2-Methylpyrimidine-5-carbaldehyde → (2-Methylpyrimidin-5-yl)methanol

HRID 512137Notes

Reaction equation

HRID 512137 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][N:3]=1.[BH4-].[Na+]>CO.O>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 31609702-Methylpyrimidine-5-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 14686706(2-Methylpyrimidin-5-yl)methanolYield 39.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 2-methyl-pyrimidine-5-carbaldehyde (5 g, 41 mmol) in MeOH (100 mL) was added NaBH4 (2.3 g, 61.5 mmol) at 0° C. in portions and the resulting mixture was stirred at room temperature for 1 h. The solvent was removed under reduced pressure to give the remains, which was suspended in H2O (20 mL) and extracted with EtOAc (5×50 ml). The organic layer was dried over Na2SO4 and concentrated to afford the title compound (2 g, yield: 39%). 1H NMR (CDCl3 400 MHz): δ8.64 (s, 2H), 4.72 (s, 2H), 2.73 (s, 3H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto give the remains, which
  3. extractionextracted with EtOAc (5×50 ml)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cdfa72d6011b400da887b8af2ef70f71
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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