Idoxuridine → HCID 67117307, compound

HRID 2364919Notes

Reaction equation

HRID 2364919 reaction equation
I[C:2]1[C:3](=[O:17])[NH:4][C:5](=[O:16])[N:6]([CH:15]=1)[C@@H:7]1[O:14][C@H:11]([CH2:12][OH:13])[C@@H:9]([OH:10])[CH2:8]1.C(N(CCCC)CCCC)CCC.[CH2:31]=[CH:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].C(Cl)(Cl)Cl>CN(C=O)C.O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CO>[CH3:37][CH2:36][CH2:35][CH2:34][CH:33]=[CH:32][CH3:31].[C@@H:7]1([N:6]2[CH:15]=[CH:2][C:3](=[O:17])[NH:4][C:5]2=[O:16])[O:14][C@H:11]([CH2:12][OH:13])[C@@H:9]([OH:10])[CH2:8]1

Participants

9

Reactant 4

HCID 5905IdoxuridineHCID 6212ChloroformHCID 7622TributylamineHCID 116101-Heptene

Product 1

HCID 67117307HCID 67117307, compoundYield 97%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

5-iodo-2′-deoxyuridine (1) (500 mg, 1.41 mmol) was dissolved in DMF (2.5 ml) and dioxane (2.5 ml), and palladium acetate (31 mg, 0.14 mmol) was added thereto to obtain a suspension. Tributylamine (340 μl, 1.41 mmol) and 1-heptene (5 ml, 3.53 mmol) were further added, and the reaction was carried out at 100° C. for 20 minutes by heating by microwaves. After confirming at least 90% decrease in the reaction materials by TLC (CHCl3:MeOH=9:1), the obtained sample was purified by using a silica gel column with a development solvent of CHCl3:MeOH=9:1. HU was found to be 445 mg, 1.36 mmol and the yield was 97%. The target compound was determined by 1H NMR for identification. In addition, mass analysis was carried out based on MALDI-TOF MS, and it was identified as the target compound (calcd. for C16H25N2O5 [M+H]+325.179, found 325.801).

Workup

  1. customto obtain a suspension
  2. temperatureby heating by microwaves
  3. customthe obtained sample was purified

Sources & evidence

ORD record
ord-dc2c871dcdba41d385dd097d271213f8
Source dataset
uspto-grants-2014_04
Patent number
US08697357B2

Reaction notes

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