Tag: M.W:200-300

Reference of 3740-92-9, 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.3740-92-9, name is 4,6-Dichloro-2-phenylpyrimidine, molecular formula is C10H6Cl2N2, molecular weight is 225.07, as common compound, the synthetic route is as follows.

A mixture of 80 (0.25g, 1.11mmol) and IPA (3ml) was stirred for a while and then 2M methylamine in THF (1.39ml, 2.78mmol) was added thereto at 0 °C. The resulting mixture was back to room temperature under stirring for overnight. The reaction was quenched by water and then the mixture was extracted by ethyl acetate (30ml x 3). The residue was purified by flash column over silica gel (ethyl acetate: n-Hexane = 1 :4, Rf = 0.18) to afford 84 (0.22g, 90.23percent) as a pale yellow solid. 1H-NMR (300MHz, CDCl3): delta 3.02 (d, J= 4.2 Hz, 3H), 5.09 (br, 1H), 6.26 (s, 1H), 7.42-7.46 (m, 3H), 8.35-8.37 (m, 2H).

The chemical industry reduces the impact on the environment during synthesis 3740-92-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; TAIPEI MEDICAL UNIVERSITY; YEN, Yun; LIOU, Jing-Ping; CHEN, Chun-Han; (70 pag.)WO2017/15400; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 171887-03-9, Adding some certain compound to certain chemical reactions, such as: 171887-03-9, name is N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide,molecular formula is C5H4Cl2N4O, 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 171887-03-9.

To a solution ofN-(2-amino-4,6-dichloropyrimidin-5-yl)formamide (12 g, 57 mmol) in THF (250 mL) was added Lawesson’s reagent (17.5 g, 43 mmol). The reaction mixture was stirred at 65C for 30 minutes. The reaction mixture was then filtered, and the filtrate was concentrated. The crude yellow solid obtained was triturated using diethyl ether to afford the title compound (10 g, 93.4%) as a pale yellow solid. LCMS (ES+) 186.95 (M+H)+, RT 1.31 minutes (method 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. 171887-03-9, N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UCB PHARMA S.A.; KATHOLIEKE UNIVERSITEIT LEUVEN, K.U.LEUVEN R&D; BROOKINGS, Daniel Christopher; FORD, Daniel James; FRANKLIN, Richard Jeremy; GHAWALKAR, Anant Ramrao; KULISA, Claire Louise; NEUSS, Judi Charlotte; REUBERSON, James Thomas; WO2013/68458; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 137281-39-1, 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. 137281-39-1, name is 4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid. A new synthetic method of this compound is introduced below.

4. 4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic acid (60 g 0.2 mol) Add to a 500ml four-neck bottle,Add 200ml of DMF and 40.4g of triethylamine to warm up to 30C and stir to dissolve.Trityl chloride (0.3 mol) was added dropwise, and the reaction was kept at 35 C for 1 hour.Evaporate DMF under reduced pressure,Add 200ml of pure water and stir.Adjust the pH to 5-6 with dilute hydrochloric acid, stir the crystallization,Cool down to 0-5C suction filtration,Drying the product 4-[2-(2-tritylamino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic acid (molar yield 96.3%, purity 99.2%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,137281-39-1, 4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid, and friends who are interested can also refer to it.

Reference:
Patent; Lunan Pharmaceutical Group Co., Ltd.; Zang Chao; Xia Mingjun; (11 pag.)CN110305136; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 5909-24-0 ,Some common heterocyclic compound, 5909-24-0, molecular formula is C8H9ClN2O2S, 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.

After dissolving 50.0 g of 4-chloro-5-ethoxycarbonyl-2-methylthiopyrimidine and 59.9 ml of triethylamine into 430 ml of ethyl acetate, respectively, the mixture was cooled to 0 C, 44.7g of 3-chloro-4-methoxybenzylamine was added in portions, the reaction was carried out at 0-5 C for 30min and the reaction was continued at 20-30 C for 0.5-1h. The reaction was concentrated under reduced pressure, and then added ethyl acetate and citric acid solution 400ml each wash 2 times, the organic phase was washed with water and saturated brine each time, dried, filtered and concentrated under reduced pressure to give the crude 73.0g. Finally, with anhydrous ethanol at 55 ~ 60 C dissolved crude, stirring crystallization 12-18h, filtered and dried to give the product 42.3g.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5909-24-0, its application will become more common.

Reference:
Patent; Guangzhou Langsheng Pharmaceutical Co., Ltd.; Chen Yuhua; Lu Pingping; Mo Enqing; Zuo Lian; Lu Zhijun; Peng Guizi; Yuan Yongling; (14 pag.)CN104059025; (2017); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 2915-16-4, name is 2-Chloro-4,6-diphenylpyrimidine. A new synthetic method of this compound is introduced below., HPLC of Formula: C16H11ClN2

A mixture of 2-chloro-4,6-diphenylpyrimidine, 250mg (0.94 mmol), 4- (5-CHLORO-LH-INDOL-3-YL)-4-OXO-BUTYRIC acid 2- trimethylsilanyl-ethyl ester, 380mg (1.03 mmol), K2CO3 260mg (1.87 mmol), and N, N-dimethylaminopyridine, llmg (0.09 mmol) in 20mL DMSO was heated to 80 C for 6h. The mixture was cooled to room temperature and diluted with LOOML of EtOAc. The mixture was washed with sat. aq. LiCl (3XLOOML), water (3XLOOML), sat. aq. NACL (LXLOOML), and dried (MGS04). After the solution was concentrated, the residue was purified via column chromatography (eluted with 10% EtOAc-heptane) to afford the desired product in 0.47g (88%) as a pale yellow SOLID. 1H NMR (DMSO-d6) : 6 9.39 (s, 1H), 8.87 (d, 1H, J = 9.7Hz), 8.56 (s, 1H), 8.51-8. 48 (m, 3H), 8.26 (d, 1H, J = 2.7Hz), 7.64-7. 62 (m, 5H), 7.52 (dd, 1H, 9.7, 2.7Hz), 4.10 (dd, 2H, J = 9.0, 9. OHZ), 3.40 (t, 2H, J = 7.2Hz), 2.67 (t, 2H, J = 7.2Hz), 0.94 (dd, 2H, J = 9.0, 9. 0HZ), 0.00 (s, 9H).

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, 2915-16-4, 2-Chloro-4,6-diphenylpyrimidine.

Reference:
Patent; THE INSTITUTES FOR PHARMACEUTICAL DISCOVERY, LLC; WO2004/99159; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 10457-14-4, 2,4-Bis((trimethylsilyl)oxy)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, 10457-14-4, blongs to pyrimidines compound. Product Details of 10457-14-4

Compound 3a (prepared according to Tetrahedron Letters, 1993, 8579; 16.4 g, 30 mmol) was dissolved in 75 mL of each DCE and ACN in a 400 mL high pressure vessel. To this was added Bis(TMS)uracil (12 g, 47 mmol) as solid and lastly Ag(OTf) (11 g, 43 mmol) was added. The reaction was sealed and heated at 135 C. for 90 minutes. The reaction mixture was then cooled to rt and precipitous AgBr filtered off. Solvents were then removed under vacuum and resulting residue was redissolved in EtOAc and aq. NaHCO3. Resulting mixture was extracted 3× with EtOAc, then organics were washed with water (1×), aq. sodium bicarbonate (2×), water (2×) and brine (1×) before drying over sodium sulfate. The solution was then filtered and evaporated to dryness. The residue was purified by silica gel chromatography with Hex:EtOAc to afford 3b (12.8 g; yield 74%). MS [M+H+]=581.9. 1H NMR: (400 MHz, CD3OD) delta 8.15 (1H, d, J=8.4 Hz), 5.68 (1H, d, J=8.4 Hz), 4.52 (1H, d), 4.26 (1H, m), 4.06 (1H, dd), 3.97 (1H, dd, J=12.8, 2.0 Hz), 3.73 (1H, dd, J=12.8, 2.0 Hz). MS [M-H+]=268.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10457-14-4, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; US2012/263678; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 26830-94-4, 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 26830-94-4, name is 2,6-Dichloropyrimidine-4-carbonyl chloride. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2,6-dichloropyrimidine-4-carbonyl chloride (26.13 g, 123.6 mmol) in Et2O (500 mL) was added a mixture of 0.5M ammonia in dioxane (250 mL, 125 mmol) and iPr2NEt (22 mL, 126 mmol) dropwise over approximately 50 minutes. After stirring overnight the reaction was concentrated in vacuo to a residue and chromatographed over silica gel with 10-50% EtOAc in hexanes. The product fractions were evaporated in vacuo, and the resulting solid residue triturated with 10 mL 10% EtOAc/hexanes and filtered to give 2,6-dichloropyrimidine-4-carboxamide as an orange crystalline solid (9.743 g, 50.74 mmol, 41 % yield). LC/MS: m/z= 192.2[ +H]+, 1H NMR (400 MHz, DMSO-d6): 8.40 (1 H, br s), 8.16 (1 H, br s), 8.10 (1 H, s).

According to the analysis of related databases, 26830-94-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PURDUE PHARMA L.P.; LOCKMAN, Jeffrey; NI, Chiyou; PARK, Jae Hyun; PARK, Minnie; SHAO, Bin; TAFESSE, Laykea; YAO, Jiangchao; YOUNGMAN, Mark, A.; WO2014/135955; (2014); 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.74901-69-2, name is 2,4-Dichloro-6,7-dihydrothieno[3,2-d]pyrimidine, molecular formula is C6H4Cl2N2S, molecular weight is 207.08, as common compound, the synthetic route is as follows.name: 2,4-Dichloro-6,7-dihydrothieno[3,2-d]pyrimidine

6.1 (2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl)-(tetrahydropyran-4-yl)-amine (III-6) 0.68 g (II) are placed in 6 ml dioxane, then first 1.72 ml diisopropylethylamine are added, followed by 0.6 g of 4-aminotetrahydropyran. The reaction mixture is heated to 130 C. until there is no further reaction then cooled and evaporated down. The product is treated with water in the ultrasound bath, then suction filtered and dried. 0.66 g (III-6) are obtained in the form of a solid. Analytical HPLC-MS (method C): RT=1.08 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,74901-69-2, 2,4-Dichloro-6,7-dihydrothieno[3,2-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/35143; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 26032-72-4, name is 2,4-Dichloro-6-phenylpyrimidine, molecular formula is C10H6Cl2N2, 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. Quality Control of 2,4-Dichloro-6-phenylpyrimidine

In argon atmosphere, intermediate G (2.04g, 5.0 mmol), intermediate E (0.56g, 2.5 mmol), tris(dibenzilideneacetone)dipalladium (0.092g, 0.10 mmol), tri-t-butylphosphonium tetrafluoro borate (0.116g, 0.40 mmol), t-butoxy sodium (0.67g, 7.0 mmol) and dehydrated toluene (25 mL) were sequentially added. The resulting mixture was heated under reflux for 8 hours. After the reaction mixture was cooled to room temperature, the organic phase was separated, and the organic solvent was distilled off under reduced pressure. The residue obtained was purified by means of silica-gel chromatography to obtain H-3 (1.95g, yield: 81%). HPLC: Purity 99.9% FD-MS: calcd for C70H44N6=969, found m/z=969 (M+, 100)

With the rapid development of chemical substances, we look forward to future research findings about 26032-72-4.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; IKEDA, Kiyoshi; ITO, Mitsunori; EP2662368; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 129872-81-7, 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. 129872-81-7, name is 2,4-Dichloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidine. A new synthetic method of this compound is introduced below.

4-(2-Chloro-5-methyl-5H-pyrrolo[3,2-Patent; VALEANT RESEARCH & DEVELOPMENT; WO2006/122003; (2006); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia