HCID 6481573, compound → Thymidine

HRID 333486Notes

Reaction equation

HRID 333486 reaction equation
C(O[CH2:9][C:10]1[C:11](=[O:25])[NH:12][C:13](=[O:24])[N:14]([CH:23]=1)[C@@H:15]1[O:22][C@H:19]([CH2:20][OH:21])[C@@H:17]([OH:18])[CH2:16]1)C1C=CC=CC=1>C(O)C.[Pd]>[C@@H:15]1([N:14]2[CH:23]=[C:10]([CH3:9])[C:11](=[O:25])[NH:12][C:13]2=[O:24])[O:22][C@H:19]([CH2:20][OH:21])[C@@H:17]([OH:18])[CH2:16]1

Participants

4

Reactant 1

HCID 6481573HCID 6481573, compound

Product 1

HCID 5789ThymidineYield 90.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5-(benzyloxy)methyl-2′-deoxyuridine (29 mg, 0.082 mmol) in absolute ethanol (2 mL) under a nitrogen atmosphere was added 10 mg of palladium on activated carbon (10 wt. %, 10 mg) (CAUTION: flammable solid! Ensure handling in oxygen-free atmosphere). The mixture was flushed with hydrogen gas and stirred at room temperature for 30 minutes while being monitored by TLC every five minutes. The mixture was filtered, concentrated under reduced pressure, and dried under vacuum to yield thymidine (18 mg, 88%) that was identified by comparison to the authentic sample (TLC and 1H NMR).

Workup

  1. customThe mixture was flushed with hydrogen gas
  2. waitwhile being monitored by TLC every five minutes
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated under reduced pressure
  5. customdried under vacuum

Sources & evidence

ORD record
ord-076ce4170763437aa09af164fd05b353
Source dataset
uspto-grants-2014_11
Patent number
US08877905B2

Reaction notes

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