RO86363B - Procedeu pentru prepararea unor derivati de metiltiopirimidina - Google Patents
Procedeu pentru prepararea unor derivati de metiltiopirimidinaInfo
- Publication number
- RO86363B RO86363B RO109750A RO10975083A RO86363B RO 86363 B RO86363 B RO 86363B RO 109750 A RO109750 A RO 109750A RO 10975083 A RO10975083 A RO 10975083A RO 86363 B RO86363 B RO 86363B
- Authority
- RO
- Romania
- Prior art keywords
- group
- general formula
- phenyl
- alkoxyalkyl
- alkenyl
- Prior art date
Links
- FOEMIZSFFWGXHX-UHFFFAOYSA-N 2-methylsulfanylpyrimidine Chemical class CSC1=NC=CC=N1 FOEMIZSFFWGXHX-UHFFFAOYSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- DDWBEROMBZXLNB-UHFFFAOYSA-N 2,4,6-trichloro-5-methylsulfanylpyrimidine Chemical compound CSC1=C(Cl)N=C(Cl)N=C1Cl DDWBEROMBZXLNB-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 abstract 1
- 229910000105 potassium hydride Inorganic materials 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 229910052717 sulfur Chemical group 0.000 abstract 1
- 239000011593 sulfur Chemical group 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- 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
- C07D239/60—Three or more oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Inven#355;ia se refera la un procedeu de preparare a unor derivati de metiltiopirimidina cu formula generala i:(vezi formula) în care R1 este o grupa alchil avînd de la 1 la 6 atomi de carbon sau o grupa fenil, benzil, alchenil sau alcoxialchil; R2 reprezinta o grupare alchil de la 1 la 6 atomi de carbon, fenil, fenil substituit cu halogen, alchenil, alchenil omegafenil substituit, alchinil, alcoxialchil, alcoxicarbonil amonialchil, alcoxialcoxialchil, alchiltioalchil, tetreahidrofuril sau o grupa în care r3 si R4 reprezinta în mod individual un atom de hidrogen sau o grupa metil, Y este hidrogen sau halogen, metil sau metoxi, n reprezinta un numar întreg, 1 sau 2 si X reprezinta oxigen sau sulf. Procedeul consta în aceea ca (a) 5-metiltio-2,4,6-triclor-pirimidina reactioneaza cu 2 echivalenti din compusul cu formula generala Ii: R1-OH în care R1 are semnificatiile de mai sus, în prezenta unei baze aleasa din grupul constînd din metal alcalin; hidrura de sodiu, hidrura de potasiu, hidroxide metal alcalin si compusii analogi, la o temperatura cuprinsa între -10 degree C si punctul de fierbere al solventului, în calitate de solvent fiind folosit cel putin unul ales din grupul constînd din tetrahidrofuran, dioxan tilfosfortriamida, benzen, toluen, ater si chiar alcoolul R1-OH astfel încît sa formeze un derivat cu formula generala III: (vezi formula) în care R1 are aceeasi semnificatie ca mai sus ; (b) derivatul dialcoxipirimidinic reactioneaza apoi cu un compus cu formula generala IV: R2XH în care R2 are semnificatiile de mai sus în prezenta aceluiasi baze indicate mai sus.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57006142A JPS58124773A (ja) | 1982-01-20 | 1982-01-20 | ５−メチルチオピリミジン誘導体とその製造法と農園芸用殺菌剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RO86363A RO86363A (ro) | 1985-03-15 |
| RO86363B true RO86363B (ro) | 1985-03-31 |
Family
ID=11630260
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RO83116657A RO89716A (ro) | 1982-01-20 | 1983-01-17 | Compozitie fungicida lichida |
| RO83116655A RO89714A (ro) | 1982-01-20 | 1983-01-17 | Procedeu de preparare a unor derivati de 5-metiltiopirimidina |
| RO83116656A RO89715A (ro) | 1982-01-20 | 1983-01-17 | Compozitie fungicida solida |
| RO109750A RO86363B (ro) | 1982-01-20 | 1983-01-17 | Procedeu pentru prepararea unor derivati de metiltiopirimidina |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RO83116657A RO89716A (ro) | 1982-01-20 | 1983-01-17 | Compozitie fungicida lichida |
| RO83116655A RO89714A (ro) | 1982-01-20 | 1983-01-17 | Procedeu de preparare a unor derivati de 5-metiltiopirimidina |
| RO83116656A RO89715A (ro) | 1982-01-20 | 1983-01-17 | Compozitie fungicida solida |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4540698A (ro) |
| JP (1) | JPS58124773A (ro) |
| DD (2) | DD219654A5 (ro) |
| DE (1) | DE3301106A1 (ro) |
| FR (1) | FR2519983B1 (ro) |
| GB (1) | GB2113216B (ro) |
| IN (1) | IN157931B (ro) |
| IT (1) | IT1163039B (ro) |
| NL (1) | NL8300193A (ro) |
| PL (1) | PL138343B1 (ro) |
| RO (4) | RO89716A (ro) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59227867A (ja) * | 1983-06-09 | 1984-12-21 | Mitsui Toatsu Chem Inc | ５―メチルチオピリミジン誘導体とその製造法と農園芸用殺菌剤 |
| JPH0635450B2 (ja) * | 1984-03-16 | 1994-05-11 | 三井東圧化学株式会社 | チオシアノピリミジン誘導体、その製造法および農園芸用殺菌剤 |
| JPS6345269A (ja) * | 1986-04-28 | 1988-02-26 | Mitsui Toatsu Chem Inc | ジハロゲン置換チオシアノピリミジン誘導体、その製造法および農園芸用殺菌剤 |
| JPS63112566A (ja) * | 1986-10-28 | 1988-05-17 | Nissan Chem Ind Ltd | ピリミジノン誘導体、その製法および殺虫・殺ダニ・殺菌剤 |
| JPH0827122A (ja) * | 1994-07-15 | 1996-01-30 | Kureha Chem Ind Co Ltd | ２−（ベンジルオキシ）（フェノキシ）ピリミジン誘導体、その製造方法及び除草剤 |
| RU2194040C2 (ru) * | 1996-10-31 | 2002-12-10 | Кумиай Кемикал Индастри Ко., Лтд. | Производные пиримидинилоксиалканамидов и фунгициды для сельского хозяйства или садоводства |
| US6660731B2 (en) * | 2000-09-15 | 2003-12-09 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| KR20030032035A (ko) * | 2000-09-15 | 2003-04-23 | 버텍스 파마슈티칼스 인코포레이티드 | 단백질 키나제 억제제로서 유용한 피라졸 화합물 |
| US7473691B2 (en) * | 2000-09-15 | 2009-01-06 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| MXPA03005610A (es) | 2000-12-21 | 2003-10-06 | Vertex Pharma | Compuestos de pirazol utiles como inhibidores de la proteina cinasa. |
| RU2004126671A (ru) * | 2002-02-06 | 2005-04-10 | Вертекс Фармасьютикалз Инкорпорейтед (Us) | Гетероарилсоединения, полезные в качестве ингибиторов gsk-3 |
| AU2003218215A1 (en) * | 2002-03-15 | 2003-09-29 | Vertex Pharmaceuticals, Inc. | Azolylaminoazines as inhibitors of protein kinases |
| MY141867A (en) * | 2002-06-20 | 2010-07-16 | Vertex Pharma | Substituted pyrimidines useful as protein kinase inhibitors |
| KR20050032105A (ko) * | 2002-08-02 | 2005-04-06 | 버텍스 파마슈티칼스 인코포레이티드 | Ｇｓｋ-3의 억제제로서 유용한 피라졸 조성물 |
| US7601718B2 (en) * | 2003-02-06 | 2009-10-13 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of protein kinases |
| US7592340B2 (en) * | 2003-12-04 | 2009-09-22 | Vertex Pharmaceuticals Incorporated | Quinoxalines useful as inhibitors of protein kinases |
| AU2006279376B2 (en) * | 2005-08-18 | 2011-04-14 | Vertex Pharmaceuticals Incoporated | Pyrazine kinase inhibitors |
| BRPI0619706A2 (pt) * | 2005-11-03 | 2011-10-11 | Vertex Pharma | composto, composição, método para inibir a atividade da proteìna aurora quinase numa amostra biológica, método para tratar um distúrbio proliferativo num paciente, método para tratar cáncer num indivìduo |
| DE602007004750D1 (de) * | 2006-11-02 | 2010-03-25 | Vertex Pharma | Als inhibitoren von proteinkinasen geeignete aminopyridine und aminopyrimidine |
| WO2008077086A1 (en) * | 2006-12-19 | 2008-06-26 | Vertex Pharmaceuticals Incorporated | Aminopyrimidines useful as inhibitors of protein kinases |
| NZ579483A (en) * | 2007-03-09 | 2012-07-27 | Vertex Pharma | Aminopyridines useful as inhibitors of protein kinases |
| AU2008226466B2 (en) * | 2007-03-09 | 2013-06-13 | Vertex Pharmaceuticals Incorporated | Aminopyrimidines useful as inhibitors of protein kinases |
| JP5520057B2 (ja) * | 2007-03-09 | 2014-06-11 | バーテックス ファーマシューティカルズ インコーポレイテッド | 蛋白キナーゼの阻害剤として有用なアミノピリミジン |
| AU2008240313A1 (en) | 2007-04-13 | 2008-10-23 | Aj Park | Aminopyrimidines useful as kinase inhibitors |
| AU2008247592A1 (en) | 2007-05-02 | 2008-11-13 | Vertex Pharmaceuticals Incorporated | Thiazoles and pyrazoles useful as kinase inhibitors |
| CA2688584A1 (en) * | 2007-05-02 | 2008-11-13 | Vertex Pharmaceuticals Incorporated | Aminopyrimidines useful as kinase inhibitors |
| WO2008137621A1 (en) * | 2007-05-02 | 2008-11-13 | Vertex Pharmaceuticals Incorporated | Aminopyrimidines useful as kinase inhibitors |
| CA2687966A1 (en) * | 2007-05-24 | 2008-12-04 | Vertex Pharmaceuticals Incorporated | Thiazoles and pyrazoles useful as kinase inhibitors |
| CN101790532B (zh) * | 2007-07-31 | 2013-11-20 | 沃泰克斯药物股份有限公司 | 5-氟-1H-吡唑并[3，4-b]吡啶-3-胺及其衍生物的制备方法 |
| EP2323622A1 (en) * | 2008-09-03 | 2011-05-25 | Vertex Pharmaceuticals Incorporated | Co-crystals and pharmaceutical formulations comprising the same |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4199583A (en) * | 1970-07-13 | 1980-04-22 | The Upjohn Company | Antifungal method, formulations and compounds |
| US4126459A (en) * | 1976-05-14 | 1978-11-21 | Polaroid Corporation | Thioether substituted silver halide solvents |
| US4211559A (en) * | 1976-09-30 | 1980-07-08 | Texas Instruments Incorporated | Photographic processes and compositions employing thioether containing silver halide solvents |
-
1982
- 1982-01-20 JP JP57006142A patent/JPS58124773A/ja active Granted
-
1983
- 1983-01-04 IN IN14/CAL/83A patent/IN157931B/en unknown
- 1983-01-07 GB GB08300400A patent/GB2113216B/en not_active Expired
- 1983-01-14 DE DE19833301106 patent/DE3301106A1/de not_active Withdrawn
- 1983-01-14 US US06/457,917 patent/US4540698A/en not_active Expired - Fee Related
- 1983-01-17 RO RO83116657A patent/RO89716A/ro unknown
- 1983-01-17 RO RO83116655A patent/RO89714A/ro unknown
- 1983-01-17 RO RO83116656A patent/RO89715A/ro unknown
- 1983-01-17 RO RO109750A patent/RO86363B/ro unknown
- 1983-01-18 IT IT19164/83A patent/IT1163039B/it active
- 1983-01-18 PL PL1983240209A patent/PL138343B1/pl unknown
- 1983-01-19 DD DD83260099A patent/DD219654A5/de unknown
- 1983-01-19 DD DD83247352A patent/DD209447A5/de unknown
- 1983-01-19 NL NL8300193A patent/NL8300193A/nl not_active Application Discontinuation
- 1983-01-20 FR FR8300880A patent/FR2519983B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| RO89715A (ro) | 1986-07-30 |
| RO89716A (ro) | 1986-07-30 |
| IT1163039B (it) | 1987-04-08 |
| DE3301106A1 (de) | 1983-07-28 |
| GB2113216B (en) | 1985-12-04 |
| DD209447A5 (de) | 1984-05-09 |
| DD219654A5 (de) | 1985-03-13 |
| PL240209A1 (en) | 1984-06-18 |
| NL8300193A (nl) | 1983-08-16 |
| IN157931B (ro) | 1986-07-26 |
| FR2519983B1 (fr) | 1985-12-06 |
| IT8319164A0 (it) | 1983-01-18 |
| FR2519983A1 (fr) | 1983-07-22 |
| GB8300400D0 (en) | 1983-02-09 |
| RO86363A (ro) | 1985-03-15 |
| GB2113216A (en) | 1983-08-03 |
| JPS58124773A (ja) | 1983-07-25 |
| US4540698A (en) | 1985-09-10 |
| JPH0378383B2 (ro) | 1991-12-13 |
| RO89714A (ro) | 1986-07-30 |
| PL138343B1 (en) | 1986-09-30 |
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