Dimethylformamide → 3-(5-Bromo-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-benzonitrile

HRID 426273ノート

反応式

HRID 426273 の反応式
[Br:1][C:2]1[C:3]([O:11][CH3:12])=[N:4][C:5](Cl)([O:8][CH3:9])[NH:6][CH:7]=1.C([CH2:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([CH3:24])[CH:23]=1)[C:19]#[N:20])#N.[H-].[Na+].CN(C)C=[O:30]>>[Br:1][C:2]1[C:7]([C:15]([C:16]2[CH:17]=[C:18]([CH:21]=[C:22]([CH3:24])[CH:23]=2)[C:19]#[N:20])=[O:30])=[N:6][C:5]([O:8][CH3:9])=[N:4][C:3]=1[O:11][CH3:12]

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydride2 回HCID 667054463-(Cyanomethyl)-5-methylbenzonitrileHCID 178494207HCID 178494207、化合物

生成物 1

HCID 591847973-(5-Bromo-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-benzonitrile

反応条件

温度
0 °C

実験手順

5-Bromo-2-chloro-2,4-dimethoxy-pyrimidine (980 mg, 3.87 mmol) and 3-cyanomethyl-5-methyl-benzonitrile (666.4 mg, 4.26 mmol) were dissolved in dimethyl formamide (10 mL) at room temperature. The solution was cooled to 0° C. Sodium hydride in mineral oil (60%, 170 mg, 4.26 mmol) was added, the reaction mixture was allowed to warm to room temperature and stirring was continued. After 18 hours, a second batch of sodium hydride suspension in mineral oil (60%, 170 mg, 4.26 mmol) was added and stirring was continued for 30 minutes. The reaction was placed under an atmosphere of oxygen and stirring at room temperature was continued. After 72 hours, the reaction was quenched with aqueous ammonium chloride solution and extracted with diethyl ether. The combined organic layers were dried over sodium sulfate. Filtration and evaporation of solvents yielded the crude material. The crude material was purified by flash chromatography on silica gel (eluent: ethyl acetate in hexanes) to yield the product (445 mg, 1.23 mmol). 1H (CDCl3): δ=7.93 (s, 1H), 7.87 (s, 1H), 7.70 (s, 1H), 4.13 (s, 3H), 3.98 (s, 3H), 2.46 (s, 3H) ppm.

後処理

  1. temperatureto warm to room temperature
  2. stirringstirring
  3. waitwas continued for 30 minutes
  4. stirringstirring at room temperature
  5. waitAfter 72 hours
  6. customthe reaction was quenched with aqueous ammonium chloride solution
  7. extractionextracted with diethyl ether
  8. dry with materialThe combined organic layers were dried over sodium sulfate
  9. filtrationFiltration and evaporation of solvents
  10. customyielded the crude material
  11. customThe crude material was purified by flash chromatography on silica gel (eluent: ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-17bc7535f4fc4627b50385d198a8b61f
出典データセット
uspto-grants-2012_01
特許番号
US08106064B2

反応ノート

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