Sodium borohydride → 2-Hydroxymethyl-1-methyl-4-phenyl-5-(4-pyridyl)imidazole

HRID 1387644Notes

Reaction equation

HRID 1387644 reaction equation
[CH:1]([C:3]1[N:4]([CH3:20])[C:5]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[N:4]([CH3:20])[C:5]([C:14]2[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=2)=[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 187715342-Formyl-1-methyl-4-phenyl-5-[4-pyridyl]imidazole

Product 1

HCID 187715292-Hydroxymethyl-1-methyl-4-phenyl-5-(4-pyridyl)imidazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-formyl-1-methyl-4-phenyl-5-[4-pyridyl]imidazole (0.830 g, 3.15 mmol) in MeOH at 0° C. was added NaBH4 (0.143 g, 3.78 mmol). The mixture was stirred at rt for 0.5 h when the solvent was evaporated in vacuo and the residue was partitioned between CH2Cl2 and H2O. The organic extract was washed with aqueous NaCl and dried (MgSO4). The solvent was removed in vacuo and the residue was purified by flash chromatography eluting with 25:1 CH2Cl2/MeOH. The title compound was obtained as a white solid (0.608 g, 73%): mp 236-238° C.

Workup

  1. customwas evaporated in vacuo
  2. customthe residue was partitioned between CH2Cl2 and H2O
  3. extractionThe organic extract
  4. washwas washed with aqueous NaCl
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by flash chromatography
  8. washeluting with 25:1 CH2Cl2/MeOH

Sources & evidence

ORD record
ord-363d3869861a4194af920e4fe3cd6bdd
Source dataset
uspto-grants-2001_07
Patent number
US06268370B1

Reaction notes

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