5-Fluorouracil → 1-Methanesulfonyl-5-fluorouracil

HRID 918393Notes

Reaction equation

[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>CO>[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[N:6]([S:23]([CH3:22])(=[O:25])=[O:24])[CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2.6 g. (0.02 mole) of 5-fluorouracil and 1.52 g (0.011 mole) of anhydrous potassium carbonate were suspended in 50 ml. of dioxane and then 2.53 g (0.022 mole) of methanesulfonyl chloride in 20 ml. of dioxane was dropwise added thereto. After stirring at 80°C. for 10 hours, the reaction mixture was filtered. The filtrate was concentrated under reduced pressure and a resinous residue was obtained. The residue was dissolved in a small amount of methanol and allowed to stand at 0°C. overnight. There was obtained 1.48 g (45.4% yield) of 5-fluoro-1 -methanesulfonyluracil. Recrystallization of the product from methanol gave leaflets melting at 223°-224°C. The results of an elementary analysis thereof were well in agreement with the calculated value as follows:

Workup

filtrationthe reaction mixture was filtered
concentrationThe filtrate was concentrated under reduced pressure
customa resinous residue was obtained
waitto stand at 0°C. overnight

Sources & evidence

ORD record: ord-d30c5a64fb5c4515a760cc4923b5b9c1
Source dataset: uspto-grants-1976_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03971784

Reaction notes

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