US3954758A
Expired / Lapsed
US
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Process for fluorinating uracil and derivatives thereof
Assignee: PCR-PUERTO RICO INCORPORATED A CORP OF
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Filing: 1971-10-04
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Granted: 1976-05-04
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Expires: 1991-10-04
Abstract
Abstract Direct fluorination of uracil and its derivatives, in the presence of an aqueous solvent, by fluorine gas to produce 5-fluorouracil and 5-fluorouracil derivatives is disclosed. Novel compounds produced by the reaction, such as 5,5-difluoro-6-hydroxy-5,6-dihydrouracil are also disclosed. The derivatives of 5-fluorouracil are useful as germicidal agents while 5-fluorouracil itself is a known cancer chemotherapy agent.
Inventors
- 👤 Paul D. Schuman
- 👤 Paul Tarrant
- 👤 Dale A. Warner
- 👤 Geraldine Westmoreland
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 22:42
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/46; C07D239/52; C07D239/54; C07D239/545; C07D239/553; C07D239/20; C07D239/22
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
32 words
Method of making 5-fluorouracil consisting essentially of reacting, in an aqueous medium and at a temperature between about 9°C. and about 100°C., uracil and gaseous fluorine, and dehydrating the resulting reaction product.
Claim 2
Dependent Claim
32 words
Method of making 5-fluorouracil consisting essentially of reacting, in an aqueous medium and at a temperature between about 9°C. and about 100°C., uracil and gaseous fluorine, and dehydrating the resulting reaction product.
Claim 3
Dependent Claim
13 words
Method of claim 1, wherein said temperature is about 50°C. to about 9°C.
Claim 4
Dependent Claim
16 words
Method of claim 1, wherein the molar ratio of fluorine to uracil is at least 1:1.
Claim 5
Dependent Claim
11 words
Method of claim 3, wherein said ratio is 1:1 to 2:1.
Claim 6
Dependent Claim
50 words
Method of claim 1, in which the uracil is about 0.01% by weight to about 90% by weight of the total of uracil and water, and the fluorine is diluted with an inert gas at a ratio by volume of inert gas to fluorine of about 9:1 to about 1:3.
Claim 7
Dependent Claim
27 words
Method of making 5-fluoro-6-hydroxy-5,6-dihydrouracil monohydrate consisting essentially of reacting gaseous fluorine with uracil at a temperature of about 9°C. to about 100°C. in the presence of water.
Claim 8
Dependent Claim
27 words
Method of making 5-fluoro-6-hydroxy-5,6-dihydrouracil monohydrate consisting essentially of reacting gaseous fluorine with uracil at a temperature of about 9°C. to about 100°C. in the presence of water.
Claim 9
Dependent Claim
40 words
Method of making 5-fluorouracil consisting essentially of reacting fluorine and uracil in an aqueous medium at a temperature of about 9°C. to about 100°C. to form a reaction product comprising 5-fluoro-6-hydroxy-5,6-dihydrouracil monohydrate, and dehydrating the 5-fluoro-6-hydroxy-5,6-dihydrouracil monohydrate to form 5-fluorouracil.
Claim 10
Dependent Claim
40 words
Method of making 5-fluorouracil consisting essentially of reacting fluorine and uracil in an aqueous medium at a temperature of about 9°C. to about 100°C. to form a reaction product comprising 5-fluoro-6-hydroxy-5,6-dihydrouracil monohydrate, and dehydrating the 5-fluoro-6-hydroxy-5,6-dihydrouracil monohydrate to form 5-fluorouracil.
Claim 11
Dependent Claim
21 words
Method of claim 7 in which the reaction product is dehydrated by heating in the presence of a strong inorganic acid.
Claim 12
Dependent Claim
20 words
Method of claim 7 in which the dehydration step is performed by refluxing an aqueous solution of said 5-fluoro-6-hydroxy-5,6-dihydrouracil monohydrate.
Claim 13
Dependent Claim
115 words
A process consisting essentially of reacting at a temperature of about 9 to 100°C. a uracil derivative of the formula: ##SPC12## with gaseous fluorine in the presence of water to prepare a compound of the general formula: ##SPC13## wherein R 1 is hydrogen, halogen, lower alkyl, or taken with R 3 is a 5,6 double bond; R 2 is hydrogen, hydroxyl or lower alkyl; R 3 is hydroxyl or taken with R 1 is a 5,6 double bond provided, however, that when both R 2 and R 3 are hydroxyl, then R 2 taken with R 3 is = O; R 4 is hydrogen or lower alkyl, and R 5 is hydrogen or lower alkyl.
Claim 14
Dependent Claim
115 words
A process consisting essentially of reacting at a temperature of about 9 to 100°C. a uracil derivative of the formula: ##SPC12## with gaseous fluorine in the presence of water to prepare a compound of the general formula: ##SPC13## wherein R 1 is hydrogen, halogen, lower alkyl, or taken with R 3 is a 5,6 double bond; R 2 is hydrogen, hydroxyl or lower alkyl; R 3 is hydroxyl or taken with R 1 is a 5,6 double bond provided, however, that when both R 2 and R 3 are hydroxyl, then R 2 taken with R 3 is = O; R 4 is hydrogen or lower alkyl, and R 5 is hydrogen or lower alkyl.
References Cited (Backward Citations)
US3277092A
Cited
US3682917A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-05-04 | 1979-11-03 | 1980-05-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-05-04 | 1983-11-03 | 1984-05-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-05-04 | 1987-11-03 | 1988-05-04 | $7700.00 | Window Closed / Lapsed |