Day: March 8, 2021

Reference of 61727-33-1, 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. 61727-33-1, name is 5-Chloro-2-(methylthio)pyrimidine-4-carboxylic acid, molecular formula is C6H5ClN2O2S, 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.

Preparation Example 2: Preparation of 5-chloro-2-methanesulfonyl- pyrimidine-4-carboxylic acid methyl ester; Step 1) Preparation of 5-chloro-2-methylsulfanyl-pyrimidine-4-carboxylic acid methyl ester; 5-chloro-2-methylsulfanyl-pyrimidine-4-carboxylic acid (2.04 g, 10 mmol) was added to methanol, and 10 m? of thionyl chloride was slowly added thereto, followed by stirring the mixture for 5 hours. The resulting mixture was concentrated under a reduced pressure to remove the solvent, and sequentially washed with sodium bicarbonate solution and salt solution. The resulting residue was subjected to silica gel column chromatography (eluent: n- hexane/ethyl acetate=5:l) to obtain the title compound (2.1 g; yield: 95 %).

According to the analysis of related databases, 61727-33-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CRYSTALGENOMICS, INC.; WO2007/73117; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 591-55-9, 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 591-55-9, name is 5-Aminopyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 368 mg (1 equiv) of tert-butyl 2-(5-bromo-3-carbamoyl-1H-indazol-1-yl)acetate (112), pyrimidin-5-amine (95 mg, 1 equiv), and cesium carbonate (650 mg, 2 equiv) in DMF (20 mL) was purged with argon in a pressure vessel for 5 min, then tris(dibenzylideneacetone) dipalladium(O) (0.01 equiv) and 4,5-bis(diphenylphosphino)-9,9- dimethylxanthene (0.01 equiv) were added under argon. The pressure vessel was sealed and heated at 100 C for 24 h. The reaction mixture was then cooled to rt and the solvent was removed under reduced pressure. The remaining residue was purified by flash column chromatography (eluted with DCM/CH3OH) to give tert-butyl 2-(3-carbamoyl-5-(pyrimidin-5-ylamino)-1H-indazol-1-yl) acetate (113).

According to the analysis of related databases, 591-55-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (319 pag.)WO2017/35351; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1193-24-4, 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 1193-24-4 as follows.

Example 1-Synthesis of 4, 6-dichloropyrimidine-5-carbaldehyde 1 This compound was synthesized similar to a patent. To POCl3 (107.3 mmol, 10 mL) cooled at 0 C. was added DMF (41.3 mmol, 3.2 mL) dropwise, and the mixture was stirred for 1 h. Then, 4, 6-dihydroxylpyrimidine (22.3 mmol, 2.50 g) was added, stirred for 30 minutes and refluxed for 3 h. After removing the volatiles at reduced pressure, it was poured into ice and extracted with ethyl acetate three times (3*200 mL). The combined ethyl acetate extracts were washed with 200 mL saturated NaHCO3, dried with Na2SO4, and concentrated under reduced pressure to afford 2.91 g, 74% of the desired compound as an orange solid. 1H NMR (500 MHz, CDCl3): delta 10.48 (s, 1H), 9.92 (s, 1H). 13C NMR (125 MHz, CDCl3): delta 185.61, 162.69, 159.58, 124.89.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1193-24-4, its application will become more common.

Reference:
Patent; BOARD OF TRUSTEES OF NORTHERN ILLINOIS UNIVERSITY; Hagen, Timothy J.; Blain, Joy M.; Goshu, Gashaw M.; Hartnett, Brian E.; (35 pag.)US2017/355700; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1004-39-3, Adding some certain compound to certain chemical reactions, such as: 1004-39-3, name is 4,6-Diaminopyrimidine-2-thiol,molecular formula is C4H6N4S, 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 1004-39-3.

General procedure: DBU (0.5 mmol, 0.08 g) was added dropwise at room temperature to a magnetically stirred suspension of appropriate thiol 2 (0.5 mmol) in 1 ml of MeCN. The mixture was stirred for 10 min and then appropriate nitrofuroxan 1 (0.5 mmol) was added. The mixture was stirred for 0.5-10 h until initial compound 1 disappeared (TLC monitoring, eluent – CHCl3). Next, H2O (7 ml) was added and the reaction mixture was acidified with 1 n HCl until pH 1. The produced solid was filtered off, washed with water and the MeCN minimal volume (~1 ml), and air-dried. Compounds 3i and 4 were prepared as a mixture. The mixture was treated with 2 ml of DMSO at 60 C for 30 min; the undissolved solid was filtered off, water-washed and air-dried to afford disulfide 4. The filtrate was diluted with water and the solid was filtered off, water-washed and air-dried to afford compound 3i.

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. 1004-39-3, 4,6-Diaminopyrimidine-2-thiol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fershtat, Leonid L.; Epishina, Margarita A.; Kulikov, Alexander S.; Makhova, Nina N.; Mendeleev Communications; vol. 25; 1; (2015); p. 36 – 38;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 18592-13-7, 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. 18592-13-7, name is 6-(Chloromethyl)pyrimidine-2,4(1H,3H)-dione. A new synthetic method of this compound is introduced below.

A mixture of 18 (0.252 g; 0.5 mmol), 6-chloromethyluracil (0.088g ; 0.55 mmol), K2CO3 (0.076 g; 0.55 mmol) and NaI (0.082 g; 0.55 mmol) in acetonitrile (5 ml) was heated at [85C] under argon atmosphere for 4 hours. The mixture was purified by flash chromatography eluting with a gradient of 5-10 % [MEOH/CH2C12] to give Example 11 as a solid. Yield: 63 [%] [‘H] NMR [(CDC13)] : 1.2-1. 4 (m, 4H); 1.6 (s, 6H); 1.4-1. 8 (m, 4H); 2.34 (s, 6H); 2.4-2. 7 (m, 10H); 2.85-2. 95 (m, 2H); 3.3 (s, 2H); 4-4.2 (m, br, 1H); 4.6-4. 8 (m, br, 1H); 5.53 (s, 1H); 6.72 (s, 1H) ; 6.93 (s, 1H); 7.04 (s, 2H); 8.05-8. 2 (m, 2H). MS-ESI: 629 [M+H] [+]

At the same time, in my other blogs, there are other synthetic methods of this type of compound,18592-13-7, 6-(Chloromethyl)pyrimidine-2,4(1H,3H)-dione, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/18480; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 24415-66-5, 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. 24415-66-5, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, molecular formula is C6H5ClN4, 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 preparation method of the compound e10 comprises the steps of: taking about 1 mmol of 7-chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine and about 3 mmol.1-benzyl-1H-indole was added to a 10 mL microwave reaction tube,Further, 2 mL of hexafluoroisopropanol solvent and about 0.1 mmol of bistrifluoromethanesulfonimide catalyst were added, sealed and heated to 100 C with stirring and reacted for about 6 h.Then, the reaction system was monitored by TLC, and after the reaction system was cooled to room temperature, it was separated and purified by column chromatography to obtain pure compound e10.The compound e10 is a yellow solid with a yield of 90%.

According to the analysis of related databases, 24415-66-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhengzhou University; Liu Hongmin; Yu Bin; Zheng Yichao; Yuan Shuo; Shen Dandan; (27 pag.)CN109020976; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 1500-85-2, 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.1500-85-2, name is 7H-Pyrrolo[2,3-d]pyrimidin-4-amine, molecular formula is C6H6N4, molecular weight is 134.14, as common compound, the synthetic route is as follows.

To a solution of 200 mg (1.49 mmol) of 7H-pyrrolo[2,3-d]pyrimidin-4-amine in 4 mL of DMF, 235 muL of dimethylformamide dimethyl acetal were added. The mixture was stirred at room temperature overnight. The solvent was then removed in vacuo and the residue taken up with DCM, washed with brine, dried over anhydrous Na2SO4and evaporated to dryness. The crude was triturated with diisopropylether and filtered, to afford 204 mg (73%) of the title compound. 1H NMR (600 MHz, DMSO-cie) delta ppm 3.10 (s, 3 H) 3.16 (s, 3 H) 6.45 (dd, J=3.39, 1.92 Hz, 1 H) 7.21 (dd, J=3.11 , 2.38 Hz, 1 H) 8.28 (s, 1 H) 8.79 (s, 1 H) 11.60 (br. s., 1 H) HRMS (ESI) calcd for C9HnN5 [M+H]+ 190.1087, found 190.1085.

The chemical industry reduces the impact on the environment during synthesis 1500-85-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; ANGIOLINI, Mauro; BUFFA, Laura; MENICHINCHERI, Maria; MOTTO, Ilaria; POLUCCI, Paolo; TRAQUANDI, Gabriella; ZUCCOTTO, Fabio; WO2014/184069; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 33034-67-2, 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.33034-67-2, name is 2-Chloro-4-(trifluoromethyl)pyrimidine, molecular formula is C5H2ClF3N2, molecular weight is 182.531, as common compound, the synthetic route is as follows.

Step 4: The product of Step 3 (460 mg, 1.720 mmol), 2-chloro-4-(trifluoromethyl)pyrimidine (314 mg, 1.638 mmol), Xantphos (284 mg, 0.492 mmol), palladium (II) acetate (73.6 mg, 0.328 mmol), cesium carbonate (1.068 g, 3.28 mmol) and dioxane (12.3 mL) were heated at 90 ¡ãC for 90 minutes. The reaction mixture was diluted with ethyl acetate, washed with water and dried over Na2S04. Filtration and solvent evaporation gave a residue which was further purified by column chromatography on silica gel, eluting with 40percent ethyl acetate in hexane to afford l-[5-(3- cMoro-5-{[4-(trifluoromemyl)pyrimidin-2-yl^ as a brown solid (390 mg, 55.8percent). NM (500 MHz, CDCI3): 5 8.71 (d, J – 4.7 Hz, 1 H); 7.92(s, 1 H); 7.85 (s, 1 H); 7.78 (s, 1 H); 7.69 (s, 1 H); 7.25 (s, 1 H); 7.13 (d, J= 4.8 Hz, 1 H); 3.81 (s, 1 H); 2.73 (s, 2 H); 2.58-2.47 (m, 2 H); 2.13-1.97 (m, 2 H) MS APCI: [M+H]+ m/z 427.1. rhSYK activity = ++

The chemical industry reduces the impact on the environment during synthesis 33034-67-2, I believe this compound will play a more active role in future production and life.

Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 4983-28-2, 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. 4983-28-2, name is 2-Chloro-5-hydroxypyrimidine. A new synthetic method of this compound is introduced below.

A stirred mixture of 2-chloro-5-pyrimidinol (107) (1.00 g, 7.66 mmol) and chloromethyl ethyl ether (1.75 mL, 18.9 mmol) in anhydrous DMF (2.5 mL) was treated with K2CO3 (2.15 g, 15.6 mmol). After stirring at room temperature for 16 h, the mixture was added to ice/aqueous NaHCO3 (100 mL) and extracted with 50% Et2O/petroleum ether (5¡Á100 mL). The combined extracts were evaporated to dryness and the residue was chromatographed on silica gel. Elution with 0-1% Et2O/petroleum ether firstly gave foreruns, and then further elution with 1-10% Et2O/petroleum ether gave 2-chloro-5-(ethoxymethoxy)pyrimidine (108) (1.27 g, 88%) as an oil; 1H NMR (CDCl3) delta 8.43 (s, 2H), 5.27 (s, 2H), 3.74 (q, J=7.1 Hz, 2H), 1.23 (t, J=7.1 Hz, 3 H); HRESIMS calcd for C7H10ClN2O2 m/z [M+H]+ 191.0396, 189.0425, found 191.0397, 189.0426.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4983-28-2, its application will become more common.

Reference:
Patent; Global Alliance for TB Drug Development; US2011/28466; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 73418-88-9, 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. 73418-88-9, name is Methyl 5-aminopyrimidine-2-carboxylate. A new synthetic method of this compound is introduced below.

Methyl 5-aminopyrimidine-2-carboxylate (10.29 mg, 0.067 mmol) and pyridine (0.049 mL, 0.611 mmol) were dissolved in DCM (2 mL) Intermediate 816C (0.030 g, 0.06 1 mmol) was added as a solution in DCM (1 mL). The reaction mixture was allowedto stir for 1 hour. The reaction mixture was concentrated under reduced pressure and purified on ISCO using 24 g column eluting with 0-100% EtOAc over 15 mm to yield Intermediate 816D (24.6 mg, 0.040 mmol, 66.3 % yield) as a pale yellow solid. ?HNIVIR (400MHz, CDC13) 8.47 (d, J=1.8 Hz, 3H), 8.44 (s, 1H), 7.91 (d, J10.3 Hz, 1H), 7.66 (s, 1H), 7.13 (s, 1H), 5.70-5.60 (m, 1H), 5.31 (br. s., 1H), 2.56 (s, 3H), 1.41 (d, J=6.8 Hz,5H), 1.17 (s, 3H), 0.07-0.11 (m, 6H). LC-MS. method H, RT = 1.27 mm, MS (ESI)m/z:608.0 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,73418-88-9, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; BATES, J. Alex; HALPERN, Oz Scott; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (1137 pag.)WO2018/13774; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia