Ammonia → 3'-Azido-2',3'-dideoxy-5-fluorouridine

HRID 1052093Notes

Reaction equation

HRID 1052093 reaction equation
[N:1]([C@@H:4]1[C@@H:8]([CH:9](C(=O)C2C=CC=CC=2)[OH:10])[O:7][C@@H:6]([N:19]2[CH:26]=[C:25]([F:27])[C:23](=[O:24])[NH:22][C:20]2=[O:21])[CH2:5]1)=[N+:2]=[N-:3].N>CO>[N:1]([C@@H:4]1[C@@H:8]([CH2:9][OH:10])[O:7][C@@H:6]([N:19]2[CH:26]=[C:25]([F:27])[C:23](=[O:24])[NH:22][C:20]2=[O:21])[CH2:5]1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 121363287HCID 121363287, compound

Product 1

HCID 4513683'-Azido-2',3'-dideoxy-5-fluorouridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3′-Azido-5′-benzoyl-2′,3′-dideoxy-5-fluorouridine prepared in step B above (2.5 g) was suspended in methanol saturated with ammonia (200 mL) and stirred using a magnetic stirrer at room temperature for 12 hours. Subsequently, the methanol was removed using a vacuum evaporator, and the solid residue was subjected to column chromatography on silica gel with chloroform-methanol (40:1, v/v) as the mobile phase. Yield of AddFU: 1.64 g, 91%.

Workup

  1. customat room temperature
  2. customfor 12 hours
  3. customSubsequently, the methanol was removed
  4. customa vacuum evaporator

Sources & evidence

ORD record
ord-73d6f124fe254c6e86445be08362d673
Source dataset
uspto-grants-2016_07
Patent number
US09388209B2

Reaction notes

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