Sodium borohydride → (3,5-Dimethoxypyrazin-2-yl)methanol

HRID 1609843Notes

Reaction equation

HRID 1609843 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH:11]=[O:12])=[N:5][CH:6]=[C:7]([O:9][CH3:10])[N:8]=1.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[C:4]([CH2:11][OH:12])=[N:5][CH:6]=[C:7]([O:9][CH3:10])[N:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 156968553,5-Dimethoxypyrazine-2-carbaldehyde

Product 1

HCID 22260378(3,5-Dimethoxypyrazin-2-yl)methanolYield 97.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3,5-dimethoxy-pyrazine-2-carbaldehyde (120 mg, 0.71 mmol) in MeOH (8 mL) is added sodium borohydride (40 mg, 1.1 mmol) at 0° C. After the mixture is stirred at this temperature for 0.5 hour, the reaction is quenched with saturated NH4Cl (0.7 mL) and solvent removed in vacuo until dryness. DCM (20 mL) is added, and the solution is dried and solvent removed to give 118 mg of (3,5-dimethoxy-pyrazin-2-yl)-methanol as an oil.

Workup

  1. customthe reaction is quenched with saturated NH4Cl (0.7 mL) and solvent
  2. customremoved in vacuo until dryness
  3. additionDCM (20 mL) is added
  4. customthe solution is dried
  5. customsolvent removed

Sources & evidence

ORD record
ord-1ce326715ca1480e9cbbccefc009728b
Source dataset
uspto-grants-2006_01
Patent number
US06982268B2

Reaction notes

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