Water → 4-(3-Trifluoromethylphenoxy)-2-(3,5-dimethylpyrazol-1-yl)-pyrimidine

HRID 651734

反応式

HRID 651734 の反応式
O.Cl[C:3](Cl)(Cl)[CH2:4][CH:5](Cl)OCC.[N+]([O-])(O)=O.[CH3:16][C:17]1[CH:21]=[C:20]([CH3:22])[N:19]([C:23]([NH2:25])=[NH:24])[N:18]=1.[F:26][C:27]([F:36])([F:35])[C:28]1[CH:29]=[C:30]([OH:34])[CH:31]=[CH:32][CH:33]=1.C(=O)([O-])[O-].[K+].[K+].ClC(Cl)=CC=O>C(COC)OC.[N+]([O-])(O)=O.CC1C=C(C)N(C(N)=N)N=1>[F:26][C:27]([F:35])([F:36])[C:28]1[CH:29]=[C:30]([CH:31]=[CH:32][CH:33]=1)[O:34][C:3]1[CH:4]=[CH:5][N:25]=[C:23]([N:19]2[C:20]([CH3:22])=[CH:21][C:17]([CH3:16])=[N:18]2)[N:24]=1

参加物

9

反応物 6

HCID 962WaterHCID 73763-(Trifluoromethyl)phenolHCID 11430Potassium CarbonateHCID 175543,3-Dichloro-2-propenalHCID 1981863,5-Dimethyl-1H-pyrazole-1-carboxamidine mononitrateHCID 123508221,1,1,3-Tetrachloro-3-ethoxypropane

生成物 1

HCID 98406254-(3-Trifluoromethylphenoxy)-2-(3,5-dimethylpyrazol-1-yl)-pyrimidine収率 65.8%

試薬・触媒・溶媒 2

HCID 1981863,5-Dimethyl-1H-pyrazole-1-carboxamidine mononitrate触媒HCID 80711,2-Dimethoxyethane溶媒2 回

反応条件

温度
90 °C

実験手順

Water (20 mmoles) is added to a solution of 1,1,1,3-tetrachloro-3-ethoxypropane (10 mmoles) in dimethoxyethane (25 ml). The mixture is stirred for 2 h at 90° C. The resulting mixture is slowly added to a mixture consisting of a 3,5-dimethylpyrazole-1-carboxamidine nitrate (10 mmoles), 3-trifluoromethylphenol (10 mmoles), potassium carbonate (60 mmoles) and dimethoxyethane (50 ml), which is stirred under reflux. When the addition of 3,3-dichloroacrolein solution is completed additional 3,5-dimethylpyrazole-1-carboxamidine nitrate (0.5 mmoles) is added. The reaction mixture is stirred for 10 hours under reflux and subsequently cooled down to ambient temperature, filtered through silica, and the organic phase is concentrated in vacuo. The residue is purified by chromatography on SiO2 (ethyl acetate) to give 2,2 g of a yellow solid. The solid was washed with petrol ether (50 ml) to yield 1,75 g (52%) of colorless crystals having a melting point of 101-102° C.

後処理

  1. additionThe resulting mixture is slowly added to a mixture
  2. stirringis stirred
  3. temperatureunder reflux
  4. additionis added
  5. stirringThe reaction mixture is stirred for 10 hours
  6. temperatureunder reflux
  7. temperaturesubsequently cooled down to ambient temperature
  8. filtrationfiltered through silica
  9. concentrationthe organic phase is concentrated in vacuo
  10. customThe residue is purified by chromatography on SiO2 (ethyl acetate)

出典と根拠

ORDレコード
ord-6034720edf144f68a5a1fdc9f808c53f
出典データセット
uspto-grants-2001_08
特許番号
US06281358B1

関連ノート

読み込み中…