HCID 18650253, compound → Thymine

HRID 1613136Notes

Reaction equation

HRID 1613136 reaction equation
[Si](O[C@@H]1[C@@](CI)(CO)O[C@@H]([N:18]2[CH:26]=[C:24]([CH3:25])[C:22](=[O:23])[NH:21][C:19]2=[O:20])C1)(C(C)(C)C)(C)C.[Si](O[C@@H]1[C@@](C)(CO)O[C@@H](N2C=C(C)C(=O)NC2=O)C1)(C(C)(C)C)(C)C>[OH-].[Na+].CO.[Pd]>[NH:18]1[CH:26]=[C:24]([CH3:25])[C:22](=[O:23])[NH:21][C:19]1=[O:20]

Participants

6

Reactant 2

HCID 18650253HCID 18650253, compoundHCID 18650255HCID 18650255, compound

Product 1

HCID 1135Thymine

Reagents, catalysts & solvents 3

HCID 14798Sodium HydroxideCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of the 4'-α and 4'-β isomers of 3'-O-t-butyldimethylsilyl-4'-iodomethylthymidine (26 mg, 0.05 mM), prepared, e.g., as described in Preparation 6, 10% Pd-C (palladium on carbon) (15 mg), 1 N NaOH (2 drops) in CH3OH was stirred under hydrogen atmosphere at 25° C. for 66 hours. The solvent was removed by evaporation under vacuum pressure. The residue was purified by flash silica gel chromatography. The column was eluted with CH2Cl2 +5% CH3OH, yielding a mixture of the 4'-α and 4'-β isomers of 3'-O-t-butyldimethylsilyl-4'-methylthymidine (13 mg, 0.035 mM) as a colorless oil. MS 371 (MH)+.

Workup

  1. customThe solvent was removed by evaporation under vacuum pressure
  2. customThe residue was purified by flash silica gel chromatography
  3. washThe column was eluted with CH2Cl2 +5% CH3OH
  4. customyielding

Sources & evidence

ORD record
ord-725f5b7b87674a43942b60216ec64b45
Source dataset
uspto-grants-1993_03
Patent number
US05192749

Reaction notes

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