HCID 86647419, compound → 4-Methylpyrimidine-2-carbonitrile
Reaction equation
[N:1]1C=CC=N[CH:2]=1.Cl[C:8]1[N:13]=[C:12]([CH3:14])[CH:11]=[CH:10][N:9]=1>CN(C=O)C.CCOC(C)=O.[C-]#N.[Zn+2].[C-]#N>[CH3:14][C:12]1[CH:11]=[CH:10][N:9]=[C:8]([C:2]#[N:1])[N:13]=1Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 110 °C
Procedure
2-chloro-4-methylpyrimidine pyrimidine (725 mg, 5.62 mmol) was combined with zinc cyanide (396 mg, 3.37 mmol) and tetrakis (triphenylphosphne)palladium (0) (716 mg, 0.562 mmol) in DMF (10 mL) and the slurry was heated at 110° C. under nitrogen for 0.5 h. The mixture was cooled to rt, diluted with EtOAc (70 mL) and washed twice with 2N ammonium hydroxide (50 mL). The EtOAc solution was washed with brine (20 mL) and concentrated in vacuo to provide the crude mixture. The crude was then purified by column chromatography (30% EtOAc in hexanes) to afford 4-methylpyrimidine-2-carbonitrile in 67% yield.
Workup
- temperatureThe mixture was cooled to rt
- washwashed twice with 2N ammonium hydroxide (50 mL)
- washThe EtOAc solution was washed with brine (20 mL)
- concentrationconcentrated in vacuo
- customto provide the crude mixture
- customThe crude was then purified by column chromatography (30% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-5b66530fd6f047c3a21c7cc650caaf80
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299267B2
Reaction notes
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