methyl (E)-3-(2-methoxy-5-pyrimidinyl)acrylate → Methyl 3-[2-(methyloxy)-5-pyrimidinyl]propanoate

HRID 705791Notes

Reaction equation

HRID 705791 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([O:13][CH3:14])=[O:12])=[CH:5][N:4]=1>CO.[Pd]>[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:7][N:8]=1

Participants

4

Reactant 1

HCID 10774171methyl (E)-3-(2-methoxy-5-pyrimidinyl)acrylate

Product 1

HCID 67776226Methyl 3-[2-(methyloxy)-5-pyrimidinyl]propanoateYield 82.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methyl (2E)-3-[2-(methyloxy)-5-pyrimidinyl]-2-propenoate (24.0 g, 124 mmol) and Pd/C (300 mg) in methanol (250 mL) was stirred at 50° C. under H2 for two days, filtered through a pad of Celite and concentrated to give the title compound as a yellow oil (20 g, 68%), which was used without further purification. LCMS: rt=1.17 min, [M+H+]=196

Workup

  1. filtrationfiltered through a pad of Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-e0d4b6d10d604ff6918b9ed4fce44996
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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