Tag: M.W:100-200

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. 42754-96-1, name is 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine

To a solution of cyclopropylmethanol (1.908 g, 26.5 mmol) in THF (200mL) was addedsodium hydride (3.17 g, 79 mmol) in an ice bath. After stirred for 30 mm, 4,6-dichloro-1H- pyrazolo[3,4-d]pyrimidine (5 g, 26.5 mmol). The reaction mixture was gradually allowed to room temperature and stirred overnight. Then the mixture was diluted with water (80 mL), concentrated to remove solvent and diluted with ethyl acetate (220 mL). The organic layerwas washed with water (80 mLx 2), dried over Na2SO4, filtered and concentrated. The crude(5 g, 84% yield) was directly used into next step.LCMS: 225[M+H]. tR2.9l8 (LCMS condition 1)

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, 42754-96-1, 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; DING, Xiao; LIU, Qian; LONG, Kai; SANG, Yingxia; STASI, Luigi Piero; WAN, Zehong; XU, Qiongfeng; EDGE, Colin Michael; WO2015/113451; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 10320-42-0, 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.10320-42-0, name is 2-Chloro-5-nitropyrimidine, molecular formula is C4H2ClN3O2, molecular weight is 159.5306, as common compound, the synthetic route is as follows.

Example 41Synthesis of N-(2-chloro-5-pyrimidinyl)-4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-amineThe compound was synthesized according to Method A.A suspension of 3.5 g (63 mmol) of iron dust in 10 mL of 1.5% aq. AcOH and 35 mL of 65% EtOH was heated to 80 C., and 1.005 g (6.28 mmol) of 2-chloro-5-nitropyrimidine was added. The reaction mixture was then heated at 90 C. for 1 hr. After cooling to room temperature, the reaction mixture was neutralized with aq. NH3, filtered through celite, and concentrated in vacuo. The residue was extracted with EtOAc (¡Á4), and the organic layer was washed with brine, dried (Na2SO4), and concentrated. Chromatography on silica, eluting with hexanes/EtOAc (6:4), gave 0.49 g (60% yield) of 5-amino-2-chloropyrimidine as a yellow powder: 1H NMR (DMSO-d6) delta8.03 (s, 2H); LCMS (APCI+) m/z: 130 (MH+, 100%).A mixture of 0.28 g (0.71 mmol) of 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazole, 0.076 g (0.56 mmol) of the above amine, 0.026 g (0.04 mmol) of BINAP, 0.01 g (0.04 mmol) of Pd(OAc)2, and 0.266 g (0.82 mmol) of Cs2CO3 in 1,4-dioxane (4 mL) was heated at 100 C. for 3 hrs under nitrogen. The mixture was cooled to room temperature, sat. NaHCO3 solution was added, and the resulting mixture was extracted with EtOAc (¡Á4). The organic layer was washed with brine, dried (Na2SO4), and concentrated. Chromatography on silica, eluting with CH2Cl2/EtOAc (6:1), gave 0.10 g (36% yield) of N-(2-chloro-5-pyrimidinyl)-4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-amine, as a white powder: mp 295 C. (decomp.); 1H NMR (DMSO-d6) delta10.43 (s, 1H), 9.08 (s, 2H), 8.09-7.69 (m, 2H), 7.42 (t, J=8.0 Hz, 1H), 6.98 (d, J=7.6 Hz, 1H), 3.98 (s, 3H), 3.83 (s, 4H), 3.75-3.73 (m, 4H); Anal. Calcd. for C20H18ClF2N9O2: C, 49.0; H, 3.7; N, 25.7. Found: C, 49.2; H, 3.9; N, 25.45%.

Statistics shows that 10320-42-0 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-nitropyrimidine.

Reference:
Patent; Pathway Therapeutics Limited; US2011/9405; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 21236-97-5, 6-Amino-3-methylpyrimidine-2,4(1H,3H)-dione, 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, Recommanded Product: 21236-97-5, blongs to pyrimidines compound. Recommanded Product: 21236-97-5

Representative procedure for the synthesis of dihydropyrido[2,3-d]pyrimidines 4: N,N-Dimethyl-6-aminouracil 1a (0.310 g, 2 mmol benzaldehyde 2a (0.212 g, 2 mmol), 3-cyanoacetyl indole 3 (0.368 g, 2 mmol) were taken in a round bottom flask containing ethanol (10 mL). To this was added InCl3 (5 mol %) and the reaction mixture was refluxed for 6 h. After completion of the reaction (monitored by TLC), the reaction mixture was cooled and filtered. The solid product obtained was washed with water and ethanol, and finally recrystallized from ethanol. The structure of the compound was ascertained as 4a from the spectroscopic data and elemental analysis. Yield = 0.670 g (82%) Compound 4a: Similarly compounds 4b-q were synthesized and characterized.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,21236-97-5, 6-Amino-3-methylpyrimidine-2,4(1H,3H)-dione, and friends who are interested can also refer to it.

Reference:
Article; Seetham Naidu; Borah, Pallabi; Bhuyan, Pulak J.; Tetrahedron Letters; vol. 53; 31; (2012); p. 4015 – 4017;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 5399-92-8, 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. 5399-92-8, name is 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C5H3ClN4, 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.

The starting material B-Cl(1a-n) (12.94 mmol) was weighed and dissolved in DMF (10 mL).DIEA (51.76mmol),1-Boc piperazine (15.53 mmol) was added to the reaction flask and reacted at 90 C for 4 h.The reaction was completely detected by TLC, and the reaction solution was poured into 10 times of ice water.A large amount of white solid was precipitated, filtered, and the cake was washed with water (20 ml ¡Á 3) and dried.Intermediate 2 was obtained. In the above preparation, la is 4-chloro-1H-pyrazolo[3,4-d]pyrimidine, which gives 2a as a white solid, yield 89%

According to the analysis of related databases, 5399-92-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shandong University; Zhao Guisen; Guo Kaiwen; Dong Junze; Yang Dezhi; Jing Yongkui; (25 pag.)CN108822110; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 10320-42-0, 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. 10320-42-0, name is 2-Chloro-5-nitropyrimidine, molecular formula is C4H2ClN3O2, 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.

2-chloro-5-nitropyrimidine (1 g, 6.27 mmol) was mixed with ethylene glycol (8ml, 143 mmol) and DIEA (3.28 ml, 18.81 mmol) was added. The mixture was stirred at80 ¡ãC for 20 minutes and was then poured into 30 mL of ice water. 40 mL of EtOAc was added to the mixture followed by 20 mL of iN aq. HC1. EtOAc (30 mL x 3) was used to extracted aq. Layer. The combined organic layer was washed with brine, dried with sodium sulfate, filtered and concentrated to give Intermediate I-57A in quantitative yieldas a yellow oil. The product was brought forward without further purification. ?H NMR(400MHz, CHLOROFORM-d) oe 9.33 (s, 2H), 4.73-4.51 (m, 2H), 4.08-3.96 (m, 2H), 2.41 (br. s., 1H).

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 10320-42-0, 2-Chloro-5-nitropyrimidine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; HALPERN, Oz Scott; JIANG, Wen; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (545 pag.)WO2018/13776; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 5750-76-5 ,Some common heterocyclic compound, 5750-76-5, molecular formula is C4HCl3N2, 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-(isopropylsulfonyl)aniline (3g, 14mmol), add DMF 30ml. Under ice-water bath add batchwise sodium hydride (0.73g, 30mmol), Addition is completed. Room temperature stirring 30min. Add 2,4,5-trichloropyrimidine (3.31g, 18mmol). Stirring at the room temperature 16h. ice water quenching of the reaction, ethyl acetate (30 ml * 3), the combined organic layer, water washing, salt is washed with water, concentrated to dryness to obtain white solid 1.7g, yield 37%, in order to 2 – (isopropyl sulfonyl) aniline calculation.

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. 5750-76-5, 2,4,5-Trichloropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nanjing Qike Pharmaceutical Co., Ltd.; Wu Xueping; Han Dong; Shi Zhuyong; (8 pag.)CN104356112; (2017); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 851984-15-1, 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 851984-15-1, name is 6-Chloro-5-fluoropyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of (3S,4S)-3-aminopiperidin-4-ol 6 (9.4 g, 81.0 mmol, 1.0 equiv) in n-BuOH (100 ml) was added 6-chloro-5-fluoro-pyrimidin-4-ylamine (11.3 g, 76.9 mmol, 0.95 equiv) and the mixture was heated to 120 C overnight. The solid crystallized upon cooling to 20 C. After stirred for 2 h, the mixture was filtered and the solids were washed with MTBE (100 ml), dry under vacuum at 50 C (-0.08 Mpa) for -4-5 hours to afford 17 as a gray solid (17 g, 79.8%). 1H NMR (DMSO-d6, 400 MHz) delta: 1.40-1.45 (m, 1H), 1.93 (m, 1H), 2.60-2.69 (m, 2H), 2.90 (t, J = 12.0 Hz, 1H), 3.41-3.47 (m, 1H), 3.93-4.01 (m, 2H), 7.59 (s, 1H). MS: 227; MS Found: 228 ([M+1]+

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 851984-15-1, 6-Chloro-5-fluoropyrimidin-4-amine.

Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian, T.; CAI, Xiongwei; CHAN, Timothy R.; CONLON, Patrick; HUMORA, Michael; JENKINS, Tracy J.; MACPHEE, J. Michael; SHI, Xianglin; MILLER, Ross A.; THOMPSON, Andrew; WO2013/185082; (2013); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 105806-13-1 , The common heterocyclic compound, 105806-13-1, name is 4,6-Dichloro-5-fluoro-2-methylpyrimidine, molecular formula is C5H3Cl2FN2, 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.

Part A: 5-Fluoro-6-hydrazino-N,2-dimethyl-N-(4-pyridinylmethyl)-4-pyrimidinamine. 4,6-Dichloro-5-fluoro-2-methylpyrimidine (0.18 g, 0.99 mmol) was dissolved in DMSO (1 ml_). To this solution was added triethylamine (0.15 ml_, 1.08 mmol), followed by commercially available N-methyl-1-(4-pyridinyl)methanamine (0.122 g, 1.0 mmol). The reaction was left to stir for 3 hours. Then hydrazine monohydrate was added, and the resulting reaction mixture was stirred overnight at room temperature. The reaction mixture was heated to 6O0C for 90 minutes. After cooling, the reaction mixture was purified by RP-HPLC to provide 5-fluoro-6-hydrazino-N,2-dimethyl-N-(4-pyridinylmethyl)- 4-pyrimidinamine (0.130 g, 49%). LCMS: (M+H)+ = 263.0.

The synthetic route of 105806-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/61879; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 60025-09-4, 4-Amino-6-chloropyrimidine-5-carbonitrile, 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, Recommanded Product: 4-Amino-6-chloropyrimidine-5-carbonitrile, blongs to pyrimidines compound. Recommanded Product: 4-Amino-6-chloropyrimidine-5-carbonitrile

24.89 kg of tetrahydrofuran was added to a 100 L reaction kettle, and stirring was started, followed by the addition of 2.84 kg of (S)-3-(1-aminoethyl)-8-chloro-2-phenylquinolin-4(1H)-one and 1.34. Kg 4-amino-5-cyano-6-chloropyrimidine, heated to 65 ¡À 5 C, then add 4.22 kg of cesium carbonate, continue to reflux for 1 to 1.5 hours, HPLC to monitor the reaction to the end; 7.10 kg of acetone was washed, the solvent was removed from the filtrate, and 20 kg of purified water was added thereto for stirring for 1 to 2 hours, and the mixture was centrifuged, and purified water was washed twice. The obtained solid was air-dried at 70 ¡À 5 C for 10 hours or more to obtain 3.55 kg of the title compound.3.55 kg of the above crude product was added to 43.34 kg of acetone at room temperature, stirred until it was dissolved, filtered, and the filtrate was added to a 100 L reaction vessel, heated to reflux, and some acetone was distilled off until the residue in the kettle was slightly turbid, and the mixture was slowly added dropwise. Kg of methanol, after the completion of the addition, naturally reduce to room temperature, then cool to 5 ¡À 5 C, heat crystallization for more than 1 hour, filtration, filter cake with a mixture of 0.78 kg weight ratio of acetone / methanol = 1/2, the resulting The solid was vacuum dried at 60 ¡À 5 C for more than 12 hours to obtain 2.23 kg of (S)-4-amino-6-((1-(8-chloro-4-oxo-2-phenyl-1,4-di) Hydroquinolin-3-yl)ethyl)amino)pyrimidine-5-cyano, yield 62.0%.

The synthetic route of 60025-09-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Shenghe Pharmaceutical Co., Ltd.; Zhao Liwen; Sha Xiangyang; Ye Shichun; Ding Zhaobing; Chen Cheng; Li Linyi; (19 pag.)CN109516975; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 4318-56-3, 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 4318-56-3, name is 6-Chloro-3-methylpyrimidine-2,4(1H,3H)-dione. This compound has unique chemical properties. The synthetic route is as follows.

Step 1 : 6-Chloro-3-methylpyrimidine-2,4 (l/7,3/7)-dione (43 g, 267 mmol), (1192) K2C03 (92.1 g, 667 mmol) and PMB-C1 (1.4 g, 28.0 mmol) were taken up in DMF (500 mL). The reaction mixture was stirred at 50 C for 16 hours. The mixture was partitioned between H20 (1000 mL) and EtOAc (1500 mL) and the aqueous phase was extracted with EtOAc (800 mL x 2). The combined organics were washed with brine (500 mL x 2), dried over anhydrous Na2S04, filtered, and concentrated under reduced pressure to give a residue.Trituration with petroleum ether/EtOAc (10 : 1) resulted in the formation of a precipitate which was collected by filtration, washed with petroleum ether/EtOAc (10 : l, 100 mL), and dried to give 6-chloro-l-(4-methoxybenzyl)-3-methylpyrimidine-2, 4(1/7, 3/7)-dione (50.0 g, 66.7% yield) as a white solid.

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 4318-56-3, 6-Chloro-3-methylpyrimidine-2,4(1H,3H)-dione.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; WALTERS, W., Patrick; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; TAYLOR, Alexander, M.; PIERCE, Levi Charles, Thomas; MURCKO, Mark, Andrew; GIORDANETTO, Fabrizio; GREISMAN, Jack, Benjamin; MARAGAKIS, Paul; BHAT, Sathesh; KONZE, Kyle; DAHLGREN, Markus, Kristofer; THERRIEN, Eric; (0 pag.)WO2019/165073; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia