Sodium borohydride → (2-Methylpyrimidin-5-yl)methanol

HRID 2200559

Reaction equation

HRID 2200559 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8](O)=[O:9])=[CH:4][N:3]=1.[BH4-].[Na+]>C(O)C>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 136708752-Methylpyrimidine-5-carboxylic acid

Product 1

HCID 14686706(2-Methylpyrimidin-5-yl)methanolYield 70.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-methylpyrimidine-5-carboxylic acid (150 mg, 1.23 mm01) in ethanol (5 mL) was added sodium borohydride (93 mg, 2.46 mmol). The mixture was stirred at room temperature for 3 h. It was quenched with aqueous HCl (2 N, 2 mL), extracted with DCM, dried over sodium sulfate, filtered and concentrated give the yellow oil product (2-methylpyrimidin-5-yl)methanol (95 mg, 62.6%). LCMS MH+ 125.

Workup

  1. customIt was quenched with aqueous HCl (2 N, 2 mL)
  2. extractionextracted with DCM
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0e93240c86804c9f9b069ec1e3872045
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Linked notes

Loading…