5-Fluorouracil → 1-[1-(2-Hydroxyethoxy)propyl]-5-fluorouracil

HRID 1649105Notes

Reaction equation

HRID 1649105 reaction equation
C[Si]([C:5]1[NH:10][C:9](=[O:11])[N:8]([Si](C)(C)C)[C:7](=[O:16])[C:6]=1[F:17])(C)C.FC1C(=O)NC(=O)NC=1.[CH2:27]([CH:29]1[O:33][CH2:32][CH2:31][O:30]1)[CH3:28].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.CO.C(O)CO>[OH:33][CH2:32][CH2:31][O:30][CH:29]([N:10]1[CH:5]=[C:6]([F:17])[C:7](=[O:16])[NH:8][C:9]1=[O:11])[CH2:27][CH3:28]

Participants

8

Reactant 4

HCID 33855-FluorouracilHCID 173812-Ethyl-1,3-dioxolaneHCID 516892Sodium BicarbonateHCID 68585259HCID 68585259, compound

Product 1

HCID 130571221-[1-(2-Hydroxyethoxy)propyl]-5-fluorouracil

Reagents, catalysts & solvents 3

HCID 174Ethylene GlycolSolventHCID 887MethanolSolventHCID 6212ChloroformSolvent2×

Procedure

Bis(trimethylsilyl)-5-fluorouracil which had been prepared by treating 5-fluorouracil (10 g) as in Example 1 was dissolved in chloroform (20 ml). Separately prepared 2-ethyl-1,3-dioxolan (15 ml) from propionyldehyde (25 ml) and ethylene glycol (25 ml) was added to the above solution. Then, to the mixture was added dropwise a solution of anhydrous stannic chloride (6 ml) in chloroform (15 ml) under cooling in an ice bath for one hour. Following stirring at room temperature for one hour, the reaction mixture was poured into methanol (100 ml) containing sodium bicarbonate (30 g) and, after removing the resulting precipitate by filtration, the filtrate was evaporated under reduced pressure. The residue was dissolved in water (10 ml), purified by column chromatography with use of Amberlite XAD-4 (Rohm and Haas Co.), and then treated with benzene to give 8.7 of crystalline 1-[1-(2-hydroxyethoxy)propyl]-5-fluorouracil.

Workup

  1. temperatureunder cooling in an ice bath for one hour
  2. customafter removing the resulting precipitate
  3. filtrationby filtration
  4. customthe filtrate was evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in water (10 ml)
  6. custompurified by column chromatography with use of Amberlite XAD-4 (Rohm and Haas Co.)
  7. additiontreated with benzene

Sources & evidence

ORD record
ord-ea2c0faa4d74479f85e45ecab32feb2e
Source dataset
uspto-grants-1983_11
Patent number
US04415573

Reaction notes

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