Day: September 6, 2021

Synthetic Route of 18593-44-7, 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 18593-44-7, name is 5,6-Dimethylthieno[2,3-d]pyrimidin-4(3H)-one. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A solution of 4-hydroxy-5,6,7,8-tetrahydrobenzothieno[2,3-d] pyrimidine (1.0 g, 4.85 mmol) in phosphorous oxychloride (10 mL) was heated to 90 oC for 3 h. Excess phosphorus oxychloride was removed in vacuo and then ice-water (40 mL) was added. The solution was then basified by addition of solid sodium hydrogen carbonate in small portions. The precipitate that resulted was filtered off, washing with water to obtain an off-white solid (1.0 g, 92%)

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 18593-44-7, 5,6-Dimethylthieno[2,3-d]pyrimidin-4(3H)-one.

Reference:
Article; Sleebs, Brad E.; Nikolakopoulos, George; Street, Ian P.; Falk, Hendrik; Baell, Jonathan B.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 19; (2011); p. 5992 – 5994;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1193-24-4, 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 1193-24-4, name is 4,6-Dihydroxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A kind of the improved 4, 6 – dichloro pyrimidine production process, characterized in that the production process comprises the following steps: (1) to the reaction kettle top feed port input 1 parts by weight of 4, 6 – dihydroxy pyrimidine and 3 parts by weight of chloroform, opening the stirrer stirring, continue adding 0.5 parts by weight of pyridine catalyst, and then open the jacket steam make the reaction kettle temperature to rise to 50 C, from the reactor into the bottom of the 1 parts by weight of phosgene to the phosgenation reaction, after the reaction is complete, to inject the nitrogen in the reactor catches up with was mad, at the same time the exhaust gas by the pipe into the absorption tower; (2) to be step 1 the product in the transfer to the rectifying tower, control rectification temperature is 65 C, collecting chloroform fraction, to be its after cooling to room temperature, the filling storage recycling; (3) collecting the step 2 in the remaining product, transferred to ice in the ice solution, slowly dropping concentration is 10% hydrochloric acid to adjust the pH of the solution to 5, standing the solution is layered, then methyl tert-butyl ether to the organic phase extraction, extraction 3 – 4 times, saturated copper sulfate solution for washing, until the copper sulfate solution is not color-changing, collecting pyridine circulation use; (4) the step 3 in the remaining product to filter, washing, and drying to obtain the target product 4, 6 – dichloro pyrimidine.The beneficial effects of the present invention: 1) using phosgene to replace the traditional process of phosphorus oxychloride, to avoid the emergence of phosphorus-containing by-product, the protection of the environment; 2) by adding pyridine catalyst, can accelerate the reaction of generating; 3) traditional use phosphorus oxychloride with 4, 6 – dihydroxy pyrimidine chloride obtained when the 4, 6 – two chlorine pyrimidine, easy to produce 3 different by-product, so that the trouble in processing after, and the yield of target product is not high, in the reaction of the present invention less by-products, and the yield of 4, 6 – dichloro pyrimidine higher; 4) by adjusting the solution pH, methyl tert-butyl ether extraction, and sulfuric acid copper and washing the collecting various pyridine, avoiding the traditional rectification, and steaming and method and the like caused by the leakage of pyridine, ensures the safety of the operators.

According to the analysis of related databases, 1193-24-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Anhui Guangxin Agrochemical Co., Ltd; Huang, Jinxiang; Guo, Xuejun; wu, Jianping; hu, minghong; tang, Xiude; cheng, Weijia; li, Hongwei; Xu, Xiaobing; Yang, Zhiwei; Gao, yanbing; (4 pag.)CN106187913; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 591-55-9, 5-Aminopyrimidine, 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, name: 5-Aminopyrimidine, blongs to pyrimidines compound. name: 5-Aminopyrimidine

Example 11 Preparation of Compound Nos. 7, 7a and 7b To a solution of 1-(4-(3-cyclopropyl-1H-pyrazol-5-ylamino)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)pyrrolidine-2-carboxylic acid (300 mg, 0.847 mmol) in DMF (4 mL) was added pyrimidin-5-amine (201 mg, 2.11 mmol), HATU (386 mg, 1.016 mmol) and DIPEA (0.24 mL, 1.4 mmol). The reaction mixture was allowed to stir at RT for 16 h. The reaction mixture was diluted with water (40 mL) and extracted with EtOAc (2*25 mL). The organic layer was washed with water (8*30 mL) and dried over anhydrous sodium sulfate. Removal of EtOAc under reduced pressure gave a crude product that was purified by reverse phase HPLC to afford 11 mg of 1-(4-(3-cyclopropyl-1H-pyrazol-5-ylamino)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)-N-(pyrimidin-5-yl)pyrrolidine-2-carboxamide as free base. 1H NMR (400 MHz, CD3OD, formate salt) delta (ppm): 0.58-0.67 (m, 2H), 0.80-0.94 (m, 2H), 1.70-1.78 (m, 1H), 2.09-2.21 (m, 4H), 2.22-2.42 (m, 2H), 2.78-2.81 (m, 2H), 2.82-2.95 (m, 2H), 3.60-2.70 (m, 1H), 3.78-3.88 (m, 1H), 4.78 (dd, 1H), 6.08 (s, 1H), 8.84 (s, 1H), 8.89 (s, 2H). Separation by chiral HPLC provided enantiomers 7a and 7b.

The synthetic route of 591-55-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; CHAKRAVARTY, Sarvajit; RAI, Roopa; GREEN, Michael John; US2014/179668; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 374930-88-8, Adding some certain compound to certain chemical reactions, such as: 374930-88-8, name is tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate,molecular formula is C13H19BrN4O2, 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 374930-88-8.

Synthesis of tert-butyl 4-(5-acetylpyrimidin-2-yl)piperazine-1-carboxylate To a mixture of tert-butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate (5.0 g, 14.6 mmol), palladium diacetate (240 mg, 1.46 mmol) and triphenylphosphine (376 mg, 2.92 mmol) in dioxane (100 mL) was added tributyl(1-ethoxyvinyl)stannane (5.3 mL, 16.1 mL) under N2, and the reaction mixture was stirred at 80 C. overnight. The reaction was cooled to RT and diluted with THF (100 mL), followed by the addition of 2 N HCl (100 mL). The mixture was stirred at RT for 30 mins, and LCMS showed the reaction was completed. The reaction mixture was diluted with ethyl acetate (200 mL). The organic phase was separated, washed with water (3*100 mL), dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography to afford the title compound (3.0 g, 67%). MS (ES+) C15H22N4O3 requires: 306, found: 251 [M-56+H]+.

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. 374930-88-8, tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; Hodous, Brian L.; Kim, Joseph L.; Miduturu, Chandrasekhar V.; Wilson, Douglas; Zhang, Yulian; US2015/111857; (2015); A1;,
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. 22276-95-5, name is 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below., Recommanded Product: 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

To a solution of 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (E-2) (2.33 g, 10.0 mmol, 1.0 eq) in anhydrous THF (100 mL) at -78 C under argon, n-BuLi solution (2.5 M in THF, 8.8 mL, 22.0 mmol, 2.2 eq) is added dropwise (over 10 min). The resulting mixture is stirred at -78 C for lh and then DMF (2.0 g, 11.0 mmol, 1.1 eq) is added dropwise (over 10 min). The mixture is stirred at -78 C for an additional 30 min and then stirred at RT overnight. The reaction mixture is quenched with H20 (50 mL) and then concentrated in vacuo. The residue is triturated with saturated aqueous NH4C1 solution. The solid is collected by filtration, rinsed with ethyl acetate, and dried in vacuo to afford the product, 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde (E-3).

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, 22276-95-5, 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; INTELLIKINE, INC.; INFINITY PHARMACEUTICALS, INC.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; CASTRO, Alfredo, C.; EVANS, Catherine, A.; WO2011/146882; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 111196-81-7, 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 111196-81-7, name is 2-Chloro-5-ethylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Step-4: Synthesis of 5-ethyl-2-(5,6-dihydro-4-(4-(4-(methyl sulfonyl)phenyl)-1,2,5-thiadiazol-3-yl)pyridin-1(2H)-yl)pyrimidine To a stirred solution of 1,2,3,6-tetrahydro-4-(4-(4-(methylsulfonyl)phenyl)-1,2,5-thiadiazol-3-yl)pyridine hydrochloride (0.04 g, 0.111 mmol) and 2-chloro-5-ethylpyrimidine (0.023 g, 0.166 mmol) in DMF (5 mL) was added DIPEA (0.45 mL, 0.555 mmol) and stirred at 100 C. for 16 h. Reaction was monitored by TLC. On completion reaction mass was quenched with water, extracted with ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulphate evaporated under reduced pressure obtained crude which was purified by silica gel (100-200 Mesh) column chromatography, eluent 25% EtOAc/Hexane to afford 5-ethyl-2-(5, 6-dihydro-4-(4-(4-(methylsulfonyl)phenyl)-1,2,5-thiadiazol-3-yl)pyridin-1(2H)-yl)pyrimidine (0.024 g, 51.06%) as off white solid. MS: 428.11 [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 111196-81-7, 2-Chloro-5-ethylpyrimidine.

Reference:
Patent; Mankind Pharma Ltd.; Patil, Rakesh Ishwar; Verma, Jeevan; Kumar, Puneet; Gunjal, Amol Pandurang; Rai, Himanshu; Rai, Santosh Kumar; Kumar, Anil; (106 pag.)US2017/291894; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 4994-86-9, 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. 4994-86-9, name is 4-Chloro-2-methylpyrimidine, molecular formula is C5H5ClN2, 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: Two solutions, one with the aryl halide (0.56 mmol, 1.0equivalent) in THF-H2O (2.5 mL, 3:2 v/v) and one with phenol (0.84mmol, 1.5 equivalent) and NaOH (0.84 mmol, 1.5 equivalent) in THF-H2O(2.5 mL, 3:2 v/v) were prepared and then introduced into Asia microfluidicreactor by Pump A & B.. The mixture was pumped through a preheated 1 mL glassmicrofluidic reactor at a predetermined flow rate to achieve the desiredresidence time. The crude product was collected in a flask and extracted withethyl acetate. The organic phase was combined, dried MgSO4 andconcentrated under reduced pressure. The isolated crude product was purifiedusing a prepacked silica cartridge on a Teledyne CombiFlash Rf 200instrument. Fractions corresponding to the product peak were combined andconcentrated using rotavap. For the synthesis of compound 3e and 3f correspondingsodium alkoxides were used as input for the second pump.

According to the analysis of related databases, 4994-86-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Alam, Mohammad Parvez; Jagodzinska, Barbara; Campagna, Jesus; Spilman, Patricia; John, Varghese; Tetrahedron Letters; vol. 57; 19; (2016); p. 2059 – 2062;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 959070-42-9, 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. 959070-42-9, name is Ethyl 4,6-dichloro-2-(methylthio)pyrimidine-5-carboxylate. A new synthetic method of this compound is introduced below.

To a solution of ethyl 4,6-dichloro-2-(methylthio)pyrimidine-5-carboxylate (47.0 g, 175.94 mmol) in DMF (470 mL) and diisopropylethylamine (100.43 mL, 582.7 mmol) was added ethyl 3-(phenylamino)propanoate (31.0 g, 160.4 mmol). The reaction mixture was heated to 100 C. and stirred for 7 h. Upon completion of the reaction (monitored by TLC), DMF was evaporated under reduced pressure and water (250 mL) was then added. The reaction mixture was extracted using EtOAc (200 mL×3). The combined organic layer was washed with water (500 mL×2), brine (500 mL), dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to give a residue. The residue was purified by silica gel column chromatography (using 0-20% Ethyl acetate in hexane) to afford ethyl 4-chloro-6-((3-ethoxy-3-oxopropyl)(phenyl)amino)-2-(methylthio)pyrimidine-5-carboxylate (55 g, 80.8% yield). 1H NMR (400 MHz, CDCl3): delta 7.38 (t, J=8.0 Hz, 2H), 7.31 (d, J=7.6 Hz, 1H), 7.18 (d, J=7/2 Hz, 2H), 4.26 (t, J=7.6 Hz, 2H), 4.05 (q, J=7.2 Hz, 2H), 3.47 (q, J=7.2 Hz, 2H), 2.68 (t, J=7.6 Hz, 2H), 2.54 (s, 3H), 1.19 (t, J=7.2 Hz, 3H), 1.08 (t, J=7.2 Hz, 3H). LCMS [M+H]; 424

At the same time, in my other blogs, there are other synthetic methods of this type of compound,959070-42-9, Ethyl 4,6-dichloro-2-(methylthio)pyrimidine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ArQule, Inc.; US2010/249110; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 3680-69-1, 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.3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H4ClN3, molecular weight is 153.5691, as common compound, the synthetic route is as follows.

N,N-Dimethylformamide (DMF) (47mL) was added to a mixture of 56 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (4.60g, 29.8mmol) and 57 N-iodosuccinimide (6.82g, 30.3mmol) under a nitrogen atmosphere. The solution was stirred at 22C for 2.5h before the mixture was poured into ice water (150mL). The precipitate was filtered, washed with water and n-pentane and dried to give 7.05g (25.2mmol, 85%) of 12 1 as a pale brown powder; mp. 187-188C (dec.) (lit [39]. 196-199C), Rf=0.16 (n-pentane/EtOAc, 10/1). 1H NMR (400MHz, DMSO-d6): 12.94 (br s, 1H), 8.59 (s, 1H), 7.94 (d, J=2.5, 1H). The spectroscopic data corresponded well with that reported previously [39].

The chemical industry reduces the impact on the environment during synthesis 3680-69-1, I believe this compound will play a more active role in future production and life.

Reference:
Article; Reiers°lmoen, Ann Christin; Han, Jin; Sundby, Eirik; Hoff, Bard Helge; European Journal of Medicinal Chemistry; vol. 155; (2018); p. 562 – 578;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 3934-20-1, 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.3934-20-1, name is 2,4-Dichloropyrimidine, molecular formula is C4H2Cl2N2, molecular weight is 148.9781, as common compound, the synthetic route is as follows.

A stirred solution of 2,4-dichloropyrimidine (5.00g, 36.5mmol) and diisopropylethylamine (14.0ml, 80.4mmol) in EtOH (60ml) at 0C was treated with morpholine (3.18ml, 36.5mmol) and allowed to warm to ambient temperature overnight. The solution was poured into brine and extracted with DCM. The organics were dried (MgS04), filtered and evaporated. The residue was purified by column chromatography (Si02, 5% EtOH in DCM) to afford the title compound IIIc as a white solid (1.3g, 36%). XH NMR (300 MHz, DMSO-d6) delta 8.10 (d, J = 6.2 Hz, 1H), 6.83 (d, J = 6.2 Hz, 1H), 3.72 – 3.49 (m, 8H).

The chemical industry reduces the impact on the environment during synthesis 3934-20-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; AB SCIENCE; BENJAHAD, Abdellah; MARTIN, Jason; SCHALON, Claire; PEZ, Didier; CHEVENIER, Emmanuel; SANDRINELLI, Franck; PICOUL, Willy; MOUSSY, Alain; WO2015/144614; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia