Sodium Iodide → Thymine

HRID 1613135Notes

Reaction equation

HRID 1613135 reaction equation
[Si](O[C@@H]1[C@@](COS(C)(=O)=O)(CO)O[C@@H]([N:22]2[CH:30]=[C:28]([CH3:29])[C:26](=[O:27])[NH:25][C:23]2=[O:24])C1)(C(C)(C)C)(C)C.[Na+].[I-].[Si](O[C@@H]1[C@@](CI)(CO)O[C@@H](N2C=C(C)C(=O)NC2=O)C1)(C(C)(C)C)(C)C>CC(=O)CCC(=O)C>[NH:22]1[CH:30]=[C:28]([CH3:29])[C:26](=[O:27])[NH:25][C:23]1=[O:24]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 18650253HCID 18650253, compoundHCID 18650254HCID 18650254, compound

Product 1

HCID 1135Thymine

Reagents, catalysts & solvents 1

HCID 80352,5-HexanedioneSolvent

Conditions

Temperature
130 °C

Procedure

A solution of the 4'-α and 4'-β isomers of 3'-O-t-butyldimethylsilyl-4'-methanesulfonyloxymethylthymidine (88 mg, 0.18 mM) prepared, e.g., as described in Preparation 5, with NaI (270 mg, 1.8 mM) in 2,5-hexanedione (3 ml) was stirred at 130° C. for 2 hours, at 95° C. for 60 hours and at 130° C. for 24 hours. Solid material was filtered off and the solvent was removed by evaporation under reduced pressure. The residue was purified (twice) by flash chromatography on silica gel. The column was eluted with CH2Cl2 +4% CH3OH+0.05% acetic acid followed by CH2Cl2 +4% CH3OH. The two fractions with identical TLCs and were combined yielding a mixture of the 4'-α and 4'-β isomers of 3'-O--t-butyldimethylsilyl-4'-iodomethylthymidine (70 mg, 0.14 mM), as a light brownish material. MS(CI) 514(M+NH4)+.

Workup

  1. filtrationSolid material was filtered off
  2. customthe solvent was removed by evaporation under reduced pressure
  3. customThe residue was purified (twice) by flash chromatography on silica gel
  4. washThe column was eluted with CH2Cl2 +4% CH3OH+0.05% acetic acid
  5. customThe two fractions with identical TLCs and were combined yielding

Sources & evidence

ORD record
ord-b5513f39940245ae887bc4bf8b59a5c3
Source dataset
uspto-grants-1993_03
Patent number
US05192749

Reaction notes

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