GB763041A - New pyrimidine derivatives - Google Patents
New pyrimidine derivativesInfo
- Publication number
- GB763041A GB763041A GB978252A GB978252A GB763041A GB 763041 A GB763041 A GB 763041A GB 978252 A GB978252 A GB 978252A GB 978252 A GB978252 A GB 978252A GB 763041 A GB763041 A GB 763041A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethylamino
- chloro
- chlorobenzeneazo
- chloropyrimidine
- methylamino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title abstract 2
- 150000003230 pyrimidines Chemical class 0.000 title abstract 2
- -1 alkyl radical Chemical class 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 238000010438 heat treatment Methods 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- PWJNRLSPEYCEMV-UHFFFAOYSA-N 4,6-dichloro-n,n-dimethylpyrimidin-2-amine Chemical compound CN(C)C1=NC(Cl)=CC(Cl)=N1 PWJNRLSPEYCEMV-UHFFFAOYSA-N 0.000 abstract 3
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 abstract 3
- 230000001476 alcoholic effect Effects 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- GIKMWFAAEIACRF-UHFFFAOYSA-N 2,4,5-trichloropyrimidine Chemical compound ClC1=NC=C(Cl)C(Cl)=N1 GIKMWFAAEIACRF-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- WOCATSRKZVWDLR-UHFFFAOYSA-N (1-aminopropan-2-ylideneamino)urea Chemical compound NCC(C)=NNC(N)=O WOCATSRKZVWDLR-UHFFFAOYSA-N 0.000 abstract 1
- VIEXAFPVDSRNAY-UHFFFAOYSA-N 1,2-dimethylguanidine;sulfuric acid Chemical compound OS(O)(=O)=O.CNC(N)=NC VIEXAFPVDSRNAY-UHFFFAOYSA-N 0.000 abstract 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 abstract 1
- ISZVFAGBGUCFPT-UHFFFAOYSA-N 2-(dimethylamino)-4-hydroxy-1h-pyrimidin-6-one Chemical compound CN(C)C1=NC(O)=CC(=O)N1 ISZVFAGBGUCFPT-UHFFFAOYSA-N 0.000 abstract 1
- XLUAFPZNWIHJGI-UHFFFAOYSA-N 2-[(2,6-dichloropyrimidin-4-yl)amino]-1,2-diphenylethanone Chemical compound ClC1=NC(=CC(=N1)Cl)NC(C(C1=CC=CC=C1)=O)C1=CC=CC=C1 XLUAFPZNWIHJGI-UHFFFAOYSA-N 0.000 abstract 1
- IBANAENPOYGIQH-UHFFFAOYSA-N 2-[[6-chloro-2-(dimethylamino)pyrimidin-4-yl]amino]-1,2-diphenylethanone Chemical compound ClC1=NC(=NC(=C1)NC(C(C1=CC=CC=C1)=O)C1=CC=CC=C1)N(C)C IBANAENPOYGIQH-UHFFFAOYSA-N 0.000 abstract 1
- LKPGGRAYFGWREN-UHFFFAOYSA-N 2-amino-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(N)C(=O)C1=CC=CC=C1 LKPGGRAYFGWREN-UHFFFAOYSA-N 0.000 abstract 1
- JPMVSOQQUQLZJU-UHFFFAOYSA-N 4-chloro-6-methoxy-n,n-dimethylpyrimidin-2-amine Chemical compound COC1=CC(Cl)=NC(N(C)C)=N1 JPMVSOQQUQLZJU-UHFFFAOYSA-N 0.000 abstract 1
- XFUSOCHHDLYPEX-UHFFFAOYSA-N 6-chloro-2-(dimethylamino)-1h-pyrimidin-4-one Chemical compound CN(C)C1=NC(O)=CC(Cl)=N1 XFUSOCHHDLYPEX-UHFFFAOYSA-N 0.000 abstract 1
- AXNSLRXEYVFBJS-UHFFFAOYSA-N 6-chloro-2-N,2-N,4-N-trimethylpyrimidine-2,4-diamine Chemical compound CN(C1=NC(=CC(=N1)NC)Cl)C AXNSLRXEYVFBJS-UHFFFAOYSA-N 0.000 abstract 1
- WOYUZQVWDISJCF-UHFFFAOYSA-N 6-chloro-2-n,2-n,4-n,4-n-tetramethylpyrimidine-2,4-diamine Chemical compound CN(C)C1=CC(Cl)=NC(N(C)C)=N1 WOYUZQVWDISJCF-UHFFFAOYSA-N 0.000 abstract 1
- NMWKOBZHKWXQFS-UHFFFAOYSA-N 6-chloro-2-n,2-n-dimethylpyrimidine-2,4-diamine Chemical compound CN(C)C1=NC(N)=CC(Cl)=N1 NMWKOBZHKWXQFS-UHFFFAOYSA-N 0.000 abstract 1
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract 1
- JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 150000005840 aryl radicals Chemical group 0.000 abstract 1
- NLOUUOHFCQJOCA-UHFFFAOYSA-N bis(2-benzyl-4-chlorophenyl)methanone Chemical compound C=1C=CC=CC=1CC1=CC(Cl)=CC=C1C(=O)C1=CC=C(Cl)C=C1CC1=CC=CC=C1 NLOUUOHFCQJOCA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003610 charcoal Substances 0.000 abstract 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract 1
- WAWUFPZLQFRIKX-UHFFFAOYSA-N ethyl 2-[[6-chloro-2-(dimethylamino)pyrimidin-4-yl]amino]acetate Chemical compound ClC1=NC(=NC(=C1)NCC(=O)OCC)N(C)C WAWUFPZLQFRIKX-UHFFFAOYSA-N 0.000 abstract 1
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/50—Three nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/20—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a pyrimidine ring
- C09B62/24—Azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention comprises pyrimidine derivatives of the general formula <FORM:0763041/IV(b)/1> in which Ar is an aryl radical which may optionally bear substituents, X is hydrogen or a lower alkyl radical, Y is a lower alkyl radical or X and Y together with the adjacent nitrogen atom form a heterocyclic ring, and Z is hydroxyl, amino, the group NX1Y1 (wherein X1 is hydrogen or a lower alkyl radical and Y1 is a lower alkyl radical), or the group NH-CRR11-COR1 (wherein R is hydrogen and R11 is hydrogen, phenyl or halophenyl radical and wherein R1 is phenyl or lower alkyl or alkoxy radical), provided that of the groups NXY and Z at least one is the residue of a secondary amine. The terms "lower alkyl" and "alkoxy" include up to 6 and 4 carbon atoms respectively. They are prepared by reacting a compound of the formula <FORM:0763041/IV(b)/2> with an aryldiazonium salt. The following examples are given: (1) dimethylguanidine sulphate is heated with sodium methoxide and then with diethyl malonate to give 2-dimethylamino-4,6-dihydroxypyrimidine, which is treated with phosphorus oxychloride to give 2-dimethylamino - 4,6 - dichloropyrimidine which, by heating with alcoholic ammonia is converted to 2-dimethylamino - 4 - amino - 6 - chloropyrimidine; the latter compound is then coupled with diazotized p-chloroaniline to yield 2-dimethyl-amino - 4 - amino - 5 - p - chlorobenzeneazo - 6-chloropyrimidine. (2) 2-Dimethylamino-4-methylamino - 6 - chloropyrimidine obtained by heating 2 - dimethylamino - 4,6 - dichloropyrimidine with alcoholic methylamine is coupled with diazotized p-chloroaniline to yield 2 - dimethylamino - 4 - methylamino - 5 - p-chlorobenzeneazo - 6 - chloropyrimidine. (3) By a similar process there are obtained 2,4-bis (dimethylamino) - 6 - chloropyrimidine and 2,4-bis(dimethylamino) - 5 - p - chlorobenzeneazo-6-chloropyrimidine. (4) Desylamine is reacted with trichloropyrimidine to give 2,4 - dichloro-6-desylaminopyrimidine which is heated with alcoholic dimethylamine to give 4-chloro-6-desylamino - 2 - dimethylaminopyrimidine and coupled with diazotized p-chloroaniline to yield 4 - chloro - p - chlorobenzeneazo - 6 - desylamino - 2 - dimethylaminopyrimidine; by similar methods a - (p - chlorophenyl) - a (4-chloro - 5 - p - chlorobenzeneazo - 2 - dimethylamino - 6 - pyrimidylamino) - acetophenone is obtained from a - amino - a - (p - chlorophenyl)-acetophenone, the latter compound being prepared by treating p-chlorobenzylphenyl ketone with butyl nitrite and acid, and reducing the a - nitroso - p - chlorobenzylphenyl ketone so formed with hydrogen and palladized charcoal. In examples there are obtained by similar processes (5) ethyl 4-chloro-5-p-chlorobenzeneazo - 2 - dimethylamino - 6 - pyrimidylaminoacetate from ethyl 4-chloro-2-dimethylamino-6-pyrimidylaminoacetate (obtained by heating 4, 6-dichloro-2-dimethylaminopyrimidine with glycine ethyl ester), (6) 4-chloro-5-p-chlorobenzeneazo - 2 - dimethylamino - 6 - hydroxypyrimidine from 4 - chloro - 2 - dimethylamino - 6 - hydroxypyrimidine (obtained by heating 4-chloro-2-dimethylamino - 6 - methoxypyrimidine with hydrochloric acid); (7) 4 - chloro - 5 - -p chlorobenzeneazo - 2 - diethylamino - 6 - methylaminopyrimidine and 4 - chloro - 5 - p - chlorobenzeneazo - 6 - methylamino - 2 - piperidinopyrimidine; and (8) 4-chloro-5-p-chlorobenzeneazo - 2 - dimethylamino - 6 - pyrimidylaminoacetone starting from trichloropyrimidine and aminoacetone semicarbazone. The preparation of 2 - dimethylamino - 4 - methylamino - 5 - benzeneazo - 6 - chloropyrimidine, 2 - dimethylamino - 4 - methylamino - 5 - o-methoxybenzeneazo - 6 - chloropyrimidine, 2-dimethylamino - 4 - methylamino - 5 - p - nitrobenzeneazo - 6 - chloropyrimidine and 2 - dimethylamino - 4 - methylamino - 5 - a - naphthaleneazo - 6 - chloropyrimidine also is described. Specifications 763,042, 763,044 and 763,120 are referred to. According to the Provisional Specification the above defined alkyl and alkoxy groups may be replaced by any hydrocarbon groups.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB978252A GB763041A (en) | 1952-04-18 | 1952-04-18 | New pyrimidine derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB978252A GB763041A (en) | 1952-04-18 | 1952-04-18 | New pyrimidine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB763041A true GB763041A (en) | 1956-12-05 |
Family
ID=9878656
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB978252A Expired GB763041A (en) | 1952-04-18 | 1952-04-18 | New pyrimidine derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB763041A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3259623A (en) * | 1963-06-14 | 1966-07-05 | Olin Mathieson | Process for preparing 2-(secondary amino)-halogenopyrimidines |
| US7816353B2 (en) * | 2003-10-24 | 2010-10-19 | Exelixis, Inc. | P70S6 kinase modulators and method of use |
-
1952
- 1952-04-18 GB GB978252A patent/GB763041A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3259623A (en) * | 1963-06-14 | 1966-07-05 | Olin Mathieson | Process for preparing 2-(secondary amino)-halogenopyrimidines |
| US7816353B2 (en) * | 2003-10-24 | 2010-10-19 | Exelixis, Inc. | P70S6 kinase modulators and method of use |
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