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

HRID 1871859

反応式

HRID 1871859 の反応式
[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]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]

参加物

7

反応物 3

HCID 6328Methyl iodide2 回HCID 6484Dibutyl-zinn [German]HCID 69157115-Methyl-2-thiouridine

生成物 1

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

試薬・触媒・溶媒 3

HCID 67553Tetrabutylammonium Iodide触媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

To a stirred solution of 5-methyl-2-thiouridine (0.500 g, 1.8 mmol) in DMF (10 ml) is added dibutyltin ox-de 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-2-thiouridine.

後処理

  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

出典と根拠

ORDレコード
ord-50a0f4d92613486d9537108a6de20998
出典データセット
uspto-grants-2000_08
特許番号
US06107094

関連ノート

読み込み中…