2-(4,6-Dichloropyrimidin-2-yl)acetonitrile → (Pyrimidin-2-yl)acetonitrile

HRID 1619192Notes

Reaction equation

HRID 1619192 reaction equation
Cl[C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([CH2:9][C:10]#[N:11])[N:3]=1>CCOC(C)=O.CO.[Pd]>[N:3]1[CH:2]=[CH:7][CH:6]=[N:5][C:4]=1[CH2:9][C:10]#[N:11]

Participants

4

Reactant 1

HCID 2267952-(4,6-Dichloropyrimidin-2-yl)acetonitrile

Product 1

HCID 15264944(Pyrimidin-2-yl)acetonitrileYield 60.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of 2-(4,6-dichloropyrimidin-2-yl)acetonitrile (4.10 g, 21.8 mmol) and TEA (6.07 ml, 43.6 mmol) in EtOAc/MeOH (1/1, 80 mL) was added 10% Pd/C (800 mg) and the solution was vigorously stirred for 2.5 h under H2 atmosphere (1 atm). The reaction was filtered through celite and washed the celite with MeOH. The combined filtrates were concentrated under reduced pressure and purified by flash chromatography (SiO2, 40-6% EtOAc/flexanes, gradient elution) to provide 2-(pyrimidin-2-yl)acetonitrile (1.56 g, 13.1 mmol, 60%) as a pale red liquid.

Workup

  1. filtrationThe reaction was filtered through celite
  2. washwashed the celite with MeOH
  3. concentrationThe combined filtrates were concentrated under reduced pressure
  4. custompurified by flash chromatography (SiO2, 40-6% EtOAc/flexanes, gradient elution)

Sources & evidence

ORD record
ord-a41755a6bec04810bd62305aedce7542
Source dataset
uspto-grants-2014_07
Patent number
US08772296B2

Reaction notes

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