US3954759A
Expired / Lapsed
US
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Process for preparation of 6-substituted 5-fluorouracil derivatives
Assignee: PCR Group Inc
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Filing: 1972-07-13
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Granted: 1976-05-04
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Expires: 1992-07-13
Abstract
Abstract The reaction of certain fluorinated pyrimidine derivatives with hydrogen donor compounds to produce 6-substituted 5-fluoropyrimidines is disclosed. The products so produced are useful in germicidal and antineoplastic applications, and can be converted into 5-fluorouracil, which has known utility in cancer chemotherapy.
Inventors
- 👤 Roy Anderson
- 👤 Paul D. Schuman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 16:44
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: 13
Claim 1
Independent Claim
164 words
A process for the preparation of 5-fluoro-6-substituted pyrimidine derivatives consisting essentially of reacting at least one pyrimidine derivative of the formula ##SPC13## wherein A is --OH or --NH 2 , R 1 is hydrogen, fluorine, chlorine, bromine or lower alkyl and R 2 is hydrogen or lower alkyl, and T is fluorine or lower acyloxy, wherein one or more hydrogen atoms may be substituted by halogen atoms, at a temperature of about -10 to about 72°C., with a compound having the formula T"H wherein T" is --OH, --OC(R') 3 , --SR, --OOCR', --NRR' or mixtures thereof wherein R is selected from the group consisting of lower alkyl and lower cycloalkyl, wherein one or more hydrogen atoms of the alkyl, or cycloalkyl may be replaced by fluorine, chlorine, or bromine atoms, and each R' is independently R or hydrogen, and wherein T" differs from T, to produce a pyrimidine compound of the formula: ##SPC14## wherein A, T", R 1 and R 2 are defined hereinabove.
Claim 2
Dependent Claim
164 words
A process for the preparation of 5-fluoro-6-substituted pyrimidine derivatives consisting essentially of reacting at least one pyrimidine derivative of the formula ##SPC13## wherein A is --OH or --NH 2 , R 1 is hydrogen, fluorine, chlorine, bromine or lower alkyl and R 2 is hydrogen or lower alkyl, and T is fluorine or lower acyloxy, wherein one or more hydrogen atoms may be substituted by halogen atoms, at a temperature of about -10 to about 72°C., with a compound having the formula T"H wherein T" is --OH, --OC(R') 3 , --SR, --OOCR', --NRR' or mixtures thereof wherein R is selected from the group consisting of lower alkyl and lower cycloalkyl, wherein one or more hydrogen atoms of the alkyl, or cycloalkyl may be replaced by fluorine, chlorine, or bromine atoms, and each R' is independently R or hydrogen, and wherein T" differs from T, to produce a pyrimidine compound of the formula: ##SPC14## wherein A, T", R 1 and R 2 are defined hereinabove.
Claim 3
Dependent Claim
10 words
Process according to claim 1, wherein T is lower haloacyloxy.
Claim 4
Dependent Claim
10 words
Process according to claim 2, wherein T is lower fluoroacyloxy.
Claim 5
Dependent Claim
9 words
Process according to claim 1 wherein T is fluorine.
Claim 6
Dependent Claim
12 words
Process according to claim 1, wherein said temperature is 20° to 60°C.
Claim 7
Dependent Claim
12 words
Process according to claim 5 wherein said temperature is about room temperature.
Claim 8
Dependent Claim
24 words
Process according to claim 1 wherein the molar ratio of said compound of formula T"H to said pyrimidine derivative is no greater than 100:1.
Claim 9
Dependent Claim
13 words
Process according to claim 7, wherein said molar ratio is 1.01:1 to 10:1.
Claim 10
Dependent Claim
18 words
Process according to claim 1, wherein said pyrimidine derivative, prior to said reaction, is in dry solid form.
Claim 11
Dependent Claim
11 words
Process according to claim 1, wherein T" is --OC(R') 3 .
Claim 12
Dependent Claim
18 words
Process according to claim 10, wherein A is --OH and R 1 and R 2 are both hydrogen.
Claim 13
Dependent Claim
16 words
Process according to claim 1, wherein said pyrimidine derivative is a mixture of 5-fluoro-6-trifluoroacetoxy-5,6-dihydrouracil and 5,6-difluoro-5,6-dihydrouracil.
References Cited (Backward Citations)
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 |