5-Fluorouracil → Tegafur

HRID 127691Notes

Reaction equation

HRID 127691 reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.Cl.N1C=CC=CC=1.[O:17]1[CH:21]=[CH:20][CH2:19][CH2:18]1>N1C=CC=CC=1>[O:17]1[CH2:21][CH2:20][CH2:19][CH:18]1[N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[NH:4][C:5]1=[O:8]

Participants

5

Reactant 3

HCID 33855-Fluorouracil2×HCID 709342,3-DihydrofuranHCID 10176127Pyridinium chloride

Product 1

HCID 5386Tegafur

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 50 ml of pyridine were dissolved 2.5 g of 5-fluorouracil and 2.4 g of pyridine hydrochloride. To this solution were added 4.5 ml of 2,3-dihydrofuran in 4 portions and the mixture was reacted for 20 hours at 120° C. in an oil bath. After the reaction, a small amount of the reaction liquid was extracted and subjected to thin layer chromatography to check the state of preceeding of the reaction whereby the composition of the product was 90% of the end product, 5% of unreacted 5-fluorouracil and 5% of by-products. The reaction liquid was treated in the same manner as described in Example 7 to obtain 2.6 g of 1-(2-tetrahydrofuryl)-5-fluorouracil. The yield of the end product was 70% based on the initially used 5-fluorouracil.

Workup

  1. customthe mixture was reacted for 20 hours at 120° C. in an oil bath
  2. customAfter the reaction
  3. customa small amount of the reaction liquid
  4. extractionwas extracted
  5. customthe state of preceeding of the reaction whereby the composition of the product
  6. customThe reaction liquid
  7. additionwas treated in the same manner

Sources & evidence

ORD record
ord-a1c3d981bba74e7682d2d347f78c65d7
Source dataset
uspto-grants-1981_03
Patent number
US04256885

Reaction notes

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