HCID 178470318, compound → HCID 178470319, compound

HRID 869702Notes

Reaction equation

HRID 869702 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][C:12]1[N:13]=[C:14]([CH3:24])[C:15]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:16][C:17]=1[OH:18])C1C=CC=CC=1>C(O)C.[OH-].[Pd+2].[OH-]>[OH:18][C:17]1[N:16]=[C:15]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([CH3:24])=[N:13][C:12]=1[CH2:11][CH2:10][CH2:9][OH:8]

Participants

4

Reactant 1

HCID 178470318HCID 178470318, compound

Product 1

HCID 178470319HCID 178470319, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A suspension of ethyl 5-[3-(benzyloxy)propyl]-6-hydroxy-3-methylpyrazine-2-carboxylate (2.91 g, 8.80 mmol) and palladium hydroxide (1.06 g) in ethanol (60 mL) was refluxed for 7 h. After being cooled to ambient temperature, the reaction mixture was filtrated through celite with ethanol. The filtrate was combined and concentrated in vacuo. The crude was purified by silica gel column chromatography (chloroform to chloroform:methanol=19:1) to give ethyl 6-hydroxy-5-(3-hydroxypropyl)-3-methylpyrazine-2-carboxylate. MS (APCI): m/z 241 (M+H).

Workup

  1. temperaturewas refluxed for 7 h
  2. filtrationthe reaction mixture was filtrated through celite with ethanol
  3. concentrationconcentrated in vacuo
  4. customThe crude was purified by silica gel column chromatography (chloroform to chloroform:methanol=19:1)

Sources & evidence

ORD record
ord-551e9fcc37444811a737c48542d6d01f
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

Loading…