Sodium borohydride → (3-Chloro-5-methoxy-pyrazin-2-yl)-methanol

HRID 1609848Notes

Reaction equation

HRID 1609848 reaction equation
[Cl:1][C:2]1[C:3]([CH:10]=[O:11])=[N:4][CH:5]=[C:6]([O:8][CH3:9])[N:7]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[C:3]([CH2:10][OH:11])=[N:4][CH:5]=[C:6]([O:8][CH3:9])[N:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 222603943-Chloro-5-methoxypyrazine-2-carbaldehyde

Product 1

HCID 22260387(3-Chloro-5-methoxy-pyrazin-2-yl)-methanolYield 97.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-chloro-5-methoxy-pyrazine-2-carbaldehyde (560 mg, 3.24 mmol) in MeOH (15 mL) is added sodium borohydride (183 mg, 4.83 mmol) at 0° C. After the mixture is stirred at this temperature for 0.5 hour, the reaction is quenched with saturated NH4Cl (1 mL) and solvent removed in vacuo until dryness. DCM (50 mL) is added, and the solution is dried and solvent removed to give 550 mg of (3-chloro-5-methoxy-pyrazin-2-yl)-methanol as an oil.

Workup

  1. customthe reaction is quenched with saturated NH4Cl (1 mL) and solvent
  2. customremoved in vacuo until dryness
  3. additionDCM (50 mL) is added
  4. customthe solution is dried
  5. customsolvent removed

Sources & evidence

ORD record
ord-ac0135374f4541b79b7f76d7026d3c29
Source dataset
uspto-grants-2006_01
Patent number
US06982268B2

Reaction notes

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