5-Fluorouracil → HCID 10177049, compound

HRID 1860591Notes

Reaction equation

F[C:2]1[C:3](=S)[NH:4][C:5](=O)[NH:6][CH:7]=1.F[C:11]1[C:12](=O)[NH:13]C(=O)[NH:15][CH:16]=1.FC1C=NC(=O)NC=1.C[S:28]([C:31]1N=CC(F)=CN=1)(=[O:30])=[O:29].P(Cl)(Cl)(Cl)=O.C[S-].[Na+].Cl[C:47]1[CH:52]=[CH:51][CH:50]=[C:49](C(OO)=O)[CH:48]=1.NN.O.NN.CS(C1N=CC(NN)=CN=1)(=O)=O.[F:74][C:75]([F:88])([F:87])C(=O)CC(C1C=CC=CC=1)=O>C(O)C>[CH3:31][S:28]([C:5]1[N:4]=[CH:3][C:2]([N:13]2[C:12]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)=[CH:11][C:16]([C:75]([F:88])([F:87])[F:74])=[N:15]2)=[CH:7][N:6]=1)(=[O:29])=[O:30]

Participants

Procedure

5-Fluoro-4-thiouracil can be prepared from 5-fluorouracil as described (J. Med. Chem., Vol. 6, pp. 697-701 (1963)). 5-Fluoro-2(1H)-pyrimidinone can be subsequently prepared as described (Acta Chem. Scand., Vol. 23, pp. 294-299 (1969)). 5-Fluoro-2(1H)-pyrimidinone can then be converted to 2-methanesulfonyl-5-fluoropyrimidine by treatment with phosphorus oxychloride, followed by reaction with sodium methanethiolate and oxidation with m-chloroperbenzoic acid as described (Acta Chem. Scand., Vol. B39, pp. 696-696 (1985)). Conversion to the hydrazine is then effected by treatment of 2-methylsulfonyl-5-fluoropyrimidine with hydrazine hydrate in ethanol (Coll. Czech. Chem. Commun., Vol. 37, pp. 1721-17330 (1972)). Subsequent reaction of 2-methylsulfonyl-5-hydrazinopyrimidine with 4,4,4-trifluoro-1-phenyl-1,3-butanedione will then produce the title compound.

Sources & evidence

ORD record: ord-1d382a67255843e1abbfefb43019cb3c
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06531492B1

Reaction notes

Loading…

Reaction equation

Participants

Reactant 11

Product 1

Reagents, catalysts & solvents 1

Procedure

Sources & evidence

Reaction notes