5-Fluorouracil → Butanoic acid, (5-fluoro-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)methyl ester
Reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.C(N(CC)CC)C.[C:17]([O:22][CH2:23]Cl)(=[O:21])[CH2:18][CH2:19][CH3:20]>CN(C)C=O>[C:17]([O:22][CH2:23][N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[NH:4][C:5]1=[O:8])(=[O:21])[CH2:18][CH2:19][CH3:20]Participants
Procedure
In a 300 cc 4-necked flask equipped with a stirrer, a thermometer and a dropping funnel were placed 80 ml of dimethylformamide. Then, 10.41 g (0.08 mol) of 5-fluorouracil was dissolved in the dimethylformamide and 24.29 g (0.24 mol) of triethylamine was added to this solution. To the mixture was added dropwise over 15 minutes 10.93 g (0.08 mol) of butyryloxymethyl chloride. The mixture was reacted together for 5 hours at room temperature and the reaction liquid was filtered to remove the precipitated triethylamine hydrochloride. The solvent was then distilled from the filtrate and the residue was subjected to a treatment using a column packed with silica gel and a mixture (1:1 in mixing ratio) of benzene and ethyl acetate whereby crude 1-butyryloxymethyl-5-fluorouracil was isolated. This crude product was recrystallized from benzene whereby 16.0 g of pure white crystals having a melting point of 96°~98° C. were obtained in a yield of 86.9%.
Workup
- customIn a 300 cc 4-necked flask equipped with a stirrer
- additionwas added to this solution
- customThe mixture was reacted together for 5 hours at room temperature
- customthe reaction liquid
- filtrationwas filtered
- customto remove the precipitated triethylamine hydrochloride
- distillationThe solvent was then distilled from the filtrate
Sources & evidence
- ORD record
- ord-d987e3e2181644b4b4850d65e0effd9c
- Source dataset
- uspto-grants-1981_05
- Patent number
- US04267326
Reaction notes
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