Pyrimidines

Synthetic Route of 145783-15-9, 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. 145783-15-9, name is 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine, molecular formula is C7H9Cl2N3S, 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.

(1) 570g compound II and 2500g water are mixed, then with stirring, add in batches 756g sodium bicarbonate. After completion of addition, while stirring add in batches 350g compound I. Then heat to 100 C. Stir the reaction for 20h, the reaction solution becomes dark red muddy shape, stop heating, cooling to 40 C the following, the reaction product is added to 1000 ml ethyl acetate, stirring 5 min later, the liquid, aqueous phase for the 500 ml ethyl acetate extraction a, combined organic phase, the organic phase by adding 100 ml normal heptane, stirring to wash-out when a large amount of white solid, continue to stir 1h, filtered, get white solid compound III, product after drying 554g, yield of 88.3%, purity of 99.8%;

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 145783-15-9, 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine.

Reference:
Patent; Chengdu Huayu Pharmaceutical Co., Ltd.; Luo, Chaobin; Wan, Jiulei; (7 pag.)CN105669681; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 147118-37-4 , The common heterocyclic compound, 147118-37-4, name is N-(4-(4-Fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide, molecular formula is C16H18FN3O3S, 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.

Example 10: Preparation of Methyl 7-[4-(4-flouropheny.)-6-isopropyl-2-(N-methyl- N-methylsulfonylamino)-pyrimidin-5-yl] – (3R)-3hydroxy-5-oxo-(E)-6-heptenate (Rosuvastatin intermediate)A solution of 25 g 4-(4-flourophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonyl amino)-5-pyrimidine carbaldehyde, 55 g Methyl (3R)-3-(t-butyldimethylsilyloxy)-5-oxo- 6-triphenyl phosphoranylidene hexanoate and acetonitrile was refluxed for about 20 hrs. The reaction mass was concentrated under vacuum. To this cyclohexane was added. The reaction mass was stirred and filtered. Filtrate was Concentrated under u/v and taken into acetonitrile, cooled to 0 C. To this solution of hydrogen fluoride (100 ml) was added drop wise in acetonitrile under ice cooling, and the mixture was warmed to room temperature and stirred for 1-3 hrs. To this a mixture of DM water and dichloromethane was added and neutralized with sodium bicarbonate solution. The reaction mixture was stirred and layers were separated. The organic layer was washed with water and brine solution. To the concentrated IPA was added, stirred, and filtered. The obtained solid was washed IPE and dried to give Methyl 7-[4-(4-flourophenyl)-6-isopropyl-2-(N-methyl-N- methylsulfonylamino)-pyrimidin-5-yl] – (3R)-3-hydroxy-5-oxo-(E)-6-heptenate(32 g).

The synthetic route of 147118-37-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MATRIX LABORATORIES LTD.; SETHI, Madhuresh, Kumar; MAHAJAN, Sanjay; RAWAT, Vijendra, Singh; MARA, Bhairaiah; VEERA, Upendra, Nath; DATTA, Debashish; WO2011/141934; (2011); A1;,
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Pyrimidine – Wikipedia

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 1193-22-2, name is 4-Amino-6-hydroxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 4-Amino-6-hydroxypyrimidine

Step three, the above-mentioned 4-amino-6-hydroxypyridine and sodium acetate added to the water quality amino-6-hydroxy-pyrimidine and water ratio of 1: 15,4- amino-6-hydroxypyridine and sodium acetate in molar ratio of 1: 4, was heated to 70 , 2- chloroacetaldehyde solution was added slowly, the concentration of the aqueous solution of 2-chloro-acetaldehyde was 30%, 4-amino-6-hydroxypyridine and 2-chloroacetaldehyde the molar ratio of 1: 4, the reaction was stirred for 5 hours, cooled to room temperature, filtered and the solid washed with 30ml of water, 40 dried to give 4-hydroxy-pyrrolopyrimidine in 89% yield;

With the rapid development of chemical substances, we look forward to future research findings about 1193-22-2.

Reference:
Patent; Shanghai Titan Technology Co., Ltd; Xie, Yingbo; Zhang, Qing; Zhang, Hua; Xu, Xiaobing; Luo, Guiyun; (7 pag.)CN105218554; (2016); A;,
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The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 3993-78-0, name is 2-Amino-4-chloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 2-Amino-4-chloropyrimidine

5-Methoxy-1H-pyrrolo[3,2-b]pyridine (201-20) (200 mg, 1.35 mmol, 1 eq), cesium carbonate (877.5 mg, 2.7 mmol, 2 eq) and 4-chloropyrimidin-2-amine (203-20) (261 mg, 2.025 mmol, 1.5 eq) were mixed in N-methylpyrrolidone (5 mL). The mixture was heated to 150C and stirred to react for 2 hours. After the reaction was completed, the temperature was lowered to room temperature, and the reaction mixture was quenched with water, filtered and the residue was washed with water, dried in vacuum to give a gray solid (300 mg, yield: 92.13%). LCMS (ESI): m/z 242[M + H]+.

With the rapid development of chemical substances, we look forward to future research findings about 3993-78-0.

Reference:
Patent; Guangzhou Bebetter Medicine Technology Co., Ltd.; CAI, Xiong; QIAN, Changgeng; WENG, Yunwo; LIU, Bin; WANG, Yanyan; LIN, Mingsheng; LI, Junqi; QING, Yuanhui; YOU, Huajin; ZHOU, Shiqing; XUE, Weicai; (76 pag.)EP3345900; (2018); A1;,
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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. 61727-33-1, name is 5-Chloro-2-(methylthio)pyrimidine-4-carboxylic acid. A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Chloro-2-(methylthio)pyrimidine-4-carboxylic acid

Example 5 Methyl 7-[2-(difluoromethoxy)phenyl]-2-(methylsulfanyl)thieno[3,2-d]pyrimidine-6-carboxylate A mixture of 780 mg of 2-(difluoromethoxy)benzaldehyde and 300 mg of 5-chloro-2-(methylsulfanyl)pyrimidine-4-carboxylic acid 1 in 15 ml of anisole is microwave-heated at 130 C. for 45 min and then again for 15 min and again at 140 C. for 15 min. 160 mg of 5-chloro-2-(methylsulfanyl)pyrimidine-4-carboxylic acid 1 is then added and the mixture is again heated at 130 C. for 30 min. The mixture is concentrated under vacuum and purified on 40 g of silica, elution being carried out with 0-10% of ethyl acetate in heptane, so as to obtain 268 mg of [5-chloro-2-(methylsulfanyl)pyrimidin-4-yl][2-(difluoromethoxy)phenyl]methanol 6 in the form of a colourless oil.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 61727-33-1, 5-Chloro-2-(methylthio)pyrimidine-4-carboxylic acid.

Reference:
Patent; SANOFI; CARRY, Jean-Christophe; CHATREAUX, Fabienne; DEPRETS, Stephanie; DUCLOS, Olivier; LEROY, Vincent; MALLART, Sergio; MELON-MANGUER, Dominique; MENDEZ-PEREZ, Maria; VERGNE, Fabrice; US2013/261106; (2013); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 3438-46-8, name is 4-Methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. name: 4-Methylpyrimidine

[0375] This reaction was conducted in the same jacketed, 49 L reactor equipped with retreat curve agitator, nitrogen purge system, bottom valve for removal of a lower portion of the contents, and Dean-Stark trap and condenser system. The reactor was first purged with nitrogen. Afterward, 20% potassium t-butoxide in THF (21.06 Kg, 37.54 mol) was charged to the reactor under N2 using a cannula system. This solution was then cooled to 0 C., and the reactor was next charged with 4-methylpyrimidine (4) (1.53 Kg, 16.27 mol) while maintaining the temperature of the reactor contents at from 0 to 5 C. Immediately afterward, the Boc-protected ethyl isonipecotate (3) prepared as shown in Part A (3.99 Kg, 15.51 mol) was charged neat over 30 minutes while continuing to maintain the reactor contents at a temperature of from 0 to 5 C. Afterward, the reactor contents were stirred for 3 hours while being maintained at 5 C. The temperature of the reactor contents was then increased to 10 C., and then maintained at that temperature for 1 hour. Subsequently, 33% aqueous acetic acid solution (6.71 Kg, 36.88 mol) was charged to the reaction mixture while maintaining the reaction mixture at below 30 C. After stirring the resulting mixture for 30 minutes, it was allowed to stand for 30 minutes. The aqueous layer was then separated. Afterward, ammonium chloride solution (2.96 Kg, 3.87 mol) was charged to the reactor. The resulting mixture was stirred for 30 minutes. After allowing the mixture to stand for 30 minutes, the aqueous layer was separated. The THF was removed from the organic remaining layer by slowly raising the batch temperature under vacuum (200 torr) until the temperature reached 60-65 C. using a distillation apparatus. The final concentrate was in the form of an amber oil. This oil and toluene (12.22 Kg, 132.6 mol) were combined in the reactor, and the resulting mixture was stirred at room temperature for 15 minutes. Afterward, water (4.01 kg, 222.5 mol) was added to the reactor, and stirring was continued for an additional 30 minutes at room temperature. The reactor contents were allowed to stand for 60 minutes. The aqueous layer was then separated. The top layer (i.e., the organic layer) was then used as is to prepare the hydrazone in Part C. [TABLE-US-00002] TABLE 2 Reaction Summary for Part B materials MW equiv. wt (kg) moles density (g/mL) volume (L) potassium t-butoxide 112.2 2.42 21.06 37.54 0.902 23.3 in THF (20%) compound (3) 257.3 1.00 3.99 15.51 1.034 3.86 compound (4) 94.11 1.05 1.53 16.27 1.031 1.48 33% acetic acid 60.05 2.40 6.71 36.88 1.049 6.4 solution 7% ammonium 53.49 0.25 2.96 3.87 chloride solution toluene 92.14 10.20 12.22 132.6 0.865 14.1 water 18.02 14.35 4.01 222.5 1.000 4.01

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 3438-46-8, 4-Methylpyrimidine.

Reference:
Patent; Allen, Kimberley C.; Anderson, Dennis K.; Baldus, John E.; Boehlow, Todd; Clark, Jerry D.; Dukesherer, Daniel R.; Edney, Albert D.; Fevig, Tom; Kundra, Sastry; Lawson, Jon P.; Lau, Patrick H.; McDermott, Lisa L.; Mao, Michael K.; Moe, Jodi L.; Mudipalli, Partha; Naing, Win; Selness, Shaun R.; Seymour, Christine B.; Schilke, Tobin C.; Viswanath, Shekhar; Walker, John K.; Yalamanchili, Gopichand; US2003/225108; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1480-96-2, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 1480-96-2 as follows.

43b2-Methoxy-5-fluorouracil (43a, 1.04g, 7.21 mmol) and N,N-dimethylaniline (1.80 mL) were heated in POCI3 at 11O0C for 90 minutes. After cooling, the reaction was added carefully to ice. The product was extracted with diethylether. The ether layer was washed with sequentially with 2N HCI, water, and brine followed by drying (MgSO4). The ether was carefully removed under reduced pressure to give 43b as a volatile liquid (0.39g, 34%) which was used without further purification. Rf = 0.26 (10% EtOAc/hexane). 1H NMR (400MHz, DMSO-d6): delta 3.91 (s, 3H), 8.79 (s, 1 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1480-96-2, its application will become more common.

Reference:
Patent; PFIZER INC.; WO2006/72831; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 7504-94-1, 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. 7504-94-1, name is 2-Hydrazinylpyrimidine. A new synthetic method of this compound is introduced below.

After adding 24 mg of 2-hydrazinopyrimidine and 0.030 ml of triethylamine to a 1 ml DMF solution containing 100 mg of {2-(3-hydroxymethyl-5-methoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester (Example (11e)), the mixture was stirred at 85 C. for 14 hours and 30 minutes under a nitrogen atmosphere. The reaction mixture was concentrated, and the residue was dissolved in 1 ml of methanol, 1 ml of THF and 0.050 ml of acetic acid. After adding 100 mg of sodium cyanotrihydroborate to the reaction mixture, it was stirred at room temperature for 21 hours and 30 minutes. The reaction mixture was crudely purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% acetic acid) to give a crude product. To a solution of the obtained crude product in 3 ml of a methanol:water:acetic acid=1:1:1 mixed solvent there was added 150 mg of iron powder, and the mixture was stirred at 60 C. for 17 hours under a nitrogen atmosphere. After filtering the reaction mixture, it was purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% acetic acid) to give the title compound (28.50 mg). 1H-NMR (CD3OD) delta 1.95 (s, 3H) 3.78 (s, 3H) 4.58 (s, 2H) 5.68 (s, 1H) 6.87 (d, J=8.8 Hz, 2H) 6.91 (s, 1H) 7.03 (s, 1H) 7.13 (s, 1H) 7.35 (t, J=4.8 Hz, 1H) 7.61 (d, J=8.8 Hz, 2H) 8.78 (d, J=4.8 Hz, 2H) Mass spectrum (ESI) m/z: 447 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7504-94-1, 2-Hydrazinylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2008/15199; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 34171-40-9, Adding some certain compound to certain chemical reactions, such as: 34171-40-9, name is 2,4-Dichloro-5-ethylpyrimidine,molecular formula is C6H6Cl2N2, 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 34171-40-9.

To a mixture of 2-[[7-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indazol-1-yl]methoxy]ethyltrimethylsilane (2 g, 3.57 mmol) and 2,4-dichloro-5-ethylpyrimidine (947.53 mg, 5.36 mmol) in DME (25 mL) and H2O (5 mL) was added Pd(dppf)Cl2 (261.09 mg, 357.00 umol) and K2CO3 (986.33 mg, 7.14 mmol) in one portion at 20 C under N2. The mixture was stirred at 80 C for 2 h. The mixture was poured into water (100 mL) and extracted with EA (50 mL*2). The combined organic phase was washed with brine (100 mL*2), dried with anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by silica gel chromatography (PE/EA=100/1,40/1) to give 2-[[3-(2-chloro-5-ethylpyrimidin-4-yl)-7-fluoroindazol-1-yl]methoxy]ethyltrimethylsilane (600 mg, crude) as colorless oil. LCMS: M+H+: 407.1 1.087 min (5-95% ACN in H2O, 1.5 min).

According to the analysis of related databases, 34171-40-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MARINEAU, Jason, J.; ZAHLER, Robert; CIBLAT, Stephane; WINTER, Dana, K.; KABRO, Anzhelika; ROY, Stephanie; SCHMIDT, Darby; CHUAQUI, Claudio; MALOJCIC, Goran; PIRAS, Henri; WHITMORE, Kenneth, Matthew; LUND, Kate-Iyn; SINKO, Bill; SPROTT, Kevin; (418 pag.)WO2018/13867; (2018); A1;,
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Pyrimidine – Wikipedia

Application of 4316-98-7, Adding some certain compound to certain chemical reactions, such as: 4316-98-7, name is 6-Chloro-4,5-diaminopyrimidine,molecular formula is C4H5ClN4, 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 4316-98-7.

6B. 6-Chloro-7,9-dihydropurin-8-oneA mixture of the 5,6-diamino-4-chloropyrimidine of Example 6A (1.0 g, 6.92 mmol) and N,N’-carbonyldiimidazole (2.13 g, 13.2 mmol) in 1,4-dioxane (20 ml) was refluxed under argon for 48 hours. The solution was concentrated to a brown oil, which was triturated and washed with dichloromethane to give an off-white solid (1.02 g, 86%) LC/MS (LCTl): Rt2.45 [M+H]+ 173, 171.

According to the analysis of related databases, 4316-98-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; THE INSTITUTE OF CANCER RESEARCH:ROYAL CANCER HOSPITAL; CANCER RESEARCH TECHNOLOGY LIMITED; ASTRAZENECA AB; WO2007/125325; (2007); A1;,
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