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

HRID 411832

반응식

HRID 411832 반응식
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

참가 물질

9

반응물 6

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

생성물 1

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

시약·촉매·용매 2

HCID 470895Pyrazine-2-carboxamidine hydrochloride촉매HCID 80711,2-Dimethoxyethane용매2회

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-fe20903884244f7cb91403e02874d742
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06559307B2

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