US4024143A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Silylation of 5-fluoro-6-hydroxy or alkoxy pyrimidine
Assignee: PCR Group Inc
•
Filing: 1976-03-11
•
Granted: 1977-05-17
•
Expires: 1996-03-11
Abstract
Abstract A process for producing bis-silyl derivatives of fluorinated pyrimidines is disclosed, wherein a 5-fluoro-6-hydroxy or alkoxy pyrimidine is reacted with a silane, such as triethylchlorosilane. The intermediate product produced by that reaction, which is obtained in high yield, may then be reacted with a further compound, which can be a blocked sugar halide or 2-chlorotetrahydrofuran, to produce a nucleoside of the pyrimidine. The nucleosides are useful as antibacterial and antiviral agents, and in the treatment of cancer.
Inventors
- 👤 Paul D. Schuman
- 👤 Roy Anderson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 05:23
CPC Classifications
C; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
103 words
A process for producing bis-silyl derivatives of fluorinated pyrimidines, said process comprising reacting a 5-fluoropyrimidine of the formula ##STR4## or the monohydrate thereof, wherein R is hydrogen or lower alkyl, including lower fluoroalkyl, with at least a stoichiometric amount of silylating agent which is a. silane of the formula (R').sub.3 SiX wherein each R' is lower alkyl and X is halogen, and/or b. disilazane of the formula [(R').sub.3 Si].sub.2 NH wherein R' is lower alkyl, at a temperature of about room temperature to the boiling point of the reaction mixture, to produce a product of the formula ##STR5## wherein R' is defined above.
Claim 2
Dependent Claim
103 words
A process for producing bis-silyl derivatives of fluorinated pyrimidines, said process comprising reacting a 5-fluoropyrimidine of the formula ##STR4## or the monohydrate thereof, wherein R is hydrogen or lower alkyl, including lower fluoroalkyl, with at least a stoichiometric amount of silylating agent which is a. silane of the formula (R').sub.3 SiX wherein each R' is lower alkyl and X is halogen, and/or b. disilazane of the formula [(R').sub.3 Si].sub.2 NH wherein R' is lower alkyl, at a temperature of about room temperature to the boiling point of the reaction mixture, to produce a product of the formula ##STR5## wherein R' is defined above.
Claim 3
Dependent Claim
8 words
Process of claim 1, wherein X is chlorine
Claim 4
Dependent Claim
8 words
Process of claim 1, wherein R is hydrogen.
Claim 5
Dependent Claim
9 words
Process of claim 1, wherein R is lower alkyl.
Claim 6
Dependent Claim
26 words
Process of claim 1, wherein said silylating agent is a mixture of said silane and at least about 35 to about 50 mol % of disilazane.
Claim 7
Dependent Claim
11 words
Process of claim 5, wherein said fluoropyrimidine contains water of hydration.
Claim 8
Dependent Claim
9 words
Process of claim 1, wherein said disilazane is hexamethyldisilazane.
Claim 9
Dependent Claim
12 words
Process of claim 1, wherein said reaction is conducted under reflux conditions.
Claim 10
Dependent Claim
9 words
Process of claim 1, wherein the product is bis-trimethylsilyl-5-fluorouracil.
Claim 11
Dependent Claim
9 words
Process of claim 1, wherein the product is bis-triethylsilyl-5-fluorouracil.
Claim 12
Dependent Claim
37 words
Process of claim 1, wherein the starting pyrimidine compound is an anhydrous compound, and at least 3 mol equivalents of silylating agent are used, wherein at least one mole equivalent of the silylating agent is said silane.
Claim 13
Dependent Claim
34 words
Process of claim 1, wherein the starting pyrimidine compound is a monohydrate, and at least 4 mol equivalents of the silylating agent are used, wherein at least 2 mols of said silane are used.
Claim 14
Dependent Claim
42 words
Process of claim 1, wherein at least part of said silylating agent is said silane, and the amount of said silane is at least a stoichiometric amount, based on the --OH, RO--groups and the water of hydration present in said pyrimidine compound.
References Cited (Backward Citations)
US3354160A
Cited
US3635946A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-05-16 | 1980-11-15 | 1981-05-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-05-16 | 1984-11-15 | 1985-05-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-05-16 | 1988-11-15 | 1989-05-17 | $7700.00 | Window Closed / Lapsed |