Triethylamine → 5-Et-ddU

HRID 1905001Notes

Reaction equation

HRID 1905001 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-991fd344f4d4424fb25bac519567c26f
Source dataset
uspto-grants-1989_06
Patent number
US04841039

Reaction notes

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