Dimethylformamide → 4-Methoxypyrimidine-2-carbonitrile

HRID 2070968노트

반응식

HRID 2070968 반응식
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

참가 물질

5

반응물 2

HCID 6228DimethylformamideHCID 5889352-Chloro-4-methoxypyrimidine

생성물 1

HCID 132211894-Methoxypyrimidine-2-carbonitrile수율 50%

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-5652bc9d87534e43b4a20f2015bb210b
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299267B2

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