Potassium Carbonate → 5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)-1-pyrimidin-5-ylpyridazin-4(1H)-one

HRID 1528081ノート

反応式

HRID 1528081 の反応式
[CH3:1][O:2][C:3]1[C:4]([OH:20])=[C:5]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:12]=[CH:11][CH:10]=2)[N:6]=[N:7][CH:8]=1.Br[C:22]1[CH:23]=[N:24][CH:25]=[N:26][CH:27]=1.C(=O)([O-])[O-].[K+].[K+].COC1C2C(=C3C(=CC=2)C(OC)=CC=N3)N=CC=1.C(=O)([O-])O.[Na+]>CS(C)=O.[Cu]I>[CH3:1][O:2][C:3]1[C:4](=[O:20])[C:5]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:12]=[CH:11][CH:10]=2)=[N:6][N:7]([C:22]2[CH:23]=[N:24][CH:25]=[N:26][CH:27]=2)[CH:8]=1

参加物

8

反応物 5

HCID 11430Potassium CarbonateHCID 783445-BromopyrimidineHCID 516892Sodium BicarbonateHCID 104622984,7-Dimethoxy-1,10-phenanthrolineHCID 178493808HCID 178493808、化合物

生成物 1

HCID 866865625-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)-1-pyrimidin-5-ylpyridazin-4(1H)-one収率 8.5%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
110 °C

実験手順

A suspension of 5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4-ol (100 mg), 5-bromopyrimidine (119 mg), potassium carbonate (155 mg), copper(I) iodide (14 mg) and 4,7-dimethoxy-1,10-phenanthroline (20 mg) in DMSO (2 mL) was stirred at 110° C. for 40 hr under an argon atmosphere. To the reaction mixture was added aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate/methanol), and recrystallized from ethyl acetate/hexane to give the title compound (11 mg).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by basic silica gel column chromatography (ethyl acetate/methanol)
  5. customrecrystallized from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-03ca3c2730494129871804e15e761e0c
出典データセット
uspto-grants-2015_07
特許番号
US09090586B2

反応ノート

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