Pyrimidines

Synthetic Route of 1445-39-2, 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. 1445-39-2, name is 2-Amino-5-iodopyrimidine. A new synthetic method of this compound is introduced below.

d) N-(3-((2-aminopyrimidin-5-yl)ethynyl)-2-fluorophenyl)-5-chloro-2-methoxypyridine-3-sulfonamide A mixture of 5-chloro-N-(3-ethynyl-2-fluorophenyl)-2-methoxypyridine-3-sulfonamide (225 mg), 5-iodopyrimidin-2-amine (190 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (22.2 mg), copper(I) iodide (12.6 mg), triethylamine (0.92 mL) and DMSO (2.34 mL) was stirred under microwave irradiation at 100 C. for 1 hr. After cooling to room temperature, the mixture was diluted with water/saturated brine and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated to give a residue. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) and subjected to ethyl acetate. The precipitate was collected by filtration and dried under reduced pressure to give the title compound (121 mg). 1H NMR (300 MHz, DMSO-d6) delta 3.93 (3H, s), 7.12-7.32 (4H, m), 7.39 (1H, t, J=6.9 Hz), 8.08 (1H, d, J=2.4 Hz), 8.42 (2H, s), 8.51 (1H, d, J=2.4 Hz), 10.48 (1H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1445-39-2, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; FUJIMOTO, Jun; LIU, Xin; KURASAWA, Osamu; TAKAGI, Terufumi; CARY, Douglas Robert; BANNO, Hiroshi; ASANO, Yasutomi; KOJIMA, Takuto; (159 pag.)US2019/169166; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 10320-42-0, 2-Chloro-5-nitropyrimidine, 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, 10320-42-0, blongs to pyrimidines compound. HPLC of Formula: C4H2ClN3O2

tert-Butyl 4-( ( 1 S ,2R )-2-(2-aminoethyl )cyclopropyl )piperidine-1-carboxylate(Intermediate 7) (600 mg, 2.2 mmol), 2-chloro-5-nitropyrimidine (427 mg, 2.6 mmol), andpotassium carbonate (460 mg, 3.3 mmol) were stirred in DMF (5 mL) at rt for 12 hrs. The5 mixture was filtered, washing with EtOAc. The resulting organic layer was washed withsaturated aqueous ammonium chloride solution (10 mL x 1), dried over MgS04, filtered, andconcentrated under reduced pressure to afford the title compound (730 mg, 85percent) as a crudeproduct to be used for the next step. LC/MS (m/z): 392 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10320-42-0, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ACTON, John, J.; EDMONDSON, Scott, D.; LIU, Ping; MILLER, Michael, W.; WOOD, Harold, B.; DUBOIS, Byron, G.; GEISS, William, B.; WO2014/52379; (2014); A1;,
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Application of 22536-61-4, Adding some certain compound to certain chemical reactions, such as: 22536-61-4, name is 2-Chloro-5-methylpyrimidine,molecular formula is C5H5ClN2, 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 22536-61-4.

To a 3-neck flask, 5.18 g (40.3 mmol) of 2-chioro- 5-methylpyrimidine, 9.26 g (46.8 mmol) of 3-biphenylboronic acid, 95 ml of 2 M aqueous solution of potassium carbonate, and 70 ml of 1 ,2-dimethoxyethane were added, and after purge with argon gas, 2.25 g (1.95 mmol) of tetrakis (triphenylphosphine) palladium (0) was added and refluxed with heating for 24 hours under argon atmosphere. The reaction solution was cooled to room temperature, the organic layer was then recovered, the solvent was removed by distillation under reduced pressure, and by performing purification using silica gel colunm chromatography (elution solution: dichloromethane), the ligand (L-b) was obtained. The obtained amount was 8.40 g (yield: 84.7percent). Identification of the compound was carried out by using ?H-NMR. The analysis data of the ligand (L-b) are shown below. ?H-NMR (400 MHz/CDC13) oe: 8.66-8.68 (m, 3H),8.39 (d, 1H), 7.70-7.72 (m, 3H), 7.56 (t, 1H), 7.46 (t, 2H),7.37 (t, 1H), 2.36 (s, 3H).

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. 22536-61-4, 2-Chloro-5-methylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY; FURUYA METAL CO., LTD.; Konno, Hideo; Sugita, Yoshiro; Ito, Takashi; (104 pag.)US2018/66001; (2018); A1;,
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Related Products of 31462-59-6, 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. 31462-59-6, name is Pyrimidine-4-carboxylic acid, molecular formula is C5H4N2O2, 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 8Intermediate 23; [0245] Thionyl chloride (3.55mL, 48.4 mmol, 3 eq) was added drop-wise to a solution of pyrimidine-4-carboxylic acid (2 g, 16.1 mmol) in EtOH (15 mL) and the resulting mixture was heated to reflux for 14 h. The mixture was then cooled to RT and made alkaline with saturated aqueous NaHC03 to pH 8. The basic solution was then extracted with EtOAc (4 x 50 mL). The combined organic layers were washed with brine (30 mL), dried over Na2S04, filtered and concentrated in vacuo to afford Intermediate 23 (1.7g, 77%). 1H NMR: (DMSO- d6) 5 9.40 (d, J= 1.0 Hz, 1H), 9.10 (d, J= 5.1 Hz, 1H), 8.05 (dd, J= 5.1, 1.3 Hz, 1H), 4.39 (q, J= 7.1 Hz, 2H), 1.35 (t, J= 7.1 Hz, 3H); MS: 153 [M + H]+; TLC: 40% hexane in EtOAc: Rf: 0.40.

According to the analysis of related databases, 31462-59-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERSEON, INC.; SHORT, Kevin, Michael; PHAM, Son, Minh; WILLIAMS, David, Charles; DATTA, Somalee; WO2011/126903; (2011); A2;,
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Related Products of 739364-95-5, 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 739364-95-5, name is 2-Methylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

(Intermediate Example 111) 2-Methylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid (2-amino-2-methylpropyl)amide 2-Methylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid (0.18 g) was suspended in dichloromethane (5 ml), and N,N-dimethylformamide (1 drop) was added thereto. The mixture was cooled to 0C, and a solution of oxalyl chloride (10 mul) in dichloromethane (3 ml) was added dropwise thereto over 10 minutes, and the mixture was stirred as such for 1 hour at 0C. Thereafter, the mixture was stirred for 5 hours at room temperature to prepare the corresponding acid chloride. 2-Amino-2-methylpropylamine (0.11 g) was dissolved in dichloromethane, and triethylamine (0.33 ml) was added thereto and cooled to -78C. The prepared acid chloride solution was added dropwise thereto over 30 minutes and stirred as such for 30 minutes. The temperature of the mixture was increased to room temperature, and the mixture was stirred for 1 hour at room temperature. Water was added thereto, and the aqueous phase was acidified by 2 N hydrochloric acid. After washing with chloroform, the aqueous phase was alkalinized by 5 N sodium hydroxide solution and extracted with chloroform. The organic phase was washed with a saturated saline solution and dried over sodium sulfate anhydrous. The product was concentrated under reduced pressure to give the title compound (0.14 g, Y.: 56%) as yellow crystals. ESI/MS (m/z): 248 (M+H)+.

According to the analysis of related databases, 739364-95-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANWA KAGAKU KENKYUSHO CO., LTD.; EP1595866; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 7752-78-5, 5-Bromo-2-methylpyrimidine, 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, Safety of 5-Bromo-2-methylpyrimidine, blongs to pyrimidines compound. Safety of 5-Bromo-2-methylpyrimidine

Into a 1 0-L 4-neck round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed a solution of 5-bromo-2-iodopyrimidine (590 g, 2.07 mol) in THE (3 L). This was followed by dropwise addition of 1 M solution of dimethyl zinc (3.11 L, 3.11 mol) with stirring at 0¡ãC. To this was added Pd(PPh3)4 (120 g, 104 mmol). The resulting solution was stirred for 3 h at 0¡ãC, then quenched by the addition of 600 mL of aqueous NH4C1. The resultingsolution was extracted with 2 x 1.5 L of ethyl acetate. The organic extracts were combined, dried over anhydrous magnesium sulfate and concentrated under vacuum. The residue was applied onto a silica gel colunm and eluted with ethyl acetate/petroleum ether (1:50) to provide 5-bromo-2-methylpyrimidine. Into a 1 0-L 4-neck round-bottom flask purged and maintained with an inert atmosphereof nitrogen was placed a solution of 5-bromo-2-methylpyrimidine (184 g, 1.06 mol) and B(iPrO) 3 (240 g, 1.28 mol) in THE/toluene (3/3 L). This was followed by the dropwise addition of a 2.5 M solution of n-BuLi (510 mL, 1.28 mol) with stirring at -78¡ãC. The resulting solution was stirred for 1 hat -78¡ãC, then quenched by the addition of 200 nit of aqueous NH4CI. The organic phase was dried and concentrated under vacuum. The aqueous phase was adjusted to pH4 with AcOH. The solid was collected by filtration and dried in an oven under reduced pressure providing (2-methylpyrimidin-5 -yl)boronic acid.

The synthetic route of 7752-78-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ACHAB, Abdelghani Abe; ALTMAN, Michael D.; DENG, Yongqi; GUZI, Timothy; KATTAR, Solomon; KATZ, Jason D.; METHOT, Joey L.; ZHOU, Hua; MCGOWAN, Meredeth; CHRISTOPHER, Matthew P.; GARCIA, Yudith; ANTHONY, Neville John; FRADERA LLINAS, Francesc Xavier; MU, Changwei; ZHANG, Sixing; ZHANG, Rong; FONG, Kin Chiu; LENG, Xiansheng; WO2014/75392; (2014); 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. 3740-92-9, name is 4,6-Dichloro-2-phenylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C10H6Cl2N2

(1) 5 g of fenclorin, 6.1 g of potassium carbonate and 2.46 g of o-fluorophenol were dissolved in 50 mL of chloroform, and the reaction was stirred at 90 C.After 4 h of reaction, it was monitored by thin layer chromatography (developing agent was petroleum ether and dichloromethane, V petroleum ether: V dichloromethane = 3:1).Stop the reaction when there is no remaining material, and cool to room temperature;(2) pouring the reaction liquid obtained in the step (1) into water,A large amount of white solid was precipitated, stirred for 4 h, and filtered with suction to give a white solid. The white solid was subjected to column chromatography.V petroleum ether: V dichloromethane = 9:1) gave 2.21 g of 4-chloro-6-(2-fluorophenoxy)-2-phenylpyrimidine (I5) in a yield of 33.48%.

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, 3740-92-9, 4,6-Dichloro-2-phenylpyrimidine.

Reference:
Patent; Hunan Agricultural Bio-technology Institute; Bai Lianyang; Deng Xile; Zheng Wenna; Zhou Xiaomao; Liu Sihong; (13 pag.)CN109897005; (2019); A;,
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Synthetic Route of 1421372-94-2, 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.1421372-94-2, name is N-(4-Fluoro-2-methoxy-5-nitrophenyl)-4-(1-methyl-1H-indol-3-yl)pyrimidin-2-amine, molecular formula is C20H16FN5O3, molecular weight is 393.3712, as common compound, the synthetic route is as follows.

3. Synthesis of intermediate 054-5 The intermediate 054-4 (400 mg, 1.02 mmol) as a raw material was dissolved in 5 mL of NMP in 100 mL three-necked flask at room temperature under a nitrogen atmosphere, followed by sequentially adding the intermediate 006-5 (400 mg, 2.37 mmol) and K2CO3 (907 mg, 6.56 mmol) into the reaction system. The reaction system was heated to 105C and carried out for 2 hours. After completion of the reaction, the reaction was cooled to room temperature, quenched by adding 30 mL of water. The reaction mixture was extracted with 30 mL of ethyl acetate three times. The organic phases were combined, washed with 30 mL of saturated brine three times, dried over anhydrous sodium sulfate and concentrated to dryness. The residue was purified by silica gel column chromatography (eluent: DCM / MeOH = 15: 1) to give 100 mg of the intermediate 054-5 (19%) as a white solid. LCMS: 519.6.

The chemical industry reduces the impact on the environment during synthesis 1421372-94-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shanghai Shaletech Technology Co., Ltd.; JIANG, Yueheng; (143 pag.)EP3216786; (2017); A1;,
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Related Products of 3001-72-7, 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 3001-72-7, name is 2,3,4,6,7,8-Hexahydropyrrolo[1,2-a]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a stirred solution of DBN (124 mg, 1 mmol) in MeCN (4 mL), a solution of methyl 4-hydroxy-4-methyl-2-pentynoate (1a; 142 mg, 1 mmol) in MeCN (3 mL) and H2O (1 mL) was added dropwise over 10 min. The reaction mixture was stirred at 20-25 C for 48 h. Solvent was evaporated in vacuo and the residue was washed with a mixture of hexane-acetone (1:1) to give the desired product 2a.

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 3001-72-7, 2,3,4,6,7,8-Hexahydropyrrolo[1,2-a]pyrimidine.

Reference:
Article; Shemyakina, Olesya A.; Volostnykh, Olga G.; Stepanov, Anton V.; Mal’Kina, Anastasiya G.; Ushakov, Igor A.; Trofimov, Boris A.; Synthesis; vol. 50; 4; (2018); p. 853 – 858;,
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Related Products of 13036-57-2, Adding some certain compound to certain chemical reactions, such as: 13036-57-2, name is 2-Chloro-4-methylpyrimidine,molecular formula is C5H5ClN2, 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 13036-57-2.

Ethyl 3-{[(2-propen-1 -yloxy)carbonyl]amino}benzoate (20.0 g, 80.24 mmol) was dissolved in 1 M LiHMDS in THF (260 mL) and cooled to 0 C. A solution containing 2-chloro-4-methylpyrimidine (10.32 g, 80.24 mmol) in 20 mL dry THF was added to the reaction mixture. The reaction was stirred at 0 C for 2 h, quenched with MeOH (100 mL), dried directly onto silica, and purified via flash chromatography EtOAc/CH2Cl2 0-100% gradient run over 60 min. The desired fractions were combined and the solvent was removed to give the title compound. 13.6 g (51 % yield) ES-LCMS m/z 332 (M+H).

According to the analysis of related databases, 13036-57-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE LLC; ADAMS, Jerry, Leroy; FAITG, Thomas; KASPAREC, Jiri; PENG, Xin; RALPH, Jeffrey; RHEAULT, Tara Renae; WATERSON, Alex Gregory; WO2011/59610; (2011); A1;,
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