5-Fluorouracil → 1-Benzoyl-5-fluoropyrimidine-2,4(1H,3H)-dione

HRID 918392Notes

Reaction equation

HRID 918392 reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.O1CCOCC1.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>N1C=CC=CC=1>[C:16]([N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[NH:4][C:5]1=[O:8])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 33855-FluorouracilHCID 7412Benzoyl chlorideHCID 312751,4-Dioxane

Product 1

HCID 134432881-Benzoyl-5-fluoropyrimidine-2,4(1H,3H)-dioneYield 42.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.6 g (0.02 mole) of 5-fluorouracil was suspended in a mixed solution of 35 ml. of dioxane and 10 ml. of pyridine and reacted with 6.7 g (0.048 mole) of benzoylchloride. The reaction mixture was treated in the same manner as in Example 1 and 2.00 g (42.5% yield) of 1-benzoyl-5-fluorouracil was obtained. The product was recrystallized from ethanol to give white needles melting at 170°-172°C. The results of an elementary analysis thereof were well in agreement with the calculated value as follows:

Workup

  1. additionThe reaction mixture was treated in the same manner as in Example 1

Sources & evidence

ORD record
ord-8da4430a6e7e4f2ea0622687cedc6f32
Source dataset
uspto-grants-1976_07
Patent number
US03971784

Reaction notes

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