2-(4,6-Dichloropyrimidin-2-yl)acetonitrile → (Pyrimidin-2-yl)acetonitrile
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
Product 1
Reagents, catalysts & solvents 2
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
- filtrationThe reaction was filtered through celite
- washwashed the celite with MeOH
- concentrationThe combined filtrates were concentrated under reduced pressure
- 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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