Dichloromethane → 3-(2-Methyl-pyrimidin-5-yl)-propionic acid methyl ester

HRID 705974Notes

Reaction equation

HRID 705974 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH:4]=[CH:5][C:6]1[CH:7]=[N:8][C:9]([CH3:12])=[N:10][CH:11]=1.C(Cl)Cl>[Pd].C(O)C>[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][C:6]1[CH:7]=[N:8][C:9]([CH3:12])=[N:10][CH:11]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 677728483-(2-Methyl-pyrimidin-5-yl)-acrylic acid methyl ester

Product 1

HCID 677746633-(2-Methyl-pyrimidin-5-yl)-propionic acid methyl esterYield 98.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-(2-Methyl-pyrimidin-5-yl)-acrylic acid methyl ester (450 mg, 2.53 mmol, 1 eq) and Pd/C, 10% (0.05 eq, 135 mg) were stirred in a DCM (4 ml)/ethanol (4 ml) mixture under hydrogen atmosphere at room temperature for 20 minutes. Pd/C was filtered off over a celite pad, the solvent was evaporated and obtained was 3-(2-methyl-pyrimidin-5-yl)-propionic acid methyl ester (450 mg, yield=90%, purity=88%). MS: [M+H]+=181.14 1H NMR (300 MHz; CDCl3) δ/ppm 2.60 (t, d, J=7.66 Hz, 2H), 2.66 (s, 3H), 2.87 (t, J=7.66 Hz, 2H), 3.63 (s, 3H), 8.47 (s, 2H)

Workup

  1. filtrationPd/C was filtered off over a celite pad
  2. customthe solvent was evaporated
  3. customobtained

Sources & evidence

ORD record
ord-56dfb1f2013a4ae788f744012ab90361
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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