Ethyl 3-(pyrimidin-5-yl)prop-2-enoate → Ethyl 3-(5-pyrimidyl)propionate

HRID 2228908Notes

Reaction equation

HRID 2228908 reaction equation
[N:1]1[CH:6]=[C:5]([CH:7]=[CH:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:4]=[N:3][CH:2]=1>C(O)C.[Pd]>[N:1]1[CH:6]=[C:5]([CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:4]=[N:3][CH:2]=1

Participants

4

Reactant 1

HCID 53438539Ethyl 3-(pyrimidin-5-yl)prop-2-enoate

Product 1

HCID 21936199Ethyl 3-(5-pyrimidyl)propionateYield 47.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl 3-(5-pyrimidyl)acrylate (4.75 g) in ethanol (90 ml) was added 5% palladium on charcoal (0.2 g). The mixture was hydrogenated at an initial pressure of 50 psi, then filtered to remove catalyst and the solvent evaporated. Water was added, and the product extracted into ether. Drying, charcoaling and evaporation gave ethyl 3-(5-pyrimidyl)propionate (2.3 g) as a yellow oil. 1H-NMR (CDCl3) δ 1.23 (3H, t), 2.69 (2H, t), 2.96 (2H, t), 4.14 (2H, q), 8.635 (2H, s) and 9.09 (1H, s).

Workup

  1. filtrationfiltered
  2. customto remove catalyst
  3. customthe solvent evaporated
  4. additionWater was added
  5. extractionthe product extracted into ether
  6. customDrying
  7. customcharcoaling and evaporation

Sources & evidence

ORD record
ord-5845df4c4a6b4e97b04c1c946e30da3a
Source dataset
uspto-grants-2002_07
Patent number
US06417192B1

Reaction notes

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