Tag: M.W:200-300

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. 113583-35-0, name is 2-Methanesulfonyl-4,6-dimethoxypyrimidine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Methanesulfonyl-4,6-dimethoxypyrimidine

Add (10mmol) salicylaldehyde, (10mmol) 4,6-dimethoxy-2-methylsulfonylpyrimidine, (20mmol) potassium carbonate powder, and 30ml DMF into a 100ml three-necked flask equipped with a reflux condenser. Gradually heat to 60C, stir the reaction for 1 to 3 hours, and track the reaction to the end by TLC.Stop the reaction, transfer the reaction system to 100ml of water while it is hot, and stir it fully to precipitate a white or light yellow solid, with a yield of 92%, mp 91-92C, without purification, and directly used in the next reaction.

The synthetic route of 113583-35-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xi’an Modern Chemical Institute; Wang Wei; Wang Lieping; Li Bingbo; Zhang Xiaoguang; Liu Kangyun; Ning Binke; Xue Chao; (10 pag.)CN111269223; (2020); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 58347-48-1 ,Some common heterocyclic compound, 58347-48-1, molecular formula is C10H10ClN3O2, 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.

To a solution of ethyl 7-chloro-5-methylpyrazolo[l,5-a]pyrimidine-3-carboxylate (1.0 g, 4.18 mmol) in toluene (10 mL) was added (Bu3Sn)20 (5.0 g, 8.36 mmol). The reaction mixture was stirred at 120 C for 2 days, and concentrated in vacuo. The residue was dissolved in EtOAc (10 mL), and basified with sat. aHC03solution (10 mL) to pH~8-9. The aqueous phase was separated and acidified with 6N HC1 (10 mL) to pH~5. The solution was extracted with EtOAc (10 mL x 3). The organic phases were dried over anhydrous Na2S04, and filtered. The filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (PE/EA; 1 : 1) to give 7-chloro-5-methylpyrazolo[l,5-a]pyrimidine-3- carboxylic acid (230 mg, 26%) as a white solid. LC-MS m/z: 211.0 [M+H]+, Purity (214 nm): >97%, tR= 1.23min.

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. 58347-48-1, Ethyl 7-chloro-5-methylpyrazolo[1,5-a]pyrimidine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; LANSBURY, Peter, T.; GOOD, Andrew, C.; BOURQUE, Elyse, Marie Josee; (139 pag.)WO2016/73895; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 33097-11-9, 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. 33097-11-9, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbaldehyde, molecular formula is C6H4Cl2N2OS, 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 stirred solution of aldehyde 1 (1.0mmol, 1equiv) in 3mL DMF was added enamine 2 (1.15equiv) followed by addition of a few drops of satd ethereal HCl. (0027) Except for 6d: Mixture was stirred at ambient temperature for period of time indicated in Table 1. After removing of solvent (50C/5 Torr) the residue was stirred with water (10mL) for 1h, crystals were filtered and dried at 110C/5 Torr to give compound 6 with purity?94%. Recrystallization from DMF can be used for purification, if necessary. (0028) For 6d: After stirring for 20h the additional portion of enamine 4d (0.15equiv) was added and the mixture was left at ambient temperature for 4 days. After removing of solvent (50C/5 Torr) the residue was dissolved in CHCl3 (30mL), washed with water, satd NaHCO3 and brine. Compound 6d was isolated using column chromatography on silica (EtOAc-nHexane 1:1, Rf?0.25).

According to the analysis of related databases, 33097-11-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chizhova, Maria E.; Bakulina, Olga Yu.; Ivanov, Alexander Yu.; Lobanov, Pavel S.; Dar’in, Dmitrii V.; Tetrahedron; vol. 71; 36; (2015); p. 6196 – 6203;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 90213-67-5, 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 90213-67-5, name is 2,4-Dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

(2S,35)-ethyl 3 -aminobicyclo[2.2.2]octane-2-carboxylate hydrochloride (1.26 g, 5.40 mmol) and 2,4-dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (1.10 g, 5.40 mmol) were dissolved in DMF (5 mL), then potassium carbonate (1.50 g, 11.00 mmol) was added. The mixture was stirred at rt overnight. Water (50 mL) was added to quench the reaction, and the resulting mixture was extracted with EtOAc (50 mL x 2). The combined organic phases were washed with saturated brine (80 mL), dried over anhydrous Na2504, filtered, and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatograph (PE/EtOAc (v/v) = 10/1) to give the title compound as a yellow solid (979 mg, 50 %).MS (ESI, pos.ion) m/z: 363.2 [M+H]?H NMR (400 MHz, CDC13) (ppm): 6.87 (d, J= 3.4 Hz, 1H), 6.41 (s, 1H), 5.32 (s, 1H), 4.63 (s, 1H), 4.21 (q, J= 7.1 Hz, 2H), 3.76 (s, 3H), 2.39 (d, J 4.9 Hz, 1H), 1.96 – 1.52 (m, 1OH), 1.26 (t, J 7.0 Hz, 3H).

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 90213-67-5, 2,4-Dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; REN, Qingyun; TANG, Changhua; YIN, Junjun; YI, Kai; LEI, Yibo; WANG, Yejun; ZHANG, Yingjun; (215 pag.)WO2018/127096; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 13162-26-0, 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 13162-26-0 as follows.

Cyclopentylamine(5.2ml) and N,N-diisopropylethylamine(13.2ml) were dissolved into 150ml dichloromethane. The mixture was added dropwise to a solution of 2,4-dichloro-5-nitro-6-methylpyrimidine(10.7g) in dichloromethane(30ml) at 0C. After the completion of the dropwise addition, the mixture was kept at the same temperature to react for 1 hour. Purification was conducted by a column chromatography to obtain a bright-yellow solid(11.2g) in a yield of 84.8%. 1H NMR(400 MHz, CDCl3): delta 8.44(s, 2H), 4.41(m, 1H), 2.64(s,3H), 2.01-2.15(m, 2H), 1.61-1.76(m, 4H), 1.45-1.63(m, 2H)ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13162-26-0, its application will become more common.

Reference:
Patent; Si Chuan University; CSPC Zhongqi Pharmaceutical Technology (Shijiazhuang) Co., Ltd.; YANG, Shengyong; WEI, Yuquan; EP2578584; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 26032-72-4, Adding some certain compound to certain chemical reactions, such as: 26032-72-4, name is 2,4-Dichloro-6-phenylpyrimidine,molecular formula is C10H6Cl2N2, 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 26032-72-4.

The compound 2,4-dichloro-6-phenylpyrimidine (1.52 g, 6.7 mmol),(+/-)-trans-3-aminobicyclo[2.2.2]octane-2-carboxylic acid methyl ester(1.84 g, 10.0 mmol) was dissolved in N,N-dimethylformamide (10 mL).Potassium carbonate (0.92 g, 6.7 mmol) was then added to the reaction mixture.The resulting mixture was stirred at room temperature overnight. After the reaction is complete,It was diluted with H2O (50 mL), and the mixture was extracted with ethyl acetate (40mL×3).The combined organic phases were washed with saturated brine (50 mL).Dry with anhydrous sodium sulfate, filter, and concentrate the filtrate under reduced pressure.The residue was purified by silica gel column chromatography(n-hexane/ethyl acetate (v/v) = 20/1-10/1)The title compound was obtained as a white solid(1.65g, 66%).

According to the analysis of related databases, 26032-72-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ren Qingyun; Tang Changhua; Yin Junjun; Yi Kai; Lei Yibo; Wang Yejun; Zhang Yingjun; (138 pag.)CN108276401; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 57054-92-9, 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. 57054-92-9, name is 5-Bromo-2-chloro-4-methoxypyrimidine. A new synthetic method of this compound is introduced below.

Step Y1 : 2-(5-Bromo-4-methoxy-pyrimidin-2-ylamino)-ethanol A mixture of 5-bromo-2-chloro-4-methoxypyrimidine (5 g, 22.4 mmol) and 2-amino ethanol (1.76 mL, 29.1 mmol) in THF (50 mL) was stirred for 18 h at rt. 2-Amino ethanol (2 mL) was added. The reaction mixture was stirred for 18 h at rt and concentrated. The residue was purified by flash chromatography (hexane/EtOAc, 3:2) to afford 4.08 g of the title compound. tR: 0.70 min (LC-MS 2); ESI-MS: 248.2 [M+H]+ (LC-MS 2); Rf: 0.06 (hexane/EtOAc 3:2).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,57054-92-9, 5-Bromo-2-chloro-4-methoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; GUAGNANO, Vito; HOLZER, Philipp; KALLEN, Joerg; LIAO, Lv; MAH, Robert; MAO, Liang; MASUYA, Keiichi; SCHLAPBACH, Achim; STUTZ, Stefan; VAUPEL, Andrea; WO2013/111105; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 444731-75-3, 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.444731-75-3, name is N-(2-Chloropyrimidin-4-yl)-N,2,3-trimethyl-2H-indazol-6-amine, molecular formula is C14H14ClN5, molecular weight is 287.75, as common compound, the synthetic route is as follows.

Example 69 5-({4-[(2,3-dimethyl-2H-indazol-6-yl)(methyl)amino]pyrimidin-2-yl}amino)-2-methylbenzenesulfonamide To a solution of Intermediate Example 13 (200 mg, 0.695 mmol) and 5-amino-2-methylbenzenesulfonamide (129.4 mg, 0.695 mmol) in isopropanol (6 ml) was added 4 drops of conc. HCl. The mixture was heated to reflux overnight. The mixture was cooled to rt and diluted with ether (6 ml). Precipitate was collected via filtration and washed with ether. HCl salt of 5-({4-[(2,3-dimethyl-2H-indazol-6-yl)(methyl)amino]-pyrimidin-2-yl}amino)-2-methylbenzenesulfonamide was isolated as an off-white solid. 1H NMR (400 MHz, d6DMSO+NaHCO3) delta 9.50 (br s, 1H), 8.55 (br s, 1H), 7.81 (d, J = 6.2 Hz, 1H), 7.75 (d, J = 8.7 Hz, 1H), 7.69 (m, 1H), 7.43 (s, 1H), 7.23 (s, 2H), 7.15 (d, J = 8.4 Hz, 1H), 6.86 (m, 1H), 5.74 (d, J = 6.1 Hz, 1H), 4.04 (s, 3H), 3.48 (s, 3H), 2.61 (s, 3H), 2.48 (s, 3H). MS (ES+, m/z) 438 (M+H).

Statistics shows that 444731-75-3 is playing an increasingly important role. we look forward to future research findings about N-(2-Chloropyrimidin-4-yl)-N,2,3-trimethyl-2H-indazol-6-amine.

Reference:
Patent; Novartis AG; Boloor, Amogh; Cheung, Mui; Davis, Ronda; Harris, Philip Anthony; Hinkle, Kevin; Mook, Robert Anthony Jr; Stafford, Jeffery Alan; Veal, James Martin; EP2311825; (2015); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 4359-87-9 ,Some common heterocyclic compound, 4359-87-9, molecular formula is C4Cl3N3O2, 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.

2,4,6-Trichloro-5-nitropyrimidine (45, 1.43 g, 6.26 mmoles) was dissolved in dichloromethane and cooled to 0 C. A solution of 8-oxa-3-azabicyclo[3.2.1]octane (2, 0.934 g, 6.26 mmoles) in dichloromethane and triethylamine (0.873 ml_, 6.26 mmoles) was slowly added over 1 hour. The solution was allowed to stir at 0 C for 2 hours, then warmed to room temperature and stirred for an additional 16 hours. The reaction mixture was filtered, the filtrate was concentrated, dissolved in ethyl acetate, washed with 1 N hydrochloric acid, saturated sodium bicarbonate, brine, dried, and concentrated to provide 3-(2,6-dichloro-5-nitropyrimidin-4- yl)-8-oxa-3-azabicyclo[3.2.1]octane (46). Yield: 1.53 g (80%). HRMS; [M+H]+ Obs’d = 305.0200, [M+H]+ Calc’d = 305.0203.

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. 4359-87-9, 2,4,6-Trichloro-5-nitropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WYETH LLC; VERHEIJEN, Jeroen, Cunera; ZASK, Arie; RICHARD, David, James; KAPLAN, Joshua, Aaron; CURRAN, Kevin, Joseph; WO2010/120998; (2010); A1;,
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.130049-82-0, name is 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one, molecular formula is C11H15ClN2O2, molecular weight is 242.7, as common compound, the synthetic route is as follows.HPLC of Formula: C11H15ClN2O2

300 ml of acetonitrile was charged followed by 20.0 g of 3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido-[1,2-a]-pyrimidin-4-one and 21.0 g of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride at room temperature. The reaction mass was stirred at room temperature for 5 minutes and 20.0 g of potassium carbonate and 0.7 g of potassium iodide were charged. Further, 0.2 g of sodium borohydride was charged and the temperature was raised to 65±2 C. The reaction mass was maintained at 65±2 C. for 25 hours. After reaction completion, the reaction mass was slowly cooled to room temperature. The solids were filtered, washed with 50 ml of acetonitrile and then dissolved in 800 ml of methylene chloride at room temperature. The contents were heated to 30-35 C., maintained for 10 minutes, filtered and washed with 20 ml of methylene chloride. The clear filtrate was distilled completely under vacuum below 35 C. and replaced with 50 ml of acetone. Further, 300 ml of acetone was charged, heated to 45 C. and stirred for 30 minutes. The reaction mass was cooled to room temperature and stirred for 1 hour. The product was filtered, washed with 20 ml of acetone and dried under vacuum at 50-55 C. to yield paliperidone (30 g, yield: 150% w/w, efficiency: 85.11%, keto impurity by HPLC: 0.01%, total impurity level by HPLC: 1.0%)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,130049-82-0, 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one, and friends who are interested can also refer to it.

Reference:
Patent; CIPLA LIMITED; Puppala, Ravikumar; Pathi, Srinivas Laxminarayan; Kankan, Rajendra Narayanrao; US2014/200228; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia