HCID 53771011, compound → HCID 54161311, compound

HRID 1602973Notes

Reaction equation

HRID 1602973 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH2:14][C:15]2[C:16](=[S:52])[NH:17][C:18](=[O:51])[N:19]([CH:50]=2)[C@@H:20]2[O:49][C@H:39]([CH2:40][O:41][Si](C(C)(C)C)(C)C)[C@@H:30]([O:31][Si](C(C)(C)C)(C)C)[C@H:21]2[O:22][Si](C(C)(C)C)(C)C)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(#N)C>[O:1]([C:8]1[CH:9]=[C:10]([CH2:14][C:15]2[C:16](=[S:52])[NH:17][C:18](=[O:51])[N:19]([CH:50]=2)[C@@H:20]2[O:49][C@H:39]([CH2:40][OH:41])[C@@H:30]([OH:31])[C@H:21]2[OH:22])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 53771011HCID 53771011, compound

Product 1

HCID 54161311HCID 54161311, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The product of step (iii) (3.5 g) was dissolved in acetonitrile (70 ml) and treated with a 1:1 hydrofluoric acid-pyridine complex (20 ml). After 3 hours the mixture was quenched with saturated aqueous sodium carbonate solution (100 ml) and the product extracted into ethyl acetate. The organic phase was collected, dried over magnesium sulphate and the solvent was removed under reduced pressure. The residue was purified by flash silica-gel chromatography eluting with chloroform-methanol mixtures to afford 5-((3-phenoxy)phenylmethyl)-4-thiouridine as a yellow powder (1.5 g).

Workup

  1. additiontreated with a 1:1 hydrofluoric acid-pyridine complex (20 ml)
  2. customAfter 3 hours the mixture was quenched with saturated aqueous sodium carbonate solution (100 ml)
  3. extractionthe product extracted into ethyl acetate
  4. customThe organic phase was collected
  5. dry with materialdried over magnesium sulphate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by flash silica-gel chromatography
  8. washeluting with chloroform-methanol mixtures

Sources & evidence

ORD record
ord-0651eb285c8445c5a496837a4f20ce0f
Source dataset
uspto-grants-1999_11
Patent number
US05985849

Reaction notes

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