5-Fluorouracil → 1-(1-Hydroxymethylpropyloxy)-methyl-5-fluorouracil
Reaction equation
[CH2:1]([CH:3]1[CH2:7][O:6]C[O:4]1)[CH3:2].[CH2:8](O)C(O)CC.C[Si]([C:18]1[NH:23][C:22](=[O:24])[N:21]([Si](C)(C)C)[C:20](=[O:29])[C:19]=1[F:30])(C)C.FC1C(=O)NC(=O)NC=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.CO>[OH:6][CH2:7][CH:3]([O:4][N:23]1[CH:18]=[C:19]([F:30])[C:20](=[O:29])[N:21]([CH3:8])[C:22]1=[O:24])[CH2:1][CH3:2]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
4-Ethyl-1,3-dioxolane (10 ml) prepared from butane-1,2-diol was added to bis(trimethylsilyl)-5-fluorouracil prepared from 5-fluorouracil (10 g) as in Example 1. To the mixture was added dropwise a solution of anhydrous stannic chloride (6 ml) in chloroform (15 ml) over one hour under cooling in an ice bath followed by 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, 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 treated with benzene to give 6.9 g of crystalline 1-(1-hydroxymethylpropyloxy)-methyl-5-fluorouracil.
Workup
- temperatureunder cooling in an ice bath
- customafter removing the resulting precipitate
- customthe filtrate was evaporated under reduced pressure
- dissolutionThe residue was dissolved in water (10 ml)
- custompurified by column chromatography with use of Amberlite XAD-4 (Rohm and Haas Co.)
- additiontreated with benzene
Sources & evidence
- ORD record
- ord-86475d75c42945d7b6a596c5f8ea7110
- Source dataset
- uspto-grants-1983_11
- Patent number
- US04415573
Reaction notes
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