Pyrimidines

Synthetic Route of 933702-55-7 ,Some common heterocyclic compound, 933702-55-7, molecular formula is C5H3ClN2O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Dissolve 2-chloropyrimidine5-carhaldehyde (0.5 g, 3.5 mmol) in chloroform (10 mL), add diethyiaminosuifur trioxide (567 mg, 3,5 mmoi), then reflux for 1 hour. Cool the mixture to ambient temperature and quench with 1-120. Separate the layers, wash the organic fraction with 1-120 (2x), dry over Mg504, filter, collect the filtrate, and concentrate the filtrate under reduced pressure to provide the title product (327 mg, 51%),

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 933702-55-7, 2-Chloropyrimidine-5-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; ESCRIBANO, Ana Maria; GONZALEZ, Maria Rosario; LAFUENTE BLANCO, Celia; MARTIN-ORTEGA FINGER, Maria Dolores; WILEY, Michael R.; (82 pag.)WO2016/187384; (2016); A1;,
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Electric Literature of 444731-75-3, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 444731-75-3, name is N-(2-Chloropyrimidin-4-yl)-N,2,3-trimethyl-2H-indazol-6-amine. A new synthetic method of this compound is introduced below.

To a stirred suspension of the product of Intermediate Example 4 (1 .0 g, 3.6 mmol) in 10 mL of CH3CN, was added 5-amino-2-methylbenzenesulfonamide (0.70 g, 3.8 mmol, 1 .Oequiv) at room temperature. The reaction mixture was heated at reflux for 3 h, then 4 M HCI in 1 ,4-dioxane (18 muL, 0.076 mmol) was added in one portion. After 20 h, the suspension was cooled to room temperature, and filtered. The resulting solid was washed with 10 mL of CH3CINI and dried in the air to yield 1.3 g (73%) of 5-({4- [(2,3-dimethyl-2H-indazol-6-yl)methylamino]-2-pyrimidinyl}amino)-2-methyl benzenesulfonamide monohydrochloride as an off-white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,444731-75-3, N-(2-Chloropyrimidin-4-yl)-N,2,3-trimethyl-2H-indazol-6-amine, and friends who are interested can also refer to it.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/20564; (2006); A1;,
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Application of 874-14-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 874-14-6, name is 1,3-Dimethyluracil, molecular formula is C6H8N2O2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

0.14 g (1.0 mmol) of 1,3-dimethyluracil was weighed and placed in a 50 ml two-neck flask equipped with a magnetic rotor and the atmosphere in the flask was replaced with argon. The following materials were added thereinto: 2.0 ml of a 1N dimethyl sulfoxide solution of sulfuric acid, 1.0 ml of a 3.0 mol/l dimethyl sulfoxide solution of trifluoromethyl iodide, 0.2 ml of a 30percent hydrogen peroxide aqueous solution and 0.3 ml of a 1.0 mol/l aqueous solution of ferric sulfate. The mixture was stirred at 40 to 50¡ãC for 20 minutes and then the resulting solution was cooled to room temperature. Formation of 1,3-dimethyl-5-trifluoromethyluracil (19F-NMR yield: 78percent) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard. 1,3-Dimethyl-5-trifluoromethyluracil was obtained as a white solid (0.12 g, yield: 44percent) by preparative thin-layer chromatography. 1H-NMR (deuterated acetone): delta3.25(s, 3H), 3.51(s, 3H), 8.23(q, JHF=1.05Hz, 1H). 13C-NMR (deuterated acetone): delta27.8, 37.6, 102.9(q, JCF=32.3Hz), 123. 8 (q, JCF=268.4Hz), 146.4 (q, JCF=5. 91Hz), 151.9, 159.5. 19F-NMR (deuterated acetone): delta-60.6. MS (m/z): 208[M]+.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 874-14-6, 1,3-Dimethyluracil.

Reference:
Patent; Tosoh Corporation; Tosoh F- Tech Inc.; SAGAMI CHEMICAL RESEARCH CENTER; EP1947092; (2008); A1;,
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With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.26032-72-4, name is 2,4-Dichloro-6-phenylpyrimidine, molecular formula is C10H6Cl2N2, molecular weight is 225.074, as common compound, the synthetic route is as follows.category: pyrimidines

To a 250 mL flask was added a mixture of 5.0 g (22.22 mmol) of Intermediate L-3, 22.09 g (51.1 mmol) of L-6, 7.68 g (55.54 mmol) of potassium carbonate, 1.28 g of Tetrakis (triphenylphosphine) palladium (1.11 mmol) were dissolved in 100 mL of tetrahydrofuran and 30 mL of water, and the mixture was heated under reflux in a nitrogen stream for 10 hours. The resultant mixture was added to 500 mL of methanol, and the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel / celite, and then an organic solvent was removed in an appropriate amount and then recrystallized from methanol to obtain Compound A-55 (12.68 g, 75% yield). The result of elemental analysis of the resulting Compound A-55 is as follows.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,26032-72-4, 2,4-Dichloro-6-phenylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Samsung SDI Co., Ltd.; Lee, Sung Jae; Kim, Byoung Gu; Kim, Young Kwan; Min, Soo Hyoun; Saw, Ju Hee; Yun, Uhn Son; (42 pag.)KR2016/19747; (2016); A;,
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Reference of 22536-65-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 22536-65-8, name is 2-Chloro-5-methoxypyrimidine, molecular formula is C5H5ClN2O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: To a solution of 1.0 eq. of VII and 1.20 eq. of a 2-halopyrimidine in H20 and dioxane was added 2.0 eq. of potassium fluoride. The mixture was subjected to microwave irradiation maintaining a reaction temperature of 120 C for 1 h. The solvent was removed in vacuo, andthe residue was purified by chromatography.

According to the analysis of related databases, 22536-65-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARBUTUS BIOPHARMA CORPORATION; COLE, Andrew, G.; DORSEY, Bruce, D.; KAKARLA, Ramesh; KULTGEN, Steven; QUINTERO, Jorge; (353 pag.)WO2018/172852; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 3680-69-1, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 3680-69-1, blongs to pyrimidines compound. Formula: C6H4ClN3

Step C: 4-Chloro-7-{[2-(trimethylsilyl) ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine To a suspension of sodium hydride (36.141 g, 903.62 mmol) in N,N-dimethylacetamide (118 mL) at -5 C. (ice/salt bath) was added a dark solution of 4-chloropyrrolo[2,3-d]pyrimidine (119.37 g, 777.30 mmol) in N,N-dimethylacetamide (237 mL) slowly. The flask and addition funnel were rinsed with N,N-dimethylacetamide (30 mL). A large amount of gas was evolved immediately. The mixture became a slightly cloudy orange mixture. The mixture was stirred at 0 C. for 60 min to give a light brown turbid mixture. To the mixture was slowly added [2-(trimethylsilyl)ethoxy]methyl chloride (152.40 g, 914.11 mmol) and the reaction was stirred at 0 C. for 1 h. The reaction was quenched by addition of 12 mL of H2O slowly. More water (120 mL) was added followed by methyl tert-butyl ether (MTBE) (120 mL). The mixture was stirred for 10 min. The organic layer was separated. The aqueous layer was extracted with another portion of MTBE (120 mL). The organic extracts were combined, washed with brine (120 mL*2) and concentrated under reduced pressure to give the crude product 4-chloro-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine as a dark oil. Yield: 85.07 g (97%); LC-MS: 284.1 (M+H)+. It was carried to the next reaction without purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3680-69-1, its application will become more common.

Reference:
Patent; Incyte Corporation; Vaddi, Krishna; US2015/246046; (2015); A1;,
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Synthetic Route of 51940-64-8, Adding some certain compound to certain chemical reactions, such as: 51940-64-8, name is Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate,molecular formula is C7H6Cl2N2O2, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 51940-64-8.

General method for synthesis of 2-amino-4-chloropyrimidine-5-carboxylate: To a stirred solution of ethyl 2,4-dichloropyrimidine-5-carboxylate (1.6 g, 7.24 mmol) in 1,4- dioxane (15 mL) at 0-5 C under argon, ammonium hydroxide (28-30%, 2.56 mL, 21.72 mmol) is added slowly and the resulting mixture is stirred from 0 C to RT for 2 h. The reaction is complete based on TLC (30% EA/Hex, Rf = 0.3 for ethyl 2-amino-4-chloropyrimidine-5-carboxylate (Hinge-1); Rf = 0.5 for ethyl 4-amino-2-chloropyrimidine- 5-carboxylate) and LC-MS analysis. The mixture is partitioned between ethyl acetate and water. The organic layer is washed with brine, dried over Na2S04 and filtered. The filtrate is mixed with silica gel and then concentrated in vacuo. The residue is loaded to the top of silica gel packed in a glass column and eluted with 0-100% ethyl acetate/hexanes to afford ethyl 2-amino-4-chloropyrimidine-5-carboxylate (Hinge-1).[00669] The other regio isomer, ethyl 4-amino-2-chloropyrimidine-5-carboxylate, is also isolated.

According to the analysis of related databases, 51940-64-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INFINITY PHARMACEUTICALS INC.; INTELLIKINE, LLC; CASTRO, Alfredo, C.; EVANS, Catherine, A.; JANARDANANNAIR, Somarajannair; LESCARBEAU, Andre; LIU, Tao; SNYDER, Daniel, A.; TREMBLAY, Martin, R.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; WO2013/12915; (2013); A1;,
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With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.1780-26-3, name is 2-Methyl-4,6-dichloropyrimidine, molecular formula is C5H4Cl2N2, molecular weight is 163.0047, as common compound, the synthetic route is as follows.COA of Formula: C5H4Cl2N2

Example 7; Preparation of 7-(4-chlorophenyl)-5-methyl-8-(pyridin-4-yl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one; A. Preparation of 4-chloro-6-hydrazinyl-2-methylpyrimidine; To a stirred solution of 4,6-dichloro-2-methylpyrimidine (1.63 g, 10.0 mmol) in THF (25 mL) at room temperature under argon was added H2NNH2 (0.64 g, 20.0 mmol). The reaction mixture was stirred at room temperature under argon overnight. Analysis by HPLC/MS indicated that the reaction was complete. The solvent was evaporated, and the residue was coevaporated with toluene (2¡Á5 mL) then THF (5 mL), and then dried under vacuum. The crude title compound was used directly in the next step. HPLC/MS: retention time=0.77 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1780-26-3, 2-Methyl-4,6-dichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Wu, Gang; Mikkilineni, Amarendra B.; Sher, Philip M.; Murugesan, Natesan; Gu, Zhengxiang; US2006/287341; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2927-71-1, 2,4-Dichloro-5-fluoropyrimidine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Formula: C4HCl2FN2, blongs to pyrimidines compound. Formula: C4HCl2FN2

A solution of 3-nitroaniline and 2,4-dichloro-5-fluoro-pyrimidine in MeOH was stirred for 2 hours at 70 C. The mixture was diluted with water and the resulting precipitate was filtered to give 2-chloro-N4-(3-nitrophenyl)-5-fluoro-2,4-pyrimidineamine as a pale brown solid. 1H NMR (DMSO): delta 10.34 (s, 1H), 8.73 (d, 1H, J=2.4 Hz), 7.66-8.29 (m, 4H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2927-71-1, 2,4-Dichloro-5-fluoropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; Singh, Rajinder; Argade, Ankush; Payan, Donald; Molineaux, Susan; Holland, Sacha; Clough, Jeffrey; Keim, Holger; Bhamidipati, Somasekhar; Sylvain, Catherine; Li, Hui; Rossi, Alexander; US2015/266828; (2015); A1;,
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Synthetic Route of 55583-59-0, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 55583-59-0, name is 2,5-Diamino-4,6-dichloropyrimidine. A new synthetic method of this compound is introduced below.

In a reaction vessel, 4,6-dichloropyrimidine-2,5-diamine (358 mg, 2.00 mmol), 5′-m-terphenylboronic acid (1.22 g, 4.45 mmol), sodium carbonate (1.06 g) Add ethanol (5 mL) and distilled water (5 mL) to a solution of 10.0 mmol) and tetrakis (triphenylphosphine) palladium (0) (116 mg, 0.100 mmol) in toluene (20 mL) at After stirring for 20 hours under heating and reflux conditions under an argon atmosphere, the reaction solution was cooled to room temperature. Distilled water (5 mL) was added and stirred, and the separated aqueous layer was extracted three times with ethyl acetate (10 mL). Thereafter, the whole organic layer is combined, saturated aqueous sodium chloride solution (10 mL) is added thereto, the mixture is stirred and washed, anhydrous sodium sulfate is added to the separated organic layer for dehydration and the filtrate after filtration is concentrated under reduced pressure The The concentrate thus obtained is purified by flash column chromatography (silica gel, n-hexane / ethyl acetate),4,6-Di ([1,1 ‘: 3′, 1′-terphenyl] -5’-yl) pyrimidine-2,5-diamine(1.01 g, 90% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,55583-59-0, 2,5-Diamino-4,6-dichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Microbial Chemistry Research Foundation; Kumagai, Naoya; Noda, Hidetoshi; Asada, Yasuko; Shibazaki, Masakatsu; (48 pag.)JP2019/64981; (2019); A;,
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