Ethyl 3-(2-methoxypyrimidin-5-yl)acrylate → Ethyl 3-(2-methoxypyrimidin-5-yl)propionate

HRID 411285Notes

Reaction equation

HRID 411285 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][N:4]=1>C(O)C.C(N(CC)CC)C.[Pd]>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][N:4]=1

Participants

5

Reactant 1

HCID 53940995Ethyl 3-(2-methoxypyrimidin-5-yl)acrylate

Product 1

HCID 21936233Ethyl 3-(2-methoxypyrimidin-5-yl)propionate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

A suspension of ethyl 3-(2-methoxypyrimidin-5-yl)acrylate (52.4 g, 0.252 mol) in ethanol (400 ml) and triethylamine (50 ml) was treated with 10% palladium on carbon (3 g) and hydrogenated at 50 psi for 1.75 h. The catalyst was filtered off through hyflo and the filtrate evaporated. The residue was dissolved in dichloromethane, washed twice with saturated aqueous ammonium chloride, dried (MgSO4) and evaporated to an oil, yield 41.2 g (78%). 1H-NMR (CDCl3) δ1.23 (3H, t), 2.61 (2H, t), 2.87 (2H, t), 3.99 (3H, s), 4.13 (2H, q), 8.39 (2H, s); MS (APCI+) found (M+H)=211; C10H14N2O3 requires 210.

Workup

  1. filtrationThe catalyst was filtered off through hyflo
  2. customthe filtrate evaporated
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed twice with saturated aqueous ammonium chloride
  5. dry with materialdried (MgSO4)
  6. customevaporated to an oil, yield 41.2 g (78%)

Sources & evidence

ORD record
ord-0580867510f1466e9b09bd89e236c93c
Source dataset
uspto-grants-2003_05
Patent number
US06559155B1

Reaction notes

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