Tert-Butyl hypochlorite → 2-[(4,6-Dimethoxypyrimidin-2-yl)-methylthiomethyl]-6-methoxymethylaniline

HRID 501881

반응식

HRID 501881 반응식
[CH3:1][O:2][CH2:3][C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6].ClOC(C)(C)C.[CH3:17][S:18][CH2:19][C:20]1[N:25]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([O:28][CH3:29])[N:21]=1.C[O-].[Na+]>ClCCl.O.CO>[CH3:27][O:26][C:24]1[CH:23]=[C:22]([O:28][CH3:29])[N:21]=[C:20]([CH:19]([S:18][CH3:17])[C:7]2[CH:8]=[CH:9][CH:10]=[C:4]([CH2:3][O:2][CH3:1])[C:5]=2[NH2:6])[N:25]=1

참가 물질

8

반응물 4

HCID 521297Tert-Butyl hypochloriteHCID 10942334Sodium MethoxideHCID 123343062-(Methoxymethyl)anilineHCID 574281232-Methylthiomethyl-4,6-dimethoxypyrimidine

생성물 1

HCID 167263142-[(4,6-Dimethoxypyrimidin-2-yl)-methylthiomethyl]-6-methoxymethylaniline수율 58.8%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 6344Dichloromethane용매3회

반응 조건

온도
-70 °C

실험 절차

2-Methoxymethylaniline (0.68 g, 4.96 mmol) was dissolved in dichloromethane (50 ml) and the solution was cooled to −70° C. To the cooled solution a solution of tert-butyl hypochlorite (0.54 g, 4.96 mmol) in dichloromethane (1 ml) was added dropwise and the solution was stirred at −70° C. for 10 minutes. To the obtained reaction solution a solution of 2-methylthiomethyl-4,6-dimethoxypyrimidine (0.893 g, 4.46 mmol) in dichloromethane (5 ml) was added dropwise and the solution was stirred at −70° C. for 30 minutes. To the obtained reaction solution a 28% methanol solution of sodium methoxide (4 ml) was added and the solution was stirred until its temperature reached room temperature. Water was added to the reaction solution and the organic layer was separated. The water layer was further extracted twice with dichloromethane. The organic layer was washed with water and dried. Then dichloromethane was distilled off under reduced pressure and the obtained oily substance was purified by column chromatography using 1:6 mixed solvent of ethyl acetate and hexane as eluent to obtain 2-[(4,6-dimethoxypyrimidin-2-yl)-methylthiomethyl]-6-methoxymethylaniline (0.88 g, yield 53%) as oily substance;

후처리

  1. additionwas added dropwise
  2. stirringthe solution was stirred at −70° C. for 30 minutes
  3. additionwas added
  4. stirringthe solution was stirred until its temperature
  5. customreached room temperature
  6. customthe organic layer was separated
  7. extractionThe water layer was further extracted twice with dichloromethane
  8. washThe organic layer was washed with water
  9. customdried
  10. distillationThen dichloromethane was distilled off under reduced pressure
  11. customthe obtained oily substance was purified by column chromatography

출처 및 근거

ORD 기록
ord-8f4ca55198c64fdfb6527531970c3dc7
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772395B2

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