Methyl 5-(benzyloxy)-3-methyl-2-(propan-2-yloxy)pyridine-4-carboxylate → Methyl 5-hydroxy-3-methyl-2-(propan-2-yloxy)pyridine-4-carboxylate

HRID 577583Notes

Reaction equation

HRID 577583 reaction equation
C([O:8][C:9]1[C:10]([C:20]([O:22][CH3:23])=[O:21])=[C:11]([CH3:19])[C:12]([O:15][CH:16]([CH3:18])[CH3:17])=[N:13][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[C:10]([C:20]([O:22][CH3:23])=[O:21])=[C:11]([CH3:19])[C:12]([O:15][CH:16]([CH3:17])[CH3:18])=[N:13][CH:14]=1

Participants

4

Reactant 1

HCID 86723809Methyl 5-(benzyloxy)-3-methyl-2-(propan-2-yloxy)pyridine-4-carboxylate

Product 1

HCID 86723810Methyl 5-hydroxy-3-methyl-2-(propan-2-yloxy)pyridine-4-carboxylateYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl 5-(benzyloxy)-3-methyl-2-(propan-2-yloxy)pyridine-4-carboxylate (131b, 1.1 g, 3.5 mmol) and Pd/C (0.5 g) in MeOH (60 mL) was hydrogenated under an H2 balloon at room temperature for 2 hours. The reaction mixture was filtered through CELITE® and the filtrate was concentrated under vacuum to give methyl 5-hydroxy-3-methyl-2-(propan-2-yloxy)pyridine-4-carboxylate (131c, 0.7 g, 89%) as yellow oil.

Workup

  1. customat room temperature
  2. customfor 2 hours
  3. filtrationThe reaction mixture was filtered through CELITE®
  4. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-19c2cda567c54fc3a5de55ee58b37858
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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