Sodium Iodide → HCID 10043561, compound

HRID 1489359Notes

Reaction equation

HRID 1489359 reaction equation
S(O[CH2:12][C@H:13]1[O:17][C@@H:16]([N:18]2[CH:26]=[C:24]([CH3:25])[C:22](=[O:23])[NH:21][C:19]2=[O:20])[CH2:15][C@@H:14]1[OH:27])(C1C=CC(C)=CC=1)(=O)=O.[I-:28].[Na+]>CC(C)=O>[I:28][CH2:12][C@H:13]1[O:17][C@@H:16]([N:18]2[CH:26]=[C:24]([CH3:25])[C:22](=[O:23])[NH:21][C:19]2=[O:20])[CH2:15][C@@H:14]1[OH:27]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 7302460((2R,3S,5R)-3-Hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 10043561HCID 10043561, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of the thymidine tosylate (10.65 g, 26.9 mmol) prepared according to the method of Example 23 in dry acetone (75 ml) was added sodium iodide (10 g, 66.7 mmol) and the mixture refluxed for 16 hours. The solvent was evaporated and diluted with ethyl acetate. The organic phase was washed with water (2×20 ml) and brine (10 ml) and dried with sodium sulfate. The title compound was crystallized from methanol as a white crystalline solid in 90-95% yield.

Workup

  1. temperaturethe mixture refluxed for 16 hours
  2. customThe solvent was evaporated
  3. additiondiluted with ethyl acetate
  4. washThe organic phase was washed with water (2×20 ml) and brine (10 ml)
  5. dry with materialdried with sodium sulfate
  6. customThe title compound was crystallized from methanol as a white crystalline solid in 90-95% yield

Sources & evidence

ORD record
ord-fe75f61d1e0d43f5a230a5f391aa57ae
Source dataset
uspto-grants-1997_10
Patent number
US05677439

Reaction notes

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