Triethylsilane → 5-[3-(Trifluoroacetamido)propyl]cytidine

HRID 43235Notes

Reaction equation

HRID 43235 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]([NH:5][CH2:6][C:7]#[C:8][C:9]1[C:10]([NH2:25])=[N:11][C:12](=[O:24])[N:13]([CH:23]=1)[C@@H:14]1[O:22][C@H:19]([CH2:20][OH:21])[C@@H:17]([OH:18])[C@H:15]1[OH:16])=[O:4].C([SiH](CC)CC)C>CO.[OH-].[Pd+2].[OH-]>[F:26][C:2]([F:1])([F:27])[C:3]([NH:5][CH2:6][CH2:7][CH2:8][C:9]1[C:10]([NH2:25])=[N:11][C:12](=[O:24])[N:13]([CH:23]=1)[C@@H:14]1[O:22][C@H:19]([CH2:20][OH:21])[C@@H:17]([OH:18])[C@H:15]1[OH:16])=[O:4]

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 866586305-[3-(Trifluoroacetamido)propynyl]cytidine

Product 1

HCID 866586315-[3-(Trifluoroacetamido)propyl]cytidineYield 71%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

5-[3-(trifluoroacetamido)propynyl]cytidine (1.25 g, 3.19 mmol, 1.00 equiv.) was dissolved in methanol (30 mL). Palladium hydroxide (0.25 g, 20 wt./wt. % based on propynyl cytidine) and triethylsilane (3.71 g, 31.90 mmol, 10.00 equiv.) were added to the reaction mixture. After 20-24 hours at ambient temperature, the reaction mixture was filtered through glass fiber and the filtrate was concentrated under reduced pressure giving a dark brown residue. The residue was purified by flash chromatography. Removal of solvent from the appropriate fractions afforded 0.85 g (71%) of 5-[3-(trifluoroacetamido)propyl]cytidine as a cream colored solid, which was confirmed by 1H-NM.

Workup

  1. filtrationthe reaction mixture was filtered through glass fiber
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customgiving a dark brown residue
  4. customThe residue was purified by flash chromatography
  5. customRemoval of solvent from the appropriate fractions

Sources & evidence

ORD record
ord-bd68c8b221504e7eaf542c851bc9e8e3
Source dataset
uspto-grants-2013_09
Patent number
US08536323B2

Reaction notes

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