DE3025419C2 - Verfahren zur Synthese von 2-Isopropylamino-pyrimidin - Google Patents
Verfahren zur Synthese von 2-Isopropylamino-pyrimidinInfo
- Publication number
- DE3025419C2 DE3025419C2 DE3025419A DE3025419A DE3025419C2 DE 3025419 C2 DE3025419 C2 DE 3025419C2 DE 3025419 A DE3025419 A DE 3025419A DE 3025419 A DE3025419 A DE 3025419A DE 3025419 C2 DE3025419 C2 DE 3025419C2
- Authority
- DE
- Germany
- Prior art keywords
- pyrimidine
- synthesis
- yield
- isopropylamino
- isopropylamine
- 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
- 230000015572 biosynthetic process Effects 0.000 title claims description 9
- 238000003786 synthesis reaction Methods 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims 8
- FTCYIGBVOHNHCD-UHFFFAOYSA-N isaxonine Chemical compound CC(C)NC1=NC=CC=N1 FTCYIGBVOHNHCD-UHFFFAOYSA-N 0.000 title claims 5
- 239000002904 solvent Substances 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 5
- OIGXNHYFKZCTCH-UHFFFAOYSA-N 2-methylsulfonylpyrimidine Chemical compound CS(=O)(=O)C1=NC=CC=N1 OIGXNHYFKZCTCH-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 238000007098 aminolysis reaction Methods 0.000 claims 4
- FOEMIZSFFWGXHX-UHFFFAOYSA-N 2-methylsulfanylpyrimidine Chemical compound CSC1=NC=CC=N1 FOEMIZSFFWGXHX-UHFFFAOYSA-N 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 claims 2
- KVJHGPAAOUGYJX-UHFFFAOYSA-N 1,1,3,3-tetraethoxypropane Chemical compound CCOC(OCC)CC(OCC)OCC KVJHGPAAOUGYJX-UHFFFAOYSA-N 0.000 claims 1
- UZEKTDVGUQCDBI-UHFFFAOYSA-N 2-propan-2-ylguanidine Chemical compound CC(C)NC(N)=N UZEKTDVGUQCDBI-UHFFFAOYSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 239000007900 aqueous suspension Substances 0.000 claims 1
- 230000005587 bubbling Effects 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 238000003408 phase transfer catalysis Methods 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7923224 | 1979-07-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3025419A1 DE3025419A1 (de) | 1981-01-15 |
| DE3025419C2 true DE3025419C2 (de) | 1985-12-12 |
Family
ID=10506281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3025419A Expired DE3025419C2 (de) | 1979-07-04 | 1980-07-04 | Verfahren zur Synthese von 2-Isopropylamino-pyrimidin |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US4266058A (en:Method) |
| JP (1) | JPS6054312B2 (en:Method) |
| AR (1) | AR222393A1 (en:Method) |
| AT (1) | AT375072B (en:Method) |
| AU (1) | AU529586B2 (en:Method) |
| BE (1) | BE883751A (en:Method) |
| CA (1) | CA1132563A (en:Method) |
| CH (1) | CH644109A5 (en:Method) |
| DE (1) | DE3025419C2 (en:Method) |
| DK (1) | DK287480A (en:Method) |
| EG (1) | EG14820A (en:Method) |
| ES (1) | ES8105717A1 (en:Method) |
| FI (1) | FI66356C (en:Method) |
| FR (1) | FR2460937A1 (en:Method) |
| GR (1) | GR69276B (en:Method) |
| HK (1) | HK32584A (en:Method) |
| IE (1) | IE49932B1 (en:Method) |
| IL (1) | IL60234A (en:Method) |
| IN (1) | IN154499B (en:Method) |
| LU (1) | LU82517A1 (en:Method) |
| MA (1) | MA18890A1 (en:Method) |
| MX (1) | MX6162E (en:Method) |
| NL (1) | NL8003616A (en:Method) |
| NO (1) | NO802004L (en:Method) |
| NZ (1) | NZ194017A (en:Method) |
| OA (1) | OA06607A (en:Method) |
| PT (1) | PT71477A (en:Method) |
| SE (1) | SE435178B (en:Method) |
| SG (1) | SG50383G (en:Method) |
| ZA (1) | ZA803340B (en:Method) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4661303A (en) * | 1985-06-11 | 1987-04-28 | The Dow Chemical Company | Reactive coextrusion of functionalized polymers |
| US5264435A (en) * | 1988-12-29 | 1993-11-23 | Mitsui Petrochemical Industries, Ltd. | Pyrimidines and their pharmaceutical acceptable salts, and their use as medicines |
| HU206337B (en) * | 1988-12-29 | 1992-10-28 | Mitsui Petrochemical Ind | Process for producing pyrimidine derivatives and pharmaceutical compositions |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2586844A (en) * | 1947-10-21 | 1952-02-26 | Ayerst Mckenna & Harrison | Preparation of delta2-1, 3-diazacycloalkenes |
| GB1523274A (en) * | 1974-08-05 | 1978-08-31 | Ici Ltd | Herbicidal compositions containing substituted pyrimidine |
-
1980
- 1980-06-04 ZA ZA00803340A patent/ZA803340B/xx unknown
- 1980-06-04 IN IN414/DEL/80A patent/IN154499B/en unknown
- 1980-06-05 IL IL60234A patent/IL60234A/xx unknown
- 1980-06-05 FI FI801817A patent/FI66356C/fi not_active IP Right Cessation
- 1980-06-06 GR GR62136A patent/GR69276B/el unknown
- 1980-06-10 BE BE0/200985A patent/BE883751A/fr not_active IP Right Cessation
- 1980-06-11 LU LU82517A patent/LU82517A1/fr unknown
- 1980-06-11 NZ NZ194017A patent/NZ194017A/xx unknown
- 1980-06-12 AT AT0310580A patent/AT375072B/de not_active IP Right Cessation
- 1980-06-23 NL NL8003616A patent/NL8003616A/nl not_active Application Discontinuation
- 1980-06-23 US US06/162,114 patent/US4266058A/en not_active Expired - Lifetime
- 1980-06-24 SE SE8004659A patent/SE435178B/sv not_active IP Right Cessation
- 1980-06-25 ES ES492747A patent/ES8105717A1/es not_active Expired
- 1980-06-27 CH CH494480A patent/CH644109A5/fr not_active IP Right Cessation
- 1980-06-30 IE IE1355/80A patent/IE49932B1/en unknown
- 1980-06-30 JP JP55088001A patent/JPS6054312B2/ja not_active Expired
- 1980-07-01 PT PT71477A patent/PT71477A/pt unknown
- 1980-07-01 MA MA19087A patent/MA18890A1/fr unknown
- 1980-07-01 MX MX808898U patent/MX6162E/es unknown
- 1980-07-02 AR AR281619D patent/AR222393A1/es active
- 1980-07-03 CA CA355,324A patent/CA1132563A/en not_active Expired
- 1980-07-03 DK DK287480A patent/DK287480A/da unknown
- 1980-07-03 NO NO802004A patent/NO802004L/no unknown
- 1980-07-04 OA OA57154A patent/OA06607A/xx unknown
- 1980-07-04 AU AU60113/80A patent/AU529586B2/en not_active Ceased
- 1980-07-04 FR FR8014890A patent/FR2460937A1/fr active Granted
- 1980-07-04 DE DE3025419A patent/DE3025419C2/de not_active Expired
- 1980-07-05 EG EG398/80A patent/EG14820A/xx active
-
1983
- 1983-08-13 SG SG50383A patent/SG50383G/en unknown
-
1984
- 1984-04-12 HK HK325/84A patent/HK32584A/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2929596A1 (de) | Verfahren zur herstellung von oxoalkyl-xanthinen | |
| CH564551A5 (en:Method) | ||
| DE2056569C3 (en:Method) | ||
| DE3025419C2 (de) | Verfahren zur Synthese von 2-Isopropylamino-pyrimidin | |
| EP0098422A2 (de) | Verfahren zur Herstellung von 4-Hydroxy-2-methyl-N-2-pyridyl-2H-1,2-benzothiazin-3-carboxamid 1,1-dioxid | |
| DE1906401A1 (de) | Verfahren zur Herstellung von 4-Acyloxy-azetidin-2-onen | |
| DD140041B1 (de) | Verfahren zur herstellung von langkettigen n-alkyldimethylmorpholinen | |
| CH642365A5 (de) | Verfahren zur herstellung von 6-piperidino-2,4-diaminopyrimidin-3-oxid. | |
| DE2302970C3 (de) | Verfahren zur Herstellung von 4-(1-subst.-4-piperidyliden)-4H-benzo [4,5] cyclohepta [1,2-b] thiophen-10(9H)-onen | |
| DE2545569B2 (de) | 1,3-dithiacyclopenten-2-ylidenmalonsaeuredialkylester, verfahren zu deren herstellung und diese enthaltende fungizide mittel | |
| CH645098A5 (de) | Verfahren zur herstellung von n-cyan-n'-methyl-n''-(2-mercaptoaethyl)guanidin. | |
| DE1545581A1 (de) | Neue Penicillinaldehyde und Verfahren zu deren Herstellung | |
| DE531083C (de) | Verfahren zur Darstellung von 5,6-Dialkoxy-8-aminochinolinen | |
| DE737931C (de) | Verfahren zur Herstellung von 2, 4-Diaminochinazolin | |
| DE1259872B (de) | Verfahren zur Herstellung von Sulfonylurethanen bzw. deren Salzen | |
| DE2350395C3 (de) | N-(m-Trifluormethylthiophenyl)-piperazin, deren Salze, Verfahren zu deren Herstellung und deren Verwendung als Zwischenverbindung zur Herstellung von Piperazin-Derivaten | |
| DE1002318B (de) | Verfahren zur Herstellung von bakteriostatisch wirksamen Oxamidsaeureestern | |
| DE613402C (de) | Verfahren zur Darstellung von 4-Pyridylpyridiniumdichlorid | |
| AT230378B (de) | Verfahren zur Herstellung von neuen diquartären α,ω-Bis-[pyridyl-(4)-thio]-alkanen und -dialkyläthern | |
| DE1545721C (de) | Verfahren zur Herstellung von 1 (2 Alkyl 4 ammo 5 pyrimidyl methyl) pyri dinium Verbindungen | |
| DE1174305B (de) | Verfahren zur Herstellung von ª‡-substituierten ª‰-Oxypropionsaeurelactonen | |
| EP0206293A2 (de) | Verfahren zur Herstellung von 3,5-Dichlor-2-pyridon | |
| DE1219494B (de) | Verfahren zur Herstellung von DL-2, 2-Dialkyl-5-amino-6-phenyl-dioxanen-(1, 3) | |
| DE1049379B (de) | Verfahren zur Herstellung von 4 - (tert.-Aminoalkylmercapto)chinolinverbindungen | |
| DE1186069B (de) | Verfahren zur Herstellung von N, N'-disubstituierten Piperazinen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8125 | Change of the main classification |
Ipc: C07D239/42 |
|
| 8181 | Inventor (new situation) |
Free format text: DEMOSTENE, CLAUDE, ARAMON, FR ASPISI, CHRISTIAN, BOULBON, FR |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |