Triethylamine → 5-Et-ddU

HRID 2119040Notes

Reaction equation

HRID 2119040 reaction equation
[CH2:1]([C:3]1[C:4](=[O:18])[NH:5][C:6](=[O:17])[N:7]([CH:16]=1)[C@@H:8]1[O:14][C@H:11]([CH2:12][OH:13])[C@@H:10](I)[CH2:9]1)[CH3:2].C(N(CC)CC)C.[H][H]>CO.[Pd]>[CH2:1]([C:3]1[C:4](=[O:18])[NH:5][C:6](=[O:17])[N:7]([CH:16]=1)[C@@H:8]1[O:14][C@H:11]([CH2:12][OH:13])[CH2:10][CH2:9]1)[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 451824Uridine, 2',3'-dideoxy-5-ethyl-3'-iodo-HCID 178418361HCID 178418361, compound

Product 1

HCID 4514525-Et-ddUYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-Ethyl-3'-iodo-2',3'-dideoxyuridine (432 mg, 0.87 mmole) is dissolved in methanol (40 ml) and triethylamine (0.5 ml) is added along with 10% Pd/C (200 mg). The mixture is then stirred in an atmosphere of hydrogen at room temperature for 30 min. After filtration of catalyst, the filtrate is evaporated to dryness. Purification of the product was achieved on silica gel plates using chloroform-methanol (20:1) to obtain a solid (150 mg, 75%).

Workup

  1. filtrationAfter filtration of catalyst
  2. customthe filtrate is evaporated to dryness
  3. customPurification of the product

Sources & evidence

ORD record
ord-4848d14c350f46678b0fe26dcce9dab9
Source dataset
uspto-grants-1987_07
Patent number
US04681933

Reaction notes

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