Day: March 23, 2022

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 16372-08-0, name is 4-Chloro-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

General procedure: A mixture of dimethyl-[2-piperazin-1 -yl-2-(4-trifluoromethyl-phenyl)-ethyl]-amine (300.00 mg; 0.96 mmol; 1 .00 eq.), 4-Chloro-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine (156.52 mg; 0.96 mmol; 1 .00 eq.) and potassium carbonate (336.95 mg; 2.39 mmol; 2.50 eq.) in dry DMSO (3.00 ml) was irradiated at 1 90 °C for 3h. The reaction mixture was cooled to RT, diluted with water (25 ml_), and extracted with DCM (3 x 10ml). The combined organic layer was washed with water, brine solution, dried over Na2S04 and concentrated under vacuum. The resulted brown thick residue was purified by biotage using DCM/MeOH as an elutent to yield brown gum. This gum was further azeotroped with diethylether (2 x 10ml) to obtain foamy solid. Then this solid was further treated with diethyl ether/hexane mixture (1 :1 , 5ml). The solventportion was syringed out and the remaining solid was further dried under vacuum to afford the title compound as pale brown solid (34.00 mg, 8.2 percent yield). LC- MS (M+H = 421 , obsd. = 421 ); 1 H NMR (400 MHz, DMSO-d6) delta [ppm]: 7.80 (s, 1 H), 7.67 (d, J = 7.7 Hz, 2H), 7.50 (d, J = 8.1 Hz, 2H), 6.56 (bs, 1 H), 3.76 (s, 1 H), 3.50-3.48 (m, 4H), 3.37 (bs, 2H), 3.01 (t, J = 8.6 Hz, 2H), 2.79 (bs, 2H), 2.50-2.49 (m, 1 H), 2.39 (bs, 4H), 2.10 (bs, 6H).

With the rapid development of chemical substances, we look forward to future research findings about 16372-08-0.

Reference:
Patent; MERCK PATENT GMBH; LAN, Ruoxi; HUCK, Bayard R.; CHEN, Xiaoling; XIAO, Yufang; WO2014/78637; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 115932-00-8, Adding some certain compound to certain chemical reactions, such as: 115932-00-8, name is Ethyl pyrazolo[1,5-a]pyrimidine-3-carboxylate,molecular formula is C9H9N3O2, 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 115932-00-8.

To a solution of pyrazolo [1,5-a] pyrimidine-3-carboxylic acid ethyl ester (3.15 g, 16.4 mmol)In ethanol (50 mL) and water (40 mL)Aqueous potassium hydroxide (2M, 40 mL) was added,The resulting reaction was stirred at 50 C for 2 hours,Cool to room temperature and concentrate under reduced pressure. A 1 M aqueous solution of dilute hydrochloric acid was added to the resulting reaction mixture to adjust to pH = 2. A white solid appeared and was filtered. The filter cake was collected to give the title compound as a white solid (2.6 g, 97%).

According to the analysis of related databases, 115932-00-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; (88 pag.)CN104650092; (2017); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 34253-03-7, 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. 34253-03-7, name is Methyl pyrimidine-2-carboxylate. A new synthetic method of this compound is introduced below.

Pyrimidin-2-ylmethanol (12):To a stirred solution of ester 11 (0.43 g, 3.09 mmol) in EtOH (30 mL), cooled to 0C, NaBH4 (0.114 g, 3.09 mmol) was added and stirred for 2 h. After consumption of the starting material (by TLC), the reaction was quenched with cold water and concentrated under vacuo to give the crude material which was purified by silica gel column chromatography (MeOH/CH2Cl2 1 :49) to afford alcohol 12 (0.145 g, 37%) as syrup.TLC: 10% MeOH/CHCl3 (Rf: 0.3)1H NMR (500MHz, CDC13): delta 8.75 (d, J = 5.5 Hz, 2H), 7.26-7.22 (m, 1H), 4.85 (s, 2H).Mass (ESI): 111.1 [M++l].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,34253-03-7, Methyl pyrimidine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; THERACRINE, INC.; SUN, Lijun; BARSOUM, James; WESTER, Ronald; WO2013/13238; (2013); A2;,
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. 17326-27-1, name is 2-Chloro-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde, molecular formula is C10H7ClN2O2, 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. COA of Formula: C10H7ClN2O2

G2 (0.5 mmol) was dissolved in 10.4 mL of tert-butyl alcohol and 2.5 mL of 2-methyl-2-butene. A solution of sodium chlorite (4.59 mmol) and sodium dihydrogenphosphate (3.46 mmol) in 4.2 mL of water was added dropwise. The reaction mixture was stirred at room temperature overnight. Volatile components were then removed under vacuum, and the residue was dissolved in 10 ml of water and extracted with two 10 ml portions of hexane. The aqueous layer was acidified to pH=3 with HCl(aq) and extracted with 10 mL portions of methylene chloride. The combined organic layers were washed with 20 mL of cold water, dried and concentrated to give G4. 1H NMR (400 MHz, DMSO-d6) delta 2.58 (s, 3H), 7.53 (t, J=7.0 Hz, 1H), 8.14 (d, J=7.2 Hz, 1H), 8.97 (d. J=6.8 Hz, 1H), 13.53 (brs, 1H); 13C NMR (100 MHz, DMSO-d6) delta 16.7, 108.1, 117.1, 125.6, 133.3, 138.7, 148.2, 152.0, 154.6, 163.9.

With the rapid development of chemical substances, we look forward to future research findings about 17326-27-1.

Reference:
Patent; Brodin, Priscille; Christophe, Thierry; No, Zaesung; Kim, Jaeseung; Genovesio, Auguste; Fenistein, Denis Philippe Cedric; Jeon, Heekyoung; Ewann, Fanny Anne; Kang, Sunhee; Lee, Saeyeon; Seo, Min Jung; Park, Eunjung; Contreras Dominguez, Monica; Nam, Ji Youn; Kim, Eun Hye; US2011/178077; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 40497-30-1, name is 2-Methylpyrimidine-4,6(1H,5H)-dione. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 40497-30-1

FOX-7 was synthesized according to the method using the procedure of Fu [9]. 2-methylpyrimidine-4,6-dione (2.53 g,0.02 mol) was dissolved in 12mL concentrated H2SO4 (98%), and then 4mL Nitric acid fuming (98%) was dripped in the mixture. The reaction mixture was kept under 15C. After 3 h, the mixture was poured into ice water. The yellow precipitate formed, which was filtered and dried 5 h under vacuum at 50C, yielding 2.40 g (81.1%).The yellow crystal was obtained from C2H5OH solvent. IR (KBr,nu /cm-1): 3407, 3321, 3294, 3216, 1622, 1501, 1473, 1388, 1328, 1201,1161, 1133, 1020, 620, 453 cm-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, 40497-30-1, 2-Methylpyrimidine-4,6(1H,5H)-dione.

Reference:
Article; Li, Keyao; Ren, Xiangwen; Fu, Shuqin; Zhu, Jiaping; Journal of Molecular Structure; vol. 1173; (2018); p. 26 – 32;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 313339-35-4, 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid, 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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

4,6-dichloro-2-(methylthio)pyrimidine-5-carboxylic acid (Compound of Reference Example 1; 3.59g) and N, N-dimethylformamide (0.2mL) were added to thionyl chloride (11ml_). While heated, the mixture was refluxed for 2 hours. The reaction mixture was then distilled under reduced pressure to obtain a yellow residue. Meanwhile, 1-(t-butoxycarbonylamino)-3-[3,5-(trifluoromethyl)benzylamino]propane (Compound of Refer-ence Example 2; 6.61 g) was dissolved in tetrahydrofuran (40mL) along with triethylamine (10ml_). While this solution was chilled on an ice bath, a tetrahydrofuran solution of the yellow residue (10ml) obtained above was added. The mixture was stirred for 1 hour and then additional 3 hours at room temperature. The reaction mixture was then diluted with ethyl acetate, was sequentially washed with water and a saturated aqueous solution of sodium chloride, and was then dried over anhydrous sodium sulfate. Following removal of the solvent, the residue was purified on a silica gelcolumn chromatography (ethyl acetate: hexane = 1: 3) to obtain N-[3,5-bis(trifluoromethyl)benzyl]-N-[3-(t-butoxycarb-onylamino)propyl]-4,6-dichloro-2-(methylthio)pyrimidine-5-carboxylic acid amide (8.49g, 91%). MS(FAB+)m/z: 621 (M+H+) HRMS(FAB+): Calcd for C23H25CI2F6N4O3S: 621.0929; found: 621.0938

At the same time, in my other blogs, there are other synthetic methods of this type of compound,313339-35-4, 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Kyorin Pharmaceutical Co., Ltd.; EP1496059; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 43024-61-9, name is Ethyl 7-hydroxypyrazolo[1,5-a]pyrimidine-6-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Safety of Ethyl 7-hydroxypyrazolo[1,5-a]pyrimidine-6-carboxylate

Ethyl 7-hydroxypyrazolo[1,5-a]pyrimidine-6-carboxylate () (3.20 g, 15.5 mmol) was dissolved in phosphorus oxychloride (30 mL), N,N-diisopropylethylamine (5.4 mL, 30.9 mmol) was added, and the mixture was stirred with heating at 100 C for 3 hr. After confirmation of consumption the starting materials, phosphorus oxychloride was evaporated under reduced pressure, and the residue was dissolved in ethyl acetate. The solution was added dropwise to a saturated aqueous sodium hydrogen carbonate solution under ice-cooling. To the saturated aqueous sodium hydrogen carbonate solution was added ethyl acetate, and the mixture was extracted 3 times. The combined organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.

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, 43024-61-9, Ethyl 7-hydroxypyrazolo[1,5-a]pyrimidine-6-carboxylate.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; YAMAMOTO, Keisuke; ARATAKE, Seiji; HEMMI, Kazuki; EP2543670; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 16097-60-2 ,Some common heterocyclic compound, 16097-60-2, molecular formula is C5H3ClF3N3, 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.

Example 21 4-(4-{[2-Amino-6-(trifluoromethyl)pyrimidin-4-yl]amino}-2-fluorobenzyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile 82 mg (0.31 mmol) of 4-(4-amino-2-fluorobenzyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile and 67 mg (0.34 mmol) of 4-chloro-6-trifluoromethylpyrimidine-2-amine are suspended in 3 ml of water, 1.5 ml of ethanol and 0.15 ml of 4N hydrochloric acid. The reaction mixture is heated at reflux for 2 hours. After cooling, the mixture is made alkaline using dilute aqueous sodium hydroxide solution, a little methanol is added, the mixture is extracted with ethyl acetate and the solvent is removed under reduced pressure. The residue is purified by preparative HPLC. This gives crystals. Yield: 111 mg (65% of theory) LC-MS (Method 3): Rt=2.34 min. MS (ESI pos.): m/z=428 [M+H]+. 1H-NMR (DMSO-d, 300 MHz): delta=4.41 (s, 2H), 6.35 (s, 1H), 6.90 (d, 1H), 6.96 (br. s, 2H), 7.14 (t, 1H), 7.32 (dd, 1H), 7.93 (dd, 1H), 8.29 (d, 1H), 8.46 (s, 1H), 9.77 (s, 1H), 12.86 (br. s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16097-60-2, its application will become more common.

Reference:
Patent; Bayer HealthCare AG; US2008/269268; (2008); 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.36314-98-4, name is 2-Amino-4-cyanopyrimidine, molecular formula is C5H4N4, molecular weight is 120.11, as common compound, the synthetic route is as follows.SDS of cas: 36314-98-4

Intermediate 1-11-4To a solution of 2-aminopyrimidine-4-carbonitrile (1 g, 8.3 mmol) in 7M NH3 in MeOH (25.5 mL) was added Raney-Nickel (50% wet, 1.955 g, 33 mmol) and stirred at RT under an H2 atmosphere (32.5 bar) for 22h. The reaction was filtered and concentrated to give the intermediate 1-11-4 (954 mg, 92%) which was used without further purification.1H-NMR (400 MHz ,DMSO-d6), Shift [ppm]= 3.55 (2H), 6.34-6.54 (2H), 6.63 (1H), 8.09- 8.21 (1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,36314-98-4, 2-Amino-4-cyanopyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; GRAHAM, Keith; KLAR, Ulrich; BRIEM, Hans; HITCHCOCK, Marion; BAeRFACKER, Lars; EIS, Knut; SCHULZE, Volker; SIEMEISTER, Gerhard; BONE, Wilhelm; SCHROeDER, Jens; HOLTON, Simon; LIENAU, Philip; TEMPEL, Rene; SONNENSCHEIN, Helmut; BALINT, Jozsef; GRAUBAUM, Heinz; (577 pag.)WO2015/193339; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 87253-62-1, 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. 87253-62-1, name is 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylic acid, molecular formula is C8H8N4O2, 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: In 25ml RB flask to a solution of Compound 9 (200 mg) in dry DMF (5ml), EDCI (250 mg, 1.25eq) and DMAP (130 mg,1eq) were added followed by addition of Sulfonamide (1eq). RM was stirred at RT for 4hrs. Solvent from the reaction mixture was evaporated. To the residue water was added and acidified with 6N HCl, solid precipitated out. Solid was filtered and dried. Crude solid was purified by flash chromatography eluating with 4-8% MeOH/DCM as solvent system to give pure product.

According to the analysis of related databases, 87253-62-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Patil, Vikas; Kale, Manoj; Raichurkar, Anandkumar; Bhaskar, Brahatheeswaran; Prahlad, Dwarakanath; Balganesh, Meenakshi; Nandan, Santosh; Shahul Hameed; Bioorganic and Medicinal Chemistry Letters; vol. 24; 9; (2014); p. 2222 – 2225;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia