DE2310334A1 - Verfahren zur herstellung von teilweise neuen 4,6-dichlorpyrazolo-(3,4-d)-pyrimidinderivaten - Google Patents
Verfahren zur herstellung von teilweise neuen 4,6-dichlorpyrazolo-(3,4-d)-pyrimidinderivatenInfo
- Publication number
- DE2310334A1 DE2310334A1 DE19732310334 DE2310334A DE2310334A1 DE 2310334 A1 DE2310334 A1 DE 2310334A1 DE 19732310334 DE19732310334 DE 19732310334 DE 2310334 A DE2310334 A DE 2310334A DE 2310334 A1 DE2310334 A1 DE 2310334A1
- Authority
- DE
- Germany
- Prior art keywords
- pyrimidine
- solution
- preparation
- methanol
- pyrazolo
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 3
- CTYPROOLWJDUTA-UHFFFAOYSA-N 4,6-dichloro-1h-pyrazolo[3,4-d]pyrimidine Chemical class ClC1=NC(Cl)=C2C=NNC2=N1 CTYPROOLWJDUTA-UHFFFAOYSA-N 0.000 title description 7
- 238000006243 chemical reaction Methods 0.000 claims description 8
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- KVJIRFGNHAAUNQ-UHFFFAOYSA-N 2,4,6-trichloropyrimidine-5-carbaldehyde Chemical compound ClC1=NC(Cl)=C(C=O)C(Cl)=N1 KVJIRFGNHAAUNQ-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229940045348 brown mixture Drugs 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- OEICGMPRFOJHKO-UHFFFAOYSA-N 2-(ethoxymethylidene)propanedinitrile Chemical compound CCOC=C(C#N)C#N OEICGMPRFOJHKO-UHFFFAOYSA-N 0.000 description 1
- XGGAWFDOIDZRPI-UHFFFAOYSA-N 4,6-Dihydroxy Natural products C1=C2OCOC2=CC(C2OC(C3C(OC(O)C32)C=2C=C3OCOC3=CC=2)O)=C1 XGGAWFDOIDZRPI-UHFFFAOYSA-N 0.000 description 1
- DUFGYCAXVIUXIP-UHFFFAOYSA-N 4,6-dihydroxypyrimidine Chemical compound OC1=CC(O)=NC=N1 DUFGYCAXVIUXIP-UHFFFAOYSA-N 0.000 description 1
- YMXQUFUYCADCFL-UHFFFAOYSA-N 4-chloro-1h-pyrazolo[3,4-d]pyrimidine Chemical compound ClC1=NC=NC2=C1C=NN2 YMXQUFUYCADCFL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- NHOWLEZFTHYCTP-UHFFFAOYSA-N benzylhydrazine Chemical compound NNCC1=CC=CC=C1 NHOWLEZFTHYCTP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D239/30—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT179472A AT328414B (de) | 1972-03-03 | 1972-03-03 | Verfahren zur herstellung von 4,6-dichlor-pyrazolo- (3,4-d) -pyrimidin bzw. dessen neuen 1-aryl- oder 1-aralkylderivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2310334A1 true DE2310334A1 (de) | 1973-09-13 |
Family
ID=3521108
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732310334 Pending DE2310334A1 (de) | 1972-03-03 | 1973-03-01 | Verfahren zur herstellung von teilweise neuen 4,6-dichlorpyrazolo-(3,4-d)-pyrimidinderivaten |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS4899194A (enExample) |
| AT (1) | AT328414B (enExample) |
| DD (1) | DD103242A5 (enExample) |
| DE (1) | DE2310334A1 (enExample) |
| FR (1) | FR2181784A1 (enExample) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4507146A (en) * | 1982-12-28 | 1985-03-26 | Ciba-Geigy Corporation | 2,4-Diamino-6-halo-5-trifluoromethylpyrimidines having herbicidal activity |
| EP0271804A3 (en) * | 1986-12-19 | 1989-08-23 | Bayer Ag | Cyano-trichloro-pyridopyrimidine |
| US4918169A (en) * | 1987-08-27 | 1990-04-17 | Ciba-Geigy Corporation | Fiber-reactive dyestuffs comprising a 5-formylpyrimidine moiety |
| US4952679A (en) * | 1987-08-27 | 1990-08-28 | Ciba-Geigy Corporation | Fiber-reactive dyes containing a 5-formylpyrimidine moiety |
| US4968781A (en) * | 1987-04-02 | 1990-11-06 | Ciba-Geigy Corporation | Fiber-reactive dyes comprising a halopyrimidine for which a vinylsulfonyl or the like moiety is attached via a bridge member |
| WO2006128954A1 (en) * | 2005-06-01 | 2006-12-07 | Fermion Oy | Process for the preparation of n-[4-(4-fluorophenyl)-5-formyl-6-isopropyl-pyrimidin-2-yl]-n-methylmethanesulfonamide |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2123654A4 (en) | 2006-12-28 | 2011-05-11 | Taisho Pharmaceutical Co Ltd | pyrazolopyrimidine compound |
-
1972
- 1972-03-03 AT AT179472A patent/AT328414B/de not_active IP Right Cessation
-
1973
- 1973-01-22 DD DD16838073A patent/DD103242A5/xx unknown
- 1973-02-28 JP JP2337273A patent/JPS4899194A/ja active Pending
- 1973-03-01 DE DE19732310334 patent/DE2310334A1/de active Pending
- 1973-03-02 FR FR7307478A patent/FR2181784A1/fr not_active Withdrawn
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4507146A (en) * | 1982-12-28 | 1985-03-26 | Ciba-Geigy Corporation | 2,4-Diamino-6-halo-5-trifluoromethylpyrimidines having herbicidal activity |
| EP0271804A3 (en) * | 1986-12-19 | 1989-08-23 | Bayer Ag | Cyano-trichloro-pyridopyrimidine |
| US4968781A (en) * | 1987-04-02 | 1990-11-06 | Ciba-Geigy Corporation | Fiber-reactive dyes comprising a halopyrimidine for which a vinylsulfonyl or the like moiety is attached via a bridge member |
| US4918169A (en) * | 1987-08-27 | 1990-04-17 | Ciba-Geigy Corporation | Fiber-reactive dyestuffs comprising a 5-formylpyrimidine moiety |
| US4952679A (en) * | 1987-08-27 | 1990-08-28 | Ciba-Geigy Corporation | Fiber-reactive dyes containing a 5-formylpyrimidine moiety |
| WO2006128954A1 (en) * | 2005-06-01 | 2006-12-07 | Fermion Oy | Process for the preparation of n-[4-(4-fluorophenyl)-5-formyl-6-isopropyl-pyrimidin-2-yl]-n-methylmethanesulfonamide |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2181784A1 (en) | 1973-12-07 |
| DD103242A5 (enExample) | 1974-01-12 |
| JPS4899194A (enExample) | 1973-12-15 |
| AT328414B (de) | 1976-03-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DD140040A5 (de) | Verfahren zur herstellung von 5-alkylthio-pyrimidinen | |
| DE2310334A1 (de) | Verfahren zur herstellung von teilweise neuen 4,6-dichlorpyrazolo-(3,4-d)-pyrimidinderivaten | |
| DE1904894A1 (de) | Verfahren zur Herstellung von Pyrazolo-(3,4-d)-pyrimidinen | |
| EP0001760B1 (de) | Alpha-aminomethylen-beta-formylaminopropionitril, Verfahren zu seiner Herstellung sowie Verwendung zur Herstellung von 2-Methyl-4-amino-5-formylaminomethyl-pyrimidin | |
| WO2001040229A2 (de) | Verfahren zur herstellung von epinastine-hydrochlorid in der hochschmelzenden kristallmodifikation | |
| DE2018345A1 (de) | Verfahren zur Herstellung von Pyrazolo-(3,4-d)-pyrimidinen | |
| DE2511599B2 (de) | 3,7-Dihydro-5-phenyl-6-methyl- pyrrole [3,4-e] [1,4] gleich diazepin-2 (lH)-one, Verfahren zu ihrer Herstellung und Arzneimittel | |
| DE2122070A1 (de) | 1 Veratryl 4 methyl 5 athyl 7,8 dimethoxy 2,3 diazabicyclo eckige Klam mer auf 5,4,0 eckige Klammer zu undeca pentaen (1,3,6,8,10) und seine Verwendung | |
| DE1948924C3 (de) | 13-Diallyl-4-chlor-5-äthyl-uracil und Verfahren zu dessen Herstellung | |
| DE2352107A1 (de) | Neue chemische verbindungen, deren herstellungsverfahren und anwendungen dieser verbindungen, insbesondere auf die synthese 2,4-diamino-(3',4',5'-trimethoxy-) 1-benzyl-pyrimidin | |
| DE2065698B2 (de) | Verfahren zur Herstellung von 2-Isopropyl-6-methyl-4(3H)-pyrimidon | |
| DE864555C (de) | Verfahren zur Herstellung von 2, 4-Diamino-5-aryloxypyrimidinen | |
| DE1620301A1 (de) | Verfahren zur Herstellung von 2-substiutierten Cycloheptimidazolderivaten | |
| DE2242162A1 (de) | Neue pyrimidopyrimidinderivate und verfahren zu ihrer herstellung | |
| DE2014978A1 (de) | Pyrido eckige Klammer auf 2,3 d eckige Klammer zu pynmidin 4(3H) one und Verfahren zur Herstellung derselben | |
| DE1817761C3 (de) | 2-Aminomethyl-3-phenyl-5-nitroindole und ihre Salze | |
| DE1795053A1 (de) | Verfahren zur Herstellung von Verbindungen der Benzodiazepinreihe | |
| DE889151C (de) | Verfahren zur Herstellung von 2, 4-Diamino-5-phenyl-pyrimidin-abkoemmlingen | |
| DE1067030B (de) | Verfahren zur Her stellung von 4,6 disubsütuierten 1-Pyra zolo (3 4-d) pynmidmen | |
| DE1768582A1 (de) | Verfahren zur Herstellung von 2,3-Dichlor-4-butyrylphenoxyessigsaeure | |
| DD264439A1 (de) | Verfahren zur herstellung von 2,5,7-substituierten s-triazolo(1,5-a)pyrimidin-6-carbaldehyden | |
| DE1670055A1 (de) | Verfahren zur Herstellung heterocyclischer Verbindungen | |
| DE1695893B1 (de) | Verfahren zur Herstellung von 4-Amino-5-acylamidomethylpyrimidinen | |
| DE2714253A1 (de) | Herstellung von isoxazolo- eckige klammer auf 3,4-d eckige klammer zu -pyrimidinen und sie enthaltende arzneimittel | |
| DE3842062A1 (de) | Explosionssichere 1-dimethylamino-3-dimethylimino-2-arylpropen-1-salze, verfahren zu ihrer herstellung und ihre verwendung |