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

HRID 371915Notes

Reaction equation

HRID 371915 reaction equation
FC1C(=O)NC(=O)NC=1.[C:10](Br)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:19]([N:27]1[C:32](=[O:33])[C:31]([F:34])=[CH:30][NH:29][C:28]1=[O:35])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>N1C=CC=CC=1>[C:10]([N:29]1[CH:30]=[C:31]([F:34])[C:32](=[O:33])[N:27]([C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:28]1=[O:35])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 33855-FluorouracilHCID 12056Benzoyl bromideHCID 126908273-Benzoyl-5-fluoropyrimidine-2,4(1H,3H)-dione

Product 1

HCID 126908291,3-Dibenzoyl-5-fluoropyrimidine-2,4(1H,3H)-dioneYield 11.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In the same manner as described in Example 1 but using 2.6 g (0.02 mole) of 5-fluorouracil, 10 ml of absolute pyridine and 7.4 g (0.04 mole) of benzoyl bromide, 1.6 g of 3-N-benzoyl-5-fluorouracil (yield, 34%) and 270 mg of 1,3-di-N-benzoyl-5-fluorouracil (yield, 4%) were obtained.

Sources & evidence

ORD record
ord-e92f15ba59e240bd973280dbbd8f4cdf
Source dataset
uspto-grants-1978_05
Patent number
US04088646

Reaction notes

Loading…