixture, ice water and ethyl acetate were added
  4. stirringwith stirring
  5. washThe organic layer was washed with saturated aqueous salt solution twice
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f47adebeb20e48d6a38326ba203131b2
Source dataset
uspto-grants-1998_06
Patent number
US05773388

Reaction notes

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