Diisobutylaluminum hydride → HCID 22260379, compound

HRID 1609833Notes

Reaction equation

HRID 1609833 reaction equation
C[O:2][C:3]([C:5]1[C:10]([O:11][CH3:12])=[N:9][C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][N:6]=1)=O.CC(C[AlH]CC(C)C)C>C1COCC1>[CH3:12][O:11][C:10]1[C:5]([CH2:3][OH:2])=[N:6][CH:7]=[C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:9]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydride2×HCID 235896503-Methoxy-5-phenyl-pyrazine-2-carboxylic acid methyl ester

Product 1

HCID 22260379HCID 22260379, compoundYield 47.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-methoxy-5-phenyl-pyrazine-2-carboxylic acid methyl ester (150 mg, 0.58 mmol) in THF (20 mL) is added DIBAL-H (1 M in DCM, 1 mL, 1 mmol) dropwise at 0° C. under N2. The mixture is stirred at this temperature for 0.5 hour. Another portion of DIBAL-H (1 M in DCM, 0.8 mL, 0.8 mmol) is added. After 0.5 hour, the reaction is quenched with saturated NH4Cl (1 mL), and then NaOH (1.5 M, 2 mL). The mixture is extracted with EtOAc (3×20 mL). The combined organic layers are dried and the solvent removed. The crude product is purified by PTLC (silica gel; 10% MeOH in DCM) to give 60 mg of (3-methoxy-5-phenyl-pyrazin-2-yl)-methanol as an oil.

Workup

  1. waitAfter 0.5 hour
  2. customthe reaction is quenched with saturated NH4Cl (1 mL)
  3. extractionThe mixture is extracted with EtOAc (3×20 mL)
  4. customThe combined organic layers are dried
  5. customthe solvent removed
  6. customThe crude product is purified by PTLC (silica gel; 10% MeOH in DCM)

Sources & evidence

ORD record
ord-4e1363ad939a45068bbcdb22717ea12a
Source dataset
uspto-grants-2006_01
Patent number
US06982268B2

Reaction notes

Loading…