Day: July 16, 2021

Electric Literature of 111196-81-7, 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.111196-81-7, name is 2-Chloro-5-ethylpyrimidine, molecular formula is C6H7ClN2, molecular weight is 142.59, as common compound, the synthetic route is as follows.

Step B: Preparation of 5-Ethyl-2-(4-(((lr,4r)-4-(2-fluoro-4- (methylsulfonyl)phenyl)cyclohexyloxy)methyl)piperidin-l-yl)pyrimidine (Compound 8).; A mixture of 4-(((lr,4r)-4-(2-fluoro-4- (methylsulfonyl)phenyl)cyclohexyloxy)methyl)piperidine hydrochloride (50.4 mg, 0.124 mmol), prepared in Step A above, 2-chloro-5-ethylpyrimidine (36 mu, 0.296 mmol), and triethylamine (52 mu, 0.373 mmol) in iPrOH (3 mL) was heated under microwave irradiation at 120 C for 2 h. The mixture was extracted with water and AcOEt. The organic phase was dried over MgS04, filtered, and concentrated. The residue was purified by silica gel flash column chromatography (hexane/ AcOEt gradient). Fractions containing the title compound (with 2- chloro-5-ethylpyrimidine as by product) were partly concentrated. The residue was treated with MTBE. Solid was filtered off, washed with additional MTBE, and dried under high vacuum to give the title compound (35.6 mg, 0.075 mmol, 60.3 % yield) as a white solid. Exact mass calculated for C25H34FN3O3S: 475.23, found: LCMS m/z = 476.2 [M+H]+; lU NMR (400 MHz, CDCI3) delta ppm 1.16-1.23 (m, 5H), 1.39-1.55 (m, 4H), 1.83-1.86 (m, 3H), 1.92-1.95 (m, 2H), 2.17-2.20 (m, 2H), 2.44 (q, = 7.6 Hz, 2H), 2.84-2.91 (m, 3H), 3.27 (s, 3H), 3.25-3.29 (m, 1H), 3.36 (d, = 6.1 Hz, 2H), 4.70-4.73 (m, 2H), 7.39-7.43 (m, 1H), 7.57-7.60 (m, 1H), 7.66-7.68 (m, 1H), 8.16 (s, 2H).

Statistics shows that 111196-81-7 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-ethylpyrimidine.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; HAN, Sangdon; LEHMANN, Juerg; THORESEN, Lars; WO2012/135570; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 302964-08-5, 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. 302964-08-5, name is 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, molecular formula is C16H13Cl2N5OS, 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.

To a mixture of the starting material 7H (150 mg, 0.38 mmol) and dioxane (8 mL) were added (S)-pyrrolidin-3-ol hydrochloride (141 mg, 1.14 mmol, 3 eq) and DIEA (245 mg, 1.90 mmol, 5 eq) at room temperature. The mixture was then stirred at 90-92 C. under nitrogen for 12 h. LC-MS analysis showed the product peak. The mixture was not a clear solution. The mixture was cooled to room temperature and concentrated to dryness under reduced pressure, and the resultant residue was suspended in 50 mL acetonitrile, and centrifuged at 4000 rpm for 15 min. The pellet was then suspended in cooled 80% acetonitrile, and centrifuged at 4000 rpm for 15 min. The pellet was re-suspended in cooled 80% acetonitrile, and centrifuged at 4000 rpm for 15 min. The supernatants were combined and concentrated to dryness to afford the target compound X (H-31) (105 mg) as an off-white solid. LC-MS: 445 (M+H); 1H NMR (DMSO-d6): 11.40 (s, 1H. NH), 9.83 (s, 1H, NH), 8.19 (s, 1H), 7.40 (m, 1H), 7.24 (m, 2H), 5.80 (s, 1H), 4.98 (s, 1H), 4.35 (s, 1H), 2.53 (s, 3H), 2.20 (s, 2H), 2.12 (s, 2H), 1.85 (m, 2H).

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 302964-08-5, 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide.

Reference:
Patent; Princeton Drug Discovery Inc; He, Kan; (37 pag.)US2018/99960; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 347418-42-2, 4-Chloro-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, Safety of 4-Chloro-5-fluoropyrimidine, blongs to pyrimidines compound. Safety of 4-Chloro-5-fluoropyrimidine

The compound 5 (1 mmol),The compound 4-chloro-5-fluoropyrimidine (1 mmol)Dissolved in NMP (10 mL)CuI (20 mmol%) was added,Pd (PPh3) 2Cl2 (5 mmol%),DIEA (5 mmol).Under nitrogen protection,60 reaction 12h.TCL monitoring reaction is complete,Extracted three times with ethyl acetate,Combine organic phase,Washed twice with saturated NaCl,Anhydrous Na2SO4 dry.Spin dry,Column chromatography gave compound 7r.

The synthetic route of 347418-42-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Second Military Medical University, PLA; Yantai Dongcheng Pharmaceutical Industry Group Co., Ltd.; Zhang, Dazhi; Jiang, Yuanying; Niting, Junhong; Cai, Zhan; Pang, Lei; Xie, Fei; Li, Ran; Han, Haibing; He, Yan; You, Shouyi; Yang, Zhenqiu; Qi, Dongqi; (36 pag.)CN106336383; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 767-15-7, 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 767-15-7, name is 2-Amino-4,6-dimethylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: For the synthesis of 2, the solution of sulfurisocyanatidic chloride (7.2mmol) in 20mL toluene was added to the solution of 1 (6.0mmol) in 20mL toluene dropwise at room temperature. The reactant was heated to 140C and then the reaction proceeded for 18h under reflux. Subsequently, the mixture was cooled down to room temperature and remaining sulfurisocyanatidic chloride was removed under reduced pressure, together with the solvent. Without further purification, the resulting yellow oil 2 was dissolved in 10mL anhydrous acetonitrile and after that it was added slowly to 5mmol of 3, which was also dissolved in 10mL anhydrous acetonitrile beforehead in ice bath. After stirring for 24hat room temperature, acetonitrile was removed under reduced pressure and saturated sodium bicarbonate was added to product 4. Product 5 precipitated easily and it was further purified by recrystallization from petroleum ether/acetone in 1:1 ratio in high yields. 15% hydrochloric acid was added to aqueous solution of 5 under stirring and corresponding acidified product 4 precipitated out easily in high yields.

According to the analysis of related databases, 767-15-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wu, Ren-Jun; Ren, Tongtong; Gao, Jie-Yu; Wang, Li; Yu, Qilin; Yao, Zheng; Song, Guo-Qing; Ruan, Wei-Bin; Niu, Cong-Wei; Song, Fu-Hang; Zhang, Li-Xin; Li, Mingchun; Wang, Jian-Guo; European Journal of Medicinal Chemistry; vol. 162; (2019); p. 348 – 363;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 939986-65-9, Adding some certain compound to certain chemical reactions, such as: 939986-65-9, name is 6-Chloropyrimidine-4-carbonitrile,molecular formula is C5H2ClN3, 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 939986-65-9.

A solution of 4-(hydroxymethyl)-1H-indazole 1 (233 mg, 1.57 mmol), 6-chloropyrimidine-4-carbonitrile (200 mg, 1.43 mmol), and DMF (4 mL) was added dropwise at RT to NaH (57 mg of a 60% dispersion in mineral oil, 1.43 mmol). The mixture was stirred at RT for 25 mm. The mixture was partitioned between aq HC1, brine, and EtOAc. The organic layer was separated, dried (Na2504), filtered, and concentrated under reduced pressure. The residue was purified (silica gel; eluting 0 to 100% EtOAc in hexanes), to afford compound 2 (162 mg, 45%) as a yellow solid. LCMS Mass: 252.0 (M+1).

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. 939986-65-9, 6-Chloropyrimidine-4-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PHARMAKEA, INC.; ROWBOTTOM, Martin, W.; HUTCHINSON, John, Howard; (185 pag.)WO2017/3862; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 5909-24-0, name is Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Formula: C8H9ClN2O2S

In THF (150 mL) was suspended 3-chloro-4-methoxybenzylamine hydrochloride salt (16.0 g, 76.9 mmol). The suspension was cooled in an ice bath, and triethylamine (19.4 g, 192.3 mmol) was added dropwisely. The reaction mixture was stirred at ambient temperature for 15 min, then was added ethyl 4-chloro-2-thiomethyl-5-pyrimidine carboxylate (14.9 g, 64.1 mmol). The reaction mixture was stirred at ambient temperature overnight. TLC was used to monitor the reaction. After the completion of the reaction, the solvent was removed by rotary evaporation. Acetic ether (500 mL) and water (200 mL) were added. The organic phase was separated, washed with hydrochloric acid (1N), saturated aqueous solution of sodium bicarbonate and brine, dried over sodium sulfate and filtrated. The filtrate was concentrated under reduced pressure. The solvent was removed by rotary evaporation to give oil. Methanol (100 mL) was added to precipitate a large amount of white solid. The mixture was filtrated and the solid was dried in vacuum to give ethyl 4-((3-chloro-4-methoxybenzyl)amine)-2-thiomethyl-5-pyrimidine carboxylate (21 g, 74.2 % yield).

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, 5909-24-0, Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; WU, Frank; WANG, Aichen; EP2886540; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1032452-86-0, name is 3-(2-Chloropyrimidin-4-yl)-1-methyl-1H-indole, the common compound, a new synthetic route is introduced below. Computed Properties of C13H10ClN3

40 g (0.164 mol) of SM1, 30.6 g (0.164 mol) of SM2 and 62.3 g (0.328 mol) of mono-p-toluenesulfonic acid monohydrate were added to 200 ml of isobutyl alcohol and warmed to reflux for 6 h. A yellow solid precipitated and dropped to After washing at room temperature, filtration, isopropanol and vacuum drying at 50 C 54.8 g of a yellow solid was obtained with a yield of 85.0%.

The synthetic route of 1032452-86-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Sihuan Pharmaceutical Co., Ltd.; Zhang Xiaojun; Liu Huimin; Guo Jianjun; Li Gang; Ning Shangen; (14 pag.)CN107216313; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 63200-54-4 , The common heterocyclic compound, 63200-54-4, name is 2,4-Dichloro-5H-pyrrolo[3,2-d]pyrimidine, molecular formula is C6H3Cl2N3, 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.

General procedure: A mixture of 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine 18a (51.3 g) and 1.36 L of 1 N NaOH was stirred at 80 C overnight. The solution was subsequently chilled and adjusted to pH 6 with AcOH. The resulting precipitate was collected, washed with water and dried to afford 19a as solid (37.3 g, yield: 80.7%).

The synthetic route of 63200-54-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xie, Hui; Zeng, Lili; Zeng, Shaogao; Lu, Xin; Zhang, Guicheng; Zhao, Xin; Cheng, Na; Tu, Zhengchao; Li, Zhiyuan; Xu, Hongjiang; Yang, Ling; Zhang, Xiquan; Huang, Min; Zhao, Junling; Hu, Wenhui; European Journal of Medicinal Chemistry; vol. 52; (2012); p. 205 – 212;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.31462-54-1, name is 2-Iodopyrimidine, molecular formula is C4H3IN2, molecular weight is 205.98, as common compound, the synthetic route is as follows.Computed Properties of C4H3IN2

Example 28 General Procedure for the Palladium-Catalyzed Cross-Coupling of ArylIodides with l -Trityl-lH-imidazol-4-yl)zinc(II) chloride; ,[0349] To a stirred solution of 4-iodo-1-trityl-lH-imidazole (218.0 mg, 0.5 mmol) in anhydrous THF (4 mL) at room temperature was added EtMgBr (1.0 M in THF, 0.5 mmol, 0.5 mL) dropwise, under an atmosphere of N2. The resulting solution was allowed to stir for 90 min and anhydrous ZnCl2 (0.5 mmol, 68.2 mg) was added. The resulting white suspension was allowed to stir for 90 min and a solution of the aryl iodide (0.5 mmol) in THF (1 mL) was added followed by the immediate addition of Pd(PPlV}) (56 mg, 0.05 mmol). The reaction mixture was allowed to stir at 70 C for 12 h under an atmosphere of N2. After cooling to room temperature, the solution was diluted with CH2C12 (10 mL) and the organic layer was washed with an EDTA (aq) buffer (pH = 9) (2 x 5 mL) and brine. The organic layer was dried (Na2SC>4) and concentrated under reduced pressure. The crude residue was used in next step without further purification. To a solution of the crude imidazole from the previous step was added trifluoroacetic acid (1.0 mL) and MeOH (4.0 mL). The solution was stirred at 80 C for 2 h. The reaction mixture was allowed to cool to room temperature and the pH was adjusted to -10 with 10% NaOH (aq). The aqueous phase was extracted with EtOAc (3 x 20 mL). The combined organic layers were washed with water, brine, and dried. The solvent was removed in vacuo to afford the crude residue, which was purified by flash column chromatography on silica gel to afford the desired product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,31462-54-1, 2-Iodopyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; NEWLINK GENETICS; MAUTINO, Mario, R.; KUMAR, Sanjeev; JAIPURI, Firoz; WALDO, Jesse; KESHARWANI, Tanay; ZHANG, Xiaoxia; WO2011/56652; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 514854-13-8, 6-Ethyl-5-iodopyrimidine-2,4-diamine, 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, 514854-13-8, blongs to pyrimidines compound. SDS of cas: 514854-13-8

According to general Sonogashira coupling procedure ethyl-iodopyrimidine (0.065 g, 0.25 mmol), CuI (0.009g, 0.049 mmol, 20mol%), Pd(PPh3)2Cl2 (0.017 g, 0.025mmol, 10mol%) and alkyne 17 (0.110 g, 0.374 mmol) were reacted in DMF/Et3N ( 1ml each) at 65C for 12 hrs. After the mixture was cooled, the dark brown solution was concentrated and the product was purified by flash chromatography (SiO2 10 g, 2% MeOH/CHC2) followed by reverse phase flash chromatography (NH2 capped SiO2, CHCl2) to afford coupled pyrimidine 19 as a pale solid (0.085 g, 80%). 1H NMR (500 MHz, CDCl3) delta 7.17 (s, 1H), 7.11 (d, J = 2.15 Hz, 1H), 7.07 (dd, J = 2.19, 8.34 Hz, 1H), 6.97 – 6.93 (m, 2H), 6.92 (d, J = 8.36 Hz, 1H), 5.19 (s, 2H), 4.96 (s, 2H), 4.29 (s, 4H), 4.05 (q, J = 7.06 Hz, 1H), 3.85 (s, 3H), 2.71 (q, J = 7.55 Hz, 2H), 1.61 d, J = 7.1Hz, 3H), 1.24 (t, J = 7.57 Hz, 3H); 13C NMR (125 MHz, CDCl3) delta 173.27, 164.26, 160.61, 160.16, 145.23, 143.63, 143.33, 142.40, 134.53, 120.15, 117.89, 117.52, 115.89, 111.15, 110.64, 101.55, 90.57, 75.40, 64.45, 64.41, 55.34, 33.14, 29.65, 24.71, 12.54; HRMS (DART, MH+) m/z 431.2093 (calculated for C25H27N4O3, 431.2083).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,514854-13-8, its application will become more common.

Reference:
Article; Paulsen, Janet L.; Viswanathan, Kishore; Wright, Dennis L.; Anderson, Amy C.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 5; (2013); p. 1279 – 1284;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia