Hydrochloric Acid → (4-Pyrimidin-5-ylphenyl)methanol

HRID 1459635Notes

Reaction equation

HRID 1459635 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=2)[CH:4]=[N:3][CH:2]=1.[BH4-].[Na+].Cl.[OH-].[Na+]>CO.CCOC(C)=O.O>[N:1]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH2:11][OH:12])=[CH:13][CH:14]=2)[CH:4]=[N:3][CH:2]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 38612125-(4-Formylphenyl)pyrimidineHCID 4311764Sodium borohydride

Product 1

HCID 7162046(4-Pyrimidin-5-ylphenyl)methanol

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

4-Pyrimidin-5-yl-benzaldehyde (1.89 mmol, 350 mg) was dissolved in MeOH. NaBH4 (9.4 mmol, 357 mg) was added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was cooled to 0° and 9M HCl (0.25 mL) was added dropwise. The reaction mixture was stirred for one half hour. The reaction mixture was then basified with 20% NaOH (pH=10). EtOAc and H2O were added and the layers were separated. The aqueous layer was back extracted with EtOAc (3×). The organic layers were combined, washed with brine, dried (MgSO4), filtered and concentrated to yield a tan solid. Flash chromatography (EtOAc) afforded the title compound as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled to 0°
  2. stirringThe reaction mixture was stirred for one half hour
  3. customthe layers were separated
  4. extractionThe aqueous layer was back extracted with EtOAc (3×)
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto yield a tan solid

Sources & evidence

ORD record
ord-c45debf154334f718e4cd3ad371faa34
Source dataset
uspto-grants-1998_12
Patent number
US05854264

Reaction notes

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