Pyrimidines

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 6299-25-8, name is 4,6-Dichloro-2-(methylthio)pyrimidine, the common compound, a new synthetic route is introduced below. Recommanded Product: 6299-25-8

Example 2C4,6-dichloro-2-(methylthio)pyrimidine-5-carboxylic acid; To a solution of diisopropylamine (20 mL, 142 mmol) in tetrahydrofuran (170 mL) at -78C was added n-butyl lithium (55.4 mL, 2.5M solution in hexane, 138 mmol). The mixture was stirred at -78C for 1 hour and was charged with a solution of the product of Example 2B (18 g, 92.3 mmol) in tetrahydrofuran (40 mL). After stirring at -78C for 3 hours, dry carbon dioxide was bubbled into the mixture for 30 minutes, followed by the addition of water at low temperature. The mixture was allowed to warm to ambient temperature and the mixture was adjusted to pH = 1 by addition of 2M hydrochloric acid. The mixture was extracted with ethyl acetate (3 x 300 mL) and the combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was washed with toluene to obtain the title compound. MS: 239 (M+H+).

The synthetic route of 6299-25-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; VASUDEVAN, Anil; PENNING, Thomas; CHEN, Huanming; LIANG, Bo; WANG, Shaohui; WU, Fengchun; SHEN, Yan; LIU, Cuihua; ZOU, Zhenguang; WO2012/97478; (2012); A1;,
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Pyrimidine – Wikipedia

Related Products of 938443-20-0, 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.938443-20-0, name is 2,4,7-Trichloropyrido[2,3-d]pyrimidine, molecular formula is C7H2Cl3N3, molecular weight is 234.4699, as common compound, the synthetic route is as follows.

The 2,4,7-trichloro-pyrido [2,3-d] pyrimidine (1g, 4.29mmol), and 8-oxa-3-azabicyclo [3.2.1] nonane hydrochloride (640mg, 4.29 mmol) were dissolved 20mLDCM added dropwise DIEA (0.9mL, 5.15mmol) under ice-cooling.After the reaction was stirred at room temperature for 18H, reaction mixture was washed, the organic layer was dried and concentrated to give a solid, which was used without purification was used directly in the next reaction.

The chemical industry reduces the impact on the environment during synthesis 938443-20-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shandong Xuanzhu Pharmaceutical Technology co., LTD; WU, YONG QIAN; WANG, AI CHEN; (35 pag.)CN102887895; (2016); B;,
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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.635698-56-5, name is tert-Butyl 2,4-dichloro-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate, molecular formula is C12H15Cl2N3O2, molecular weight is 304.17, as common compound, the synthetic route is as follows.name: tert-Butyl 2,4-dichloro-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

To the mixture of tert-butyl 2,4-dichloro-7, 8-dihydropyrido[4,3 -d]pyrimidine6(5H)-carboxylate (4.00 g, 13.15 mmol) in CH2C12 (15.00 mL) was added HC1/dioxane (4 N,15.00 mL). The mixture was stirred at 15 C for 15 h. LCMS showed one main peak of desired product and about 5% of starting material. The mixture was stirred at 30 C for 1 h. LCMS showed desired product was major. The mixture was concentrated under reduced pressure to afford the title compound (3.07 g, crude, HC1 salt) as a white solid which was used in the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,635698-56-5, tert-Butyl 2,4-dichloro-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; KADMON CORPORATION, LLC; OLSZEWSKI, Kellen; POYUROVSKY, Masha; BARSOTTI, Anthony; KIM, Ji-In; LIU, Kevin; MORRIS, Koi; (143 pag.)WO2016/210331; (2016); A1;,
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Electric Literature of 23631-02-9, 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. 23631-02-9, name is 4-Chloro-N,N-dimethylpyrimidin-2-amine. A new synthetic method of this compound is introduced below.

A mixture of N-(cis-4-bromo-2-trifluoromethoxy-benzyl)-cyclohexane-1, 4- diamine obtained in step B of example 1 (466 mg), (4-chloro-pyrimidin-2-yl)-dimethyl- amine (200 mg), and BuOH (1 mL) was stirred at reflux for 13 hr. The mixture was poured into saturated aqueous NaHC03 and the aqueous) layer was extracted with CHC13 (three times). The combined organic layer was dried over MgS04, filtered, concentrated under reduced pressure, and purified by flash chromttography (NH-silica gel, 20% EtOAc in) to give N4-(cis-4-{[4-bromo-2-(trifluoromethoxy) benzyl] arnino}-cyclohexyl)-Na, N2- dimethylpyrimidine-2, 4-diamine. To a solution of the above material in EtOAc (2 mL) was added 4 M hydrogen chloride in EtOAc (10 mL). The mixture was stirred at ambient temperature for 1 hr and concentrated under reduced pressure The residue was suspended in Et20 (20 mL) and the suspension was stirred at ambient temperature for 4 hr. The precipitate was collected by filtration, washed with Et2O, and dried under reduced pressure to give N4-(cis-4-{ [4-bromo-2-(trifluoromethoxy) benzyl]-amino} cyclohexyl)-N2, N2- dimethylpyrimidine-2, 4-diamine dihydrochloride (294 mg). ESI MS m/e 488, M (free) + H+ ;’H NMR (300 MHz, CDCI3) 8 1.42-1. 67 (m, 2 H), 2.03- 2.39 (m, 6 H), 2. 79-3.38 (m, 7 H), 4.13-4. 36 (m, 3 H), 6.89-7. 00 (m, 1 H), 7.42-7. 46 (m, 1 H), 7.50-7. 57 (m, 1 H), 7. 90-8. 01 (m, 1 H), 8.12 (d, J= 8.4 Hz, 1 H), 8.90-9. 00 (m, 1 H), 9.98-10. 18 (m, 2 H), 12.21-12. 37 (m, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,23631-02-9, 4-Chloro-N,N-dimethylpyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; Arena Pharmaceuticals, Inc; WO2005/95357; (2005); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1722-12-9 ,Some common heterocyclic compound, 1722-12-9, molecular formula is C4H3ClN2, 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 5 Synthesis of HK-9, HK-11, HK-13 and HK-15 The following describes the general synthesis of 2-(pyrrolidine-1-yl)pyrimidine (HK-9), 4,6-dimethoxy-2-(pyrrolidine-1-yl)pyrimidine, HK-11, 2-(piperidine-1-yl)pyrimidine (HK-13), 4,6-dimethoxy-2-(piperidine-1-yl)pyrimidine (HK-15), 5-benzyloxy-2-(pyrrolidine-1-yl)pyrimidine (Compound 35), 5-benzyloxy-2-(piperidine-1-yl)pyrimidine (Compound 36), 5-benzyloxy-4,6-dimethoxy-2-(pyrrolidine-1-yl)pyrimidine (Compound 37), and 5-benzyloxy-4,6-dimethoxy-2-(piperidine-1-yl)pyrimidine (Compound 38). Referring to the reaction scheme of , to 9.53 mL (116 mmol) pyrrolidine (29) in 400 mL of anhydrous THF was added 2.78 g of sodium hydride (116 mmol) and the mixture was refluxed for 0.5 hr. After cooling to r.t., 12 g (105 mmol) of 2-chloropyrimidine (33) was added dropwise and the mixture was refluxed for 2 days and then cooled in an ice bath. Water (200 mL) was then added to the cooled reaction mixture and the THF was removed in vacuo. The aqueous residue was extracted with CHCl3 and the combined CHCl3 extracts were washed with brine, dried over magnesium sulfate, and filtered. After removal of solvent in vacuo, the residue was purified by silica gel column chromatography using 20:1 hexanes:EtOAc as eluent. The product was then recrystallized from diethyl ether (Et2O) to give a 12.0 g (76%) of HK-9 as a yellow solid, mp 39.0-39.6 C. 1H NMR (CDCl3) delta 8.31 (d, J=4.88 Hz, 2H), 6.45 (t, J=4.88 Hz, 1H), 3.57 (t, J=4.4 Hz, 4H), 2.01-1.98 (m, 4H). Anal. Calcd for C8H11N3; C, 64.40; H, 7.43; N, 28.16. Found: C, 64.42; H, 7.53; N, 27.97.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1722-12-9, its application will become more common.

Reference:
Patent; KADOR, PETER F.; US2014/235858; (2014); 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. 5018-41-7, name is 4-Amino-6-chloro-5-methoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 5018-41-7

6-(4-(1 -(2-(azetidin-1 -yl)ethyl)-4-(2-(thfluoromethyl)Dvhdin-4-yl)-1 H-imidazol-2- yl)piperidin-1 -yl)-5-methoxypyrimidin-4-amine (“1 15”) A reaction mixture of 6-Chloro-5-methoxy-pyrimidin-4-ylamine (45.00 mg; 0.28 mmol; 1 .00 eq.), 4-[1 -(2-Azetidin-1 -yl-ethyl)-2-piperidin-4-yl-1 H-imidazol-4-yl]-2- trifluoromethyl-pyridine hydrochloride (4) (148.13 mg; 0.28 mmol; 1 .00 eq.), and Cs2C03 (367.53 mg; 1 .13 mmol; 4.00 eq.) in DMSO 1 .0ml was stirred at 120C for 2days, purified by HPLC collected title compound 17mg. LC-MS: (M+1 = 503, obsd. = 503).

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, 5018-41-7, 4-Amino-6-chloro-5-methoxypyrimidine.

Reference:
Patent; MERCK PATENT GMBH; LAN, Ruoxi; HUCK, Bayard R.; CHEN, Xiaoling; XIAO, Yufang; DESELM, Lizbeth Celeste; QIU, Hui; NEAGU, Constantin; BANKSTON, Donald; JONES, Christopher Charles Victor; WO2013/40059; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 14331-54-5, 2,4-Dimethylpyrimidine, 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: 2,4-Dimethylpyrimidine, blongs to pyrimidines compound. Recommanded Product: 2,4-Dimethylpyrimidine

2-Chloro-4-methyl-pyrimidine. A mixture of 2,6-dichloropyrimidine (1.5 g, 10.07 mmol), trimethylaluminum (0.87 g, 12.08 mmol), tetrakis(triphenylphosphine)palladium(0) (0.81 g, 0.7 mmol) in THF (30 mL) was heated under reflux for several hours. The reultant mixture was quenched with addition of water. (Note: allowing reaction to go overnight was detrimental). The product mixture was extracted with ethyl acetate three times, dried over sodium sulfate, filtered and concentrated to give a dark yellow oil. The resultant oil was purified by flash chromatography on silica gel (hexane/ethyl acetate) to give title compound as a light yellow solid. 1H NMR (400 MHz, DMSO) delta 8.62-8.61 (d, j=5.1 Hz, 1 H), 7.47-7.46 (d, j=5.1 Hz, 1 H), 2.56 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14331-54-5, 2,4-Dimethylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Payne, Linda S.; Tran, Lekhanh O.; Zhuang, Linghang H.; Young, Steven D.; Egbertson, Melissa S.; Wai, John S.; Embrey, Mark W.; Fisher, Thorsten E.; Guare, James P.; Langford, H. Marie; Melamed, Jeffrey Y.; Clark, David L.; US2003/229079; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1260169-02-5, 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 1260169-02-5, name is Ethyl 2-aminopyrazolo[1,5-a]pyrimidine-3-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

2-Aminopyrazolo [1,5-a] pyrimidine-3-carboxylic acidEthyl ester (1.60 g, 7.76 mmol),4-dimethylaminopyridine (0.19 g, 1.55 mmol)And triethylamine (3.25 mL, 23.28 mmol)Dissolved in dichloromethane (15 mL)And di-tert-butyl dicarbonate (3.30 mL, 15.52 mmol) was added thereto.After the resultant reaction solution was stirred at room temperature for 3 hours,Concentrate under reduced pressure.The resulting residue was purified by silica gel column chromatography (100% dichloromethane)The title compound was obtained as a yellow solid (1.24 g, 52.1%).

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 1260169-02-5, Ethyl 2-aminopyrazolo[1,5-a]pyrimidine-3-carboxylate.

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

Adding a certain compound to certain chemical reactions, such as: 1193-21-1, 4,6-Dichloropyrimidine, 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-phenylpyrimidineN-Butyl lithium (3.22 g, 50.3 mmol, and 1.6N in hexane) was added dropwise to a stirred solution of bromobenzene (7.9 g, 50.3 mmol) in THF (70 mL) over a period of 30 min at -78 ¡ãC, and reaction was continued stirring for 2 h. The generated phenyl lithium was added dropwise to a stirred solution of 4, 6-dichloropyrimidine (5 g, 33.5 mmol) in THF (50 mL) over a period of 45 min at -78 0C, and reaction was continued stirring for 30 min. Then, the reaction mixture was slowly heated to 0 ¡ãC and quenched with water (100 ml), DDQ (7 g, 30. 8 mmol) dissolved in THF (70 mL) was added portionwise and stirred for 10 min. Then, the reaction mixture was washed with 10percent NaOH (50 mL), extracted with CH2Cl2 (3×100 mL), washed with brine (100 mL), dried (Na2SO4) and concentrated. The concentrated product was purified through silica column chromatography using pet. ether to afford 4,6-dichloro-2- phenylpyrmimidine (example 21, 2.6 g, 35 percent) as a white solid. Rf: 0.3 (100percent PE). 1H NMR (400 MHz, CD3OD): delta 8.41-8.39 (m, 2H), 7.60 (s, IH), 7.58-7.50 (m, 3H). m/e (M+l): 224.8.

The synthetic route of 1193-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MIIKANA THERAPEUTICS, INC.; WO2008/154026; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 6214-47-7, Adding some certain compound to certain chemical reactions, such as: 6214-47-7, name is Ethyl 2-(4-chloropyrimidin-5-yl)acetate,molecular formula is C8H9ClN2O2, 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 6214-47-7.

To a nitrogen de-gassed solution of ethyl 2-(4-chloropyrimidin-5-yi)acetate {1108) (0.823 g, 4.10 mmol) in dry DMF (15 mL) were added triethylamine (1.715 mL, 12.31 mmoi) followed by triphenylphosphine (0.124 g, 0.473 mmol), trans- dichlorobis(triphenyl-phosphine)pailadium(ll) (0.144 g, 0.205 mmoi), Cu(l)l (0,078 g, 0.410 mmol) and finally (triethyisilyi)acetylene (1.470 mL, 8.204 mmol). The reaction mixture was then heated under microwave irradiation at 120 C for 25 minutes, concentrated in vacuo and purified by silica gel chromatography (isoiera Biofage, 40 g Si cartridge, 0-30% EtOAc in petroleum benzine 40-60 C) to give the title compound (1109) (1.176 g, 94% yield) as a yellow-orange oil; 1H NMR (400 MHz, CDCI3) delta 9.08 (s, 1 H), 8.68 (s, 1 H), 4.18 (q, J = 7.1 Hz, 2H), 3.80 (s, 2H), 1.26 (t, J = 7.1 Hz, 3H), 1.10 – 1.01 (m, 9H), 0.77 – 0.67 (m, 6H) LCMS Method C: rt 6.64 min; m/z 305.1 [M+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. 6214-47-7, Ethyl 2-(4-chloropyrimidin-5-yl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LTD; DEVLIN, Mark Graeme; STREET, Ian Philip; TONG, Warwick Bonner; WO2014/27199; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia