Triethylamine → Doxifluridine

HRID 1759379Notes

Reaction equation

HRID 1759379 reaction equation
C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([CH3:14])[O:7][C@H:6]1[N:15]1[CH:22]=[C:21]([F:23])[C:19](=[O:20])[NH:18][C:16]1=[O:17])(=O)C.C(N(CC)CC)C>CO>[F:23][C:21]1[C:19](=[O:20])[NH:18][C:16](=[O:17])[N:15]([CH:22]=1)[C@@H:6]1[O:7][C@H:8]([CH3:14])[C@@H:9]([OH:10])[C@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 149189135'-Deoxy-5-fluorouridine 2',3'-diacetate

Product 1

HCID 18343DoxifluridineYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.5 g of 1-(5-deoxy-2,3-di-O-acetyl-β-D-ribofuranosyl)-5-fluorouracil were heated under reflux in 60 ml of methanol in the presence of 0.3 ml of triethylamine until starting material could no longer be detected by thin-layer chromatography. The colourless, clear solution was concentrated under reduced pressure and the white, crystalline material obtained was recrystallised from water. There was obtained pure 5'-deoxy-5-fluorouridine, m.p. 192°-193° C., in 98% yield.

Workup

  1. concentrationThe colourless, clear solution was concentrated under reduced pressure
  2. customthe white, crystalline material obtained
  3. customwas recrystallised from water

Sources & evidence

ORD record
ord-1646790c81194bc08b6e7ff20bdda002
Source dataset
uspto-grants-1982_07
Patent number
US04340729

Reaction notes

Loading…