Bromine → HCID 178461599, 화합물

HRID 522808노트

반응식

HRID 522808 반응식
[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[N:16]=[C:15]2[C:11]([N:12]=[CH:13][NH:14]2)=[C:10]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][C@H:18]2[CH3:23])[N:9]=1.[Br:24]Br.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[Br:24][C:13]1[NH:14][C:15]2[C:11]([N:12]=1)=[C:10]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][C@H:18]1[CH3:23])[N:9]=[C:8]([N:3]1[CH2:4][CH2:5][O:6][CH2:7][C@@H:2]1[CH3:1])[N:16]=2

참가 물질

5

반응물 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 178461602HCID 178461602, 화합물

생성물 1

HCID 178461599HCID 178461599, 화합물수율 46.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

2-((S)-3-Methyl-morpholin-4-yl)-6-((R)-3-methyl-morpholin-4-yl)-9H-purine (786 mg, 2.47 mmol) were dissolved in CH2Cl2 (25 mL). Bromine (0.16 mL, 3.09 mmol) diluted in 2 mL of CH2Cl2 was added slowly within 2 minutes. The reaction mixture was stirred for 6 hours at room temperature. Aqueous Na2S2O3 (10 mL) was added to the reaction mixture, and stirring was continued for 15 minutes. The organic layer was washed with brine and aqueous NaHCO3. Drying over Na2SO4, filtering and concentration under reduced pressure gave a residue, which was purified by column chromatography (40 g SiO2, heptane/EtOAc in a gradient from 2/3 to 4/1) to give the product as a foam (455 mg, 46%).

후처리

  1. additionwas added slowly within 2 minutes
  2. stirringstirring
  3. waitwas continued for 15 minutes
  4. washThe organic layer was washed with brine and aqueous NaHCO3
  5. dry with materialDrying over Na2SO4
  6. filtrationfiltering
  7. concentrationconcentration under reduced pressure
  8. customgave a residue, which
  9. customwas purified by column chromatography (40 g SiO2, heptane/EtOAc in a gradient from 2/3 to 4/1)

출처 및 근거

ORD 기록
ord-70166902903642bb9a305b9a8fe17d50
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334271B2

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