Sodium Hydroxide → [3-(5-Methylpyrimidin-2-yl)phenyl]methanol

HRID 2088404Notes

Reaction equation

HRID 2088404 reaction equation
[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].[CH3:6][C:7]1[CH:8]=[N:9][C:10]([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=2)[C:16](OC)=[O:17])=[N:11][CH:12]=1.[OH-].[Na+]>C1COCC1.ClCCl.O>[CH3:6][C:7]1[CH:12]=[N:11][C:10]([C:13]2[CH:14]=[C:15]([CH2:16][OH:17])[CH:20]=[CH:21][CH:22]=2)=[N:9][CH:8]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 59484867Methyl 3-(5-methylpyrimidin-2-yl)benzoate

Product 1

HCID 59484945[3-(5-Methylpyrimidin-2-yl)phenyl]methanol

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

600 mg (5.41 mmol) of powdered calcium chloride are added to a suspension of 400 mg (10.6 mmol) of sodium borohydride in 20 ml of THF, and the mixture is stirred at room temperature for 1.5 hours. A solution of 751 mg (3.29 mmol) of methyl 3-(5-methylpyrimidin-2-yl)benzoate in 10 ml of THF is added dropwise to this suspension with stirring, and the mixture is stirred at room temperature for 18 hours. 10 ml of 1 N NaOH, water and dichloromethane are added to the reaction mixture, which is then filtered. The organic phase of the filtrate is separated off, dried over sodium sulfate and evaporated. The residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent: [3-(5-methylpyrimidin-2-yl)phenyl]methanol as colourless solid; LCMS 201.

Workup

  1. stirringwith stirring
  2. stirringthe mixture is stirred at room temperature for 18 hours
  3. filtrationis then filtered
  4. customThe organic phase of the filtrate is separated off
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent

Sources & evidence

ORD record
ord-d1b634644be54ec6a257c51be459d27d
Source dataset
uspto-grants-2013_05
Patent number
US08435986B2

Reaction notes

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