Dimethylformamide → 4-Methoxypyrimidine-2-carbonitrile

HRID 2070968ノート

反応式

HRID 2070968 の反応式
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N:3]=1.[CH3:10][N:11](C=O)C>CCOC(C)=O.[C-]#N.[Zn+2].[C-]#N>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:10]#[N:11])[N:7]=1

参加物

5

反応物 2

HCID 6228DimethylformamideHCID 5889352-Chloro-4-methoxypyrimidine

生成物 1

HCID 132211894-Methoxypyrimidine-2-carbonitrile収率 50%

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

2-chloro-4-methoxypyrimidine (500 mg, 3.45 mmol) was combined with zinc cyanide (242 mg, 2.07 mmol) and tetrakis (triphenylphosphne)palladium (0) (159 mg, 0.14 mmol) in DMF (10 mL) and the slurry was heated at 80° C. under nitrogen for 6 h. The mixture was cooled to rt, diluted with EtOAc (50 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 (10% EtOAc in hexanes) to afford 4-methoxypyrimidine-2-carbonitrile in 50% yield.

後処理

  1. temperatureThe mixture was cooled to rt
  2. washwashed twice with 2N ammonium hydroxide (50 mL)
  3. washThe EtOAc solution was washed with brine (20 mL)
  4. concentrationconcentrated in vacuo
  5. customto provide the crude mixture
  6. customThe crude was then purified by column chromatography (10% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-5652bc9d87534e43b4a20f2015bb210b
出典データセット
uspto-grants-2012_10
特許番号
US08299267B2

反応ノート

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