methyl (2E)-3-(pyrimidin-5-yl)prop-2-enoate → Methyl 3-(pyrimidin-5-yl)propanoate

HRID 705788Notes

Reaction equation

HRID 705788 reaction equation
[N:1]1[CH:6]=[C:5](/[CH:7]=[CH:8]/[C:9]([O:11][CH3:12])=[O:10])[CH:4]=[N:3][CH:2]=1>CO.[Pd]>[N:1]1[CH:6]=[C:5]([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:4]=[N:3][CH:2]=1

Participants

4

Reactant 1

HCID 18470237methyl (2E)-3-(pyrimidin-5-yl)prop-2-enoate

Product 1

HCID 18470121Methyl 3-(pyrimidin-5-yl)propanoateYield 92.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of methyl (2E)-3-(5-pyrimidinyl)-2-propenoate (19.2 g, 117 mmol) and Pd/C (2 g, 1.879 mmol) in methanol (100 mL) was stirred under H2 at 50° C. overnight. The mixture was filtered through a pad of celite and concentrated to give the crude title compound as yellow oil (18 g, 55.6% yield). LCMS: rt=1.11 min, [M+H+]=167

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-5be687788e274b2cbeacf87c7879ea31
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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