Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 5-Fluorouracil | HCID 3385 | — |
| Reactant | Hydrazine | HCID 9321 | — |
| Reactant | Hydrazine hydrate (1:1) | HCID 24654 | — |
| Reactant | Phosphorus oxychloride | HCID 24813 | — |
| Reactant | 4,4,4-Trifluoro-1-phenyl-1,3-butanedione | HCID 67589 | — |
| Reactant | m-Chloroperbenzoic acid | HCID 70297 | — |
| Reactant | 5-Fluoropyrimidin-2-one | HCID 101498 | — |
| Reactant | 5-Fluoro-2-methylsulfonylpyrimidine | HCID 566379 | — |
| Reactant | 5-Fluoro-4-thiouracil | HCID 2781213 | — |
| Reactant | Sodium methanethiolate | HCID 4378561 | — |
| Reactant | HCID 12509326 | HCID 12509326 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 10177049 | HCID 10177049 | — |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06531492B1 |
|---|
| Source dataset | uspto-grants-2003_03 |
|---|
| ORD ID | ord-1d382a67255843e1abbfefb43019cb3c |
|---|
| Source note | uspto-grants-2003_03 |
|---|
