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

HRID 1865816

Reaction equation

HRID 1865816 reaction equation
[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]

Participants

7

Reactant 3

HCID 6328Methyl iodide2×HCID 61221Dibutyltin oxideHCID 69157115-Methyl-2-thiouridine

Product 1

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

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

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-2-thiouridine.

Workup

  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

Sources & evidence

ORD record
ord-f13ab420575a4021ae2b4bc0fc076a0f
Source dataset
uspto-grants-2009_12
Patent number
US07629321B2

Linked notes

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