Water → (2-Bromo-3-methylphenyl)(pyrimidin-4-yl)methanol

HRID 1028977Notes

Reaction equation

HRID 1028977 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][N:14]=[C:13](SC)[N:12]=1)=[O:10].O>CCO.[Ni]>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][N:12]=1)[OH:10]

Participants

5

Reactant 2

HCID 962WaterHCID 67325293(2-Bromo-3-methylphenyl)(2-(methylthio)pyrimidin-4-yl)methanone

Product 1

HCID 67324212(2-Bromo-3-methylphenyl)(pyrimidin-4-yl)methanol

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of (2-bromo-3-methylphenyl)(2-(methylthio)pyrimidin-4-yl)methanone (0.10 g, 0.309 mmol) in EtOH (10 mL) was added Raney 2800 nickel, slurry, in water (0.022 mL, 3.41 mmol) and the resulting mixture was reflux until starting material was consumed (2 h). The mixture was brought to RT and decanted. The remaining Ni was extracted with DCM/NH3 (2M in MeOH). The combined organic layers were concentrated and the residue obtained was extracted with DCM and the extracts were combined and concentrated to afford a yellow oil as (2-bromo-3-methylphenyl)(pyrimidin-4-yl)methanol which was used without purification.

Workup

  1. customwas consumed (2 h)
  2. customwas brought to RT
  3. customdecanted
  4. extractionThe remaining Ni was extracted with DCM/NH3 (2M in MeOH)
  5. concentrationThe combined organic layers were concentrated
  6. customthe residue obtained
  7. extractionwas extracted with DCM
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-fa29cff280524d65a83d6afcfc645056
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

Loading…