HCID 6481573, compound → Thymidine

HRID 1499663Notes

Reaction equation

HRID 1499663 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>[Pd].C(O)C>[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 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

Chemical Cleavage Using Heterogenous Palladium Catalyst: 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-2abe78931e41404ea6cfd41c502dacf7
Source dataset
uspto-grants-2015_12
Patent number
US09200319B2

Reaction notes

Loading…