Methyl iodide → 2'-O-methyl-5-methyl-2thiouridine

HRID 443326

반응식

HRID 443326 반응식
[CH3:1][C:2]1[C:3](=[O:18])[NH:4][C:5](=[S:17])[N:6]([CH:16]=1)[C@@H:7]1[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[C@H:8]1[OH:9].[CH2:19]([Sn](=O)CCCC)CCC.CI>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH3:19][O:9][C@@H:8]1[C@H:10]([OH:11])[C@@H:12]([CH2:13][OH:14])[O:15][C@H:7]1[N:6]1[CH:16]=[C:2]([CH3:1])[C:3](=[O:18])[NH:4][C:5]1=[S:17]

참가 물질

7

반응물 3

HCID 6328Methyl iodide2회HCID 61221Dibutyltin oxideHCID 69157115-Methyl-2-thiouridine

생성물 1

HCID 186605852'-O-methyl-5-methyl-2thiouridine

시약·촉매·용매 3

HCID 67553Tetrabutylammonium Iodide촉매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

반응 조건

온도
50 °C

실험 절차

To a stirred solution of 5-methyl-2-thiouridine (0.500 g, 1.8 mmol) in DMF (10 ml) is added dibutyltin oxide (0.500 g, 2.0 mmol), tetrabutyl ammonium iodide (0.738 g, 2 mmol), and methyl iodide (1.022 g, 7.2 mmol). The reaction flask is sealed and heated at 50° C. for 16 hours. The mixture is cooled and another portion of methyl iodide is added (1.022 g, 7.2 mmol) and the reaction heated for an additional 16 hours. At the end of this time, the reaction mixture is cooled to room temperature and diluted with methylene chloride and chromatographed using a methylene chloride/methanol gradient. The appropriate fractions are collected and concentrated to give 2'-O-methyl-5-methyl-2thiouridine.

후처리

  1. customThe reaction flask is sealed
  2. temperatureThe mixture is cooled
  3. temperaturethe reaction heated for an additional 16 hours
  4. temperatureAt the end of this time, the reaction mixture is cooled to room temperature
  5. customchromatographed
  6. customThe appropriate fractions are collected
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-44de6741bd8440399f77569d184486d9
출처 데이터셋
uspto-grants-1999_04
특허 번호
US05898031

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