Water → 4-(2-Difluoromethoxypyridin-4-Yloxy)-2-(Pyrazin-2-yl)-Pyrimidine

HRID 411832

反応式

HRID 411832 の反応式
O.Cl[C:3](Cl)(Cl)[CH2:4][CH:5](Cl)OCC.Cl.[N:13]1[CH:18]=[CH:17][N:16]=[CH:15][C:14]=1[C:19]([NH2:21])=[NH:20].[F:22][CH:23]([F:32])[O:24][C:25]1[CH:30]=[C:29]([OH:31])[CH:28]=[CH:27][N:26]=1.C(=O)([O-])[O-].[K+].[K+].ClC(Cl)=CC=O>C(COC)OC.Cl.N1C=CN=CC=1C(N)=N>[F:32][CH:23]([F:22])[O:24][C:25]1[CH:30]=[C:29]([O:31][C:3]2[CH:4]=[CH:5][N:21]=[C:19]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][N:13]=3)[N:20]=2)[CH:28]=[CH:27][N:26]=1

参加物

9

反応物 6

HCID 962WaterHCID 11430Potassium CarbonateHCID 175543,3-Dichloro-2-propenalHCID 470895Pyrazine-2-carboxamidine hydrochlorideHCID 123508221,1,1,3-Tetrachloro-3-ethoxypropaneHCID 178516524HCID 178516524、化合物

生成物 1

HCID 97970114-(2-Difluoromethoxypyridin-4-Yloxy)-2-(Pyrazin-2-yl)-Pyrimidine収率 82%

試薬・触媒・溶媒 2

HCID 470895Pyrazine-2-carboxamidine hydrochloride触媒HCID 80711,2-Dimethoxyethane溶媒2 回

反応条件

温度
60 °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 60° C. The resulting mixture is slowly added to a mixture consisting of a pyrazine-2-carboxamidine hydrochloride (10 mmoles). 2-difluoromethoxypyridin-4-ol (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 pyrazine-2-carboxamidine hydrochloride (0.5 mmoles) is added. The reaction mixture is stirred for 2 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 chromatograph on SiO2 (ethyl acetate) to yield 2,60 g (82%) of beige crystals having a melting point of 128-129° C.

後処理

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

出典と根拠

ORDレコード
ord-fe20903884244f7cb91403e02874d742
出典データセット
uspto-grants-2003_05
特許番号
US06559307B2

関連ノート

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