CH644109A5 - Synthese de l'isopropylamino-2 pyrimidine. - Google Patents
Synthese de l'isopropylamino-2 pyrimidine. Download PDFInfo
- Publication number
- CH644109A5 CH644109A5 CH494480A CH494480A CH644109A5 CH 644109 A5 CH644109 A5 CH 644109A5 CH 494480 A CH494480 A CH 494480A CH 494480 A CH494480 A CH 494480A CH 644109 A5 CH644109 A5 CH 644109A5
- Authority
- CH
- Switzerland
- Prior art keywords
- pyrimidine
- synthesis
- yield
- isopropylamine
- solvent
- Prior art date
Links
- 238000003786 synthesis reaction Methods 0.000 title claims 9
- 230000015572 biosynthetic process Effects 0.000 title claims 8
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title claims 7
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 6
- FOEMIZSFFWGXHX-UHFFFAOYSA-N 2-methylsulfanylpyrimidine Chemical compound CSC1=NC=CC=N1 FOEMIZSFFWGXHX-UHFFFAOYSA-N 0.000 claims 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 5
- 239000000460 chlorine Substances 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- 238000007098 aminolysis reaction Methods 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- FTCYIGBVOHNHCD-UHFFFAOYSA-N isaxonine Chemical compound CC(C)NC1=NC=CC=N1 FTCYIGBVOHNHCD-UHFFFAOYSA-N 0.000 claims 4
- 238000010992 reflux Methods 0.000 claims 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 230000005587 bubbling Effects 0.000 claims 3
- OIGXNHYFKZCTCH-UHFFFAOYSA-N 2-methylsulfonylpyrimidine Chemical compound CS(=O)(=O)C1=NC=CC=N1 OIGXNHYFKZCTCH-UHFFFAOYSA-N 0.000 claims 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 239000007832 Na2SO4 Substances 0.000 claims 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000012074 organic phase Substances 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims 2
- 235000011152 sodium sulphate Nutrition 0.000 claims 2
- 238000004809 thin layer chromatography Methods 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical compound ClC1=NC=CC=N1 UNCQVRBWJWWJBF-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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 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
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 235000015320 potassium carbonate Nutrition 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims 1
- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 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 (1)
| Publication Number | Publication Date |
|---|---|
| CH644109A5 true CH644109A5 (fr) | 1984-07-13 |
Family
ID=10506281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH494480A CH644109A5 (fr) | 1979-07-04 | 1980-06-27 | Synthese de l'isopropylamino-2 pyrimidine. |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US4266058A (forum.php) |
| JP (1) | JPS6054312B2 (forum.php) |
| AR (1) | AR222393A1 (forum.php) |
| AT (1) | AT375072B (forum.php) |
| AU (1) | AU529586B2 (forum.php) |
| BE (1) | BE883751A (forum.php) |
| CA (1) | CA1132563A (forum.php) |
| CH (1) | CH644109A5 (forum.php) |
| DE (1) | DE3025419C2 (forum.php) |
| DK (1) | DK287480A (forum.php) |
| EG (1) | EG14820A (forum.php) |
| ES (1) | ES8105717A1 (forum.php) |
| FI (1) | FI66356C (forum.php) |
| FR (1) | FR2460937A1 (forum.php) |
| GR (1) | GR69276B (forum.php) |
| HK (1) | HK32584A (forum.php) |
| IE (1) | IE49932B1 (forum.php) |
| IL (1) | IL60234A (forum.php) |
| IN (1) | IN154499B (forum.php) |
| LU (1) | LU82517A1 (forum.php) |
| MA (1) | MA18890A1 (forum.php) |
| MX (1) | MX6162E (forum.php) |
| NL (1) | NL8003616A (forum.php) |
| NO (1) | NO802004L (forum.php) |
| NZ (1) | NZ194017A (forum.php) |
| OA (1) | OA06607A (forum.php) |
| PT (1) | PT71477A (forum.php) |
| SE (1) | SE435178B (forum.php) |
| SG (1) | SG50383G (forum.php) |
| ZA (1) | ZA803340B (forum.php) |
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 |
| HU206337B (en) * | 1988-12-29 | 1992-10-28 | Mitsui Petrochemical Ind | Process for producing pyrimidine derivatives and pharmaceutical compositions |
| US5264435A (en) * | 1988-12-29 | 1993-11-23 | Mitsui Petrochemical Industries, Ltd. | Pyrimidines and their pharmaceutical acceptable salts, and their use as medicines |
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 FI FI801817A patent/FI66356C/fi not_active IP Right Cessation
- 1980-06-05 IL IL60234A patent/IL60234A/xx unknown
- 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 NZ NZ194017A patent/NZ194017A/xx unknown
- 1980-06-11 LU LU82517A patent/LU82517A1/fr unknown
- 1980-06-12 AT AT0310580A patent/AT375072B/de not_active IP Right Cessation
- 1980-06-23 US US06/162,114 patent/US4266058A/en not_active Expired - Lifetime
- 1980-06-23 NL NL8003616A patent/NL8003616A/nl not_active Application Discontinuation
- 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 JP JP55088001A patent/JPS6054312B2/ja not_active Expired
- 1980-06-30 IE IE1355/80A patent/IE49932B1/en unknown
- 1980-07-01 MA MA19087A patent/MA18890A1/fr unknown
- 1980-07-01 PT PT71477A patent/PT71477A/pt unknown
- 1980-07-01 MX MX808898U patent/MX6162E/es unknown
- 1980-07-02 AR AR281619D patent/AR222393A1/es active
- 1980-07-03 NO NO802004A patent/NO802004L/no unknown
- 1980-07-03 DK DK287480A patent/DK287480A/da unknown
- 1980-07-03 CA CA355,324A patent/CA1132563A/en not_active Expired
- 1980-07-04 AU AU60113/80A patent/AU529586B2/en not_active Ceased
- 1980-07-04 DE DE3025419A patent/DE3025419C2/de not_active Expired
- 1980-07-04 OA OA57154A patent/OA06607A/xx unknown
- 1980-07-04 FR FR8014890A patent/FR2460937A1/fr active Granted
- 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
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |