4-Chloro-2-(methylsulfanyl)-6-(trifluoromethyl)pyrimidine → N-(3-methoxy-1H-pyrazol-5-yl)-2-(methylthio)-6-(trifluoromethyl)pyrimidin-4-amine

HRID 415444

반응식

HRID 415444 반응식
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([S:12][CH3:13])[N:3]=1.Cl.[CH3:15][O:16][C:17]1[NH:21][N:20]=[C:19]([NH2:22])[CH:18]=1>C(O)C>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([NH:22][C:2]2[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([S:12][CH3:13])[N:3]=2)[NH:20][N:21]=1

참가 물질

4

반응물 2

HCID 2480634-Chloro-2-(methylsulfanyl)-6-(trifluoromethyl)pyrimidineHCID 178493289HCID 178493289, 화합물

생성물 1

HCID 66624545N-(3-methoxy-1H-pyrazol-5-yl)-2-(methylthio)-6-(trifluoromethyl)pyrimidin-4-amine수율 21.5%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
90 °C

실험 절차

To a solution of 4-chloro-2-(methylthio)-6-(trifluoromethyl)pyrimidine (2.29 g) in absolute ethanol (50 mL) was added DIEPA (4.4 mL) and 5-methoxy-1H-pyrazol-3-amine hydrogen chloride salt (1.46 g). The resulting solution was heated at 90° C. for over night. The solvent was evaporated under reduced pressure. The crude compound was purified by Gilson (10-60% MeCN/H2O, 15 minutes) to give N-(3-methoxy-1H-pyrazol-5-yl)-2-(methylthio)-6-(trifluoromethyl)pyrimidin-4-amine as solid (0.64 g). m/z 306. N-(3-methoxy-1H-pyrazol-5-yl)-2-(methylthio)-6-(trifluoromethyl)pyrimidin-4-amine (240 mg) was dissolved in methylene chloride (5 mL), MCPBA (529 mg) was added. The resulting solution was stirred at room temperature for 0.5 hours and separate between methylene chloride and saturated sodium carbonate water solution. The organic layer was dried and solvent was removed under reduced pressure and low temperature. The crude product (270 mg) was carried on to do next step without further purification. m/z 338.

후처리

  1. customThe solvent was evaporated under reduced pressure
  2. customThe crude compound was purified by Gilson (10-60% MeCN/H2O, 15 minutes)

출처 및 근거

ORD 기록
ord-a3834143e34d4281a1cb9762b51be000
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088784B2

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