5-Fluorouracil → Tegafur

HRID 127694Notes

Reaction equation

HRID 127694 reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[O:10]1[CH:14]=[CH:13][CH2:12][CH2:11]1>N1C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[O:10]1[CH2:14][CH2:13][CH2:12][CH:11]1[N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[NH:4][C:5]1=[O:8]

Participants

5

Reactant 2

HCID 33855-FluorouracilHCID 709342,3-Dihydrofuran

Product 1

HCID 5386TegafurYield 69%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 1049PyridineSolvent3×

Conditions

Temperature
80 °C

Procedure

In 40 ml of pyridine were dissolved 5.2 g of 5-fluorouracil. The solution was ice cooled and 0.8 g of titanium tetrachloride was added thereto. Then, 6 ml of 2,3-dihydrofuran in 20 ml of pyridine were added to the mixture in 1.5 hours while stirring it at 80° C. The reaction was continued for 4 hours. After completion of the reaction, pyridine was removed from the reaction liquid by distillation and 500 ml of chloroform and 5 g of silica gel were added to the residue. The mixture was decolored and filtered and the filtrate was concentrated to obtain 5.5 g of 1-(2-tetrahydrofuryl)-5-fluorouracil in a yield of 69%.

Workup

  1. temperaturecooled
  2. customwas removed from the reaction liquid by distillation and 500 ml of chloroform and 5 g of silica gel
  3. additionwere added to the residue
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f67849dff878420f9ebbdb848aa04a0c
Source dataset
uspto-grants-1981_03
Patent number
US04256885

Reaction notes

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