Pyrimidines

Related Products of 1780-31-0 , The common heterocyclic compound, 1780-31-0, name is 2,4-Dichloro-5-methylpyrimidine, molecular formula is C5H4Cl2N2, 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 84[4-(6-Bromobenzo[b]thiophen-2-yl)-5-methylpyrimidin-2-yl]-[3-(4-methylpiperazin-1-yl)-propyl]-amine tri-hydrochloride(A). Preparation of 2-chloro-5-methylpyrimidine; Into a 3-necked, 500 mL round bottomed flask is added 2,4-dichloro-5-methylpyrimidine (25.0 g, 153 mmol), THF (125 mL) and zinc powder (30.1 g, 460 mmol). The mixture is heated to reflux and acetic acid (HOAc) (9.21 g, 153 mmol) in THF (20 mL) is dropwise added over 1 hour. After 1.5 hours at reflux, additional HOAc (3.93 g, 65.5 mmol) in THF (12.5 mL) is added over 10 minutes, and the mixture is refluxed for an additional 1 hour. The mixture is filtered over celite, rinsed with THF (150 mL) and the organic layers are concentrated under reduced pressure. The crude mixture is partitioned in EtOAc/dichloromethane/1 N NaOH and filtered. The organic layer is concentrated under reduced pressure to yield a peach colored solid. The crude material is subjected to chromatography on silica (in hexane) to provide the title compound as a white solid (13.5 g, 69% yield).

The synthetic route of 1780-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dahnke, Karl Robert; Lin, Ho-Shen; Richett, Michael Enrico; Shih, Chuan; Wang, Q May; Zhang, Bo; US2008/306082; (2008); A1;,
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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. 13162-26-0, name is 2,4-Dichloro-6-methyl-5-nitropyrimidine, the common compound, a new synthetic route is introduced below. SDS of cas: 13162-26-0

To a solution of 2,4-dichloro-6-methyl-5-nitropyrimidine (7 g, 34 mmol) and CH3COOK (9.8 g, 100 mmol) in MeOH (150 mL) was added Pd C (3 g). The mixture was stirred at H2 atmosphere for overnight. The reaction mixture was filtered, and the solvent was concentrated under reduced pressure to give the product 4-methylpyrimidin-5 -amine (1.5 g, 43%), which was used to next step without furthermore purification. ‘HNMR: MeOD 400MHz ? 8.28(s, 1H), 8.04(s, 1H), 2.3 l(s, 3H).

The synthetic route of 13162-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; SKELTON, Nicholas; GRADL, Stefan; BLAKE, James F.; GRAHAM, James M.; GUNAWARDANA, Indrani W.; HENTEMANN, Martin; MARLOW, Allison L.; TANG, Tony P.; WO2013/78254; (2013); A1;,
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Reference of 932-52-5, 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. 932-52-5, name is 5-Aminopyrimidine-2,4(1H,3H)-dione. A new synthetic method of this compound is introduced below.

General procedure: To a solution of 2a,b (5 mmol) in phosphorus oxychloride (10 ml) was added a solution of the appropriate amine (5 mmol) and phosphorus pentoxide (5 mmol) in phosphorus oxychloride (5 ml), and the mixture was refluxed for 5 h. After cooling, the reaction mixture was poured onto ice/water and neutralized with 5% sodium hydroxide solution; the formed precipitate was filtered, washed with water and crystallized from the ethanol.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,932-52-5, 5-Aminopyrimidine-2,4(1H,3H)-dione, and friends who are interested can also refer to it.

Reference:
Article; Abbas, Safinaz E.; Abdel Gawad, Nagwa M.; George, Riham F.; Akar, Yahya A.; European Journal of Medicinal Chemistry; vol. 65; (2013); p. 195 – 204;,
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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. 10132-07-7, name is 4-Amino-2,6-dichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 10132-07-7

EXAMPLE A 2-(N’-carbethoxy-piperazino)-4-chloro-6-amino-pyrimidine 29.0 gm of 2,4 -dichloro-6-aminopyrimidine [H. Bretschneider et al, Monatsh. f. Chemie 92, 132 (1961)]were suspended in 150 ml of dioxane, the suspension was heated to 80C, and 60.2 gm of N-carbethoxy-piperazine were added. After standing for 40 minutes at this temperature, the mixture was poured into 500 ml of water, and the aqueous solution was on an ice bath while stirring. The initially oily precipitating product crystallized after about 15 minutes. The crystals were suction-filtered off and recrystallized from 300 ml of methanol. Yield: 28.8 gm (57.3% of theory); m.p. 163-166C.

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, 10132-07-7, 4-Amino-2,6-dichloropyrimidine.

Reference:
Patent; Boehringer Ingelheim GmbH; US3975384; (1976); A;,
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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. 2915-16-4, name is 2-Chloro-4,6-diphenylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. name: 2-Chloro-4,6-diphenylpyrimidine

20 g (48.7 mmol) of the intermediate 1-4 was dissolved in 0.17 L of tetrahydrofuran (THF) under a nitrogen atmosphere, 13.0 g (48.7 mmol) of 2-chloro-4,6-diphenylpyrimidine and 1.69 g (1.46 mmol) of tetrakis(triphenylphosphine)palladium were added thereto, and the mixture was agitated. 16.8 g (122 mmol) of potassium carbonate saturated in water was added thereto, and the obtained mixture was heated and refluxed at 80 C for 6 hours. When the reaction was complete, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM) and treated with anhydrous MgSO4 to remove moisture and then, filtered and concentrated under a reduced pressure. Then, a residue obtained therefrom was separated and purified through flash column chromatography, obtaining 22.8 g (91 %) of the compound 2. (0170) HRMS (70 eV, EI+): m/z calcd for C37H26N2O: 514.2045, found: 514. (0171) Elemental Analysis: C, 86 %; H, 5 %

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, 2915-16-4, 2-Chloro-4,6-diphenylpyrimidine.

Reference:
Patent; Cheil Industries Inc.; LEE, Han-Ill; YU, Eun-Sun; KANG, Dong-Min; KANG, Eui-Su; MIN, Soo-Hyun; YANG, Yong-Tak; OH, Jae-Jin; RYU, Dong-Kyu; LEE, Sang-Shin; JANG, Yu-Na; JEONG, Soo-Young; JO, Young-Kyoung; HAN, Su-Jin; HONG, Jin-Seok; EP2952511; (2015); A1;,
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Electric Literature of 955368-90-8 ,Some common heterocyclic compound, 955368-90-8, molecular formula is C9H10N4OS, 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.

Compound 51-1 (2.00 g, 9.90 mmol) and Intermediate I1 (2.20 g, 9.90 mmol) were added into 1,4-dioxane solution, then N,N’-diethylethylenediamine (1.27 g, 10.89 mmol), potassium carbonate (1.37 g, 9.90 mmol) and cuprous iodide (1.89 g, 9.90 mmol) were added sequentially under nitrogen atmosphere, the temperature was raised to 95C and the reaction was stirred at reflux for 12 hours until it was complete. Then the mixture was cooled down to r.t. and concentrated, quenched by 50 mL water, then extracted by 50 mL EA, the organic phase was washed by 50 mL saturated brine, dried over anhydrous sodium sulfate, then filtered, evaporated and purified by chromatography (EA /PE =1/10-1/4) to give 51-2. 1H NMR (400MHz, CDCl3) delta 8.90 (s, 1H), 7.75 -7.71 (m, 1H), 7.35 (d, J=8.0 Hz, 1H), 6.67 (d, J=8.2 Hz, 1H), 5.71 – 5.64 (m,1H), 5.04 (dd, J=10.0 Hz, 1H), 5.05 – 4.80 (m,1H), 4.81 (d, J=6.4 Hz, 1H), 4.34 -4.29 (m, 2H), 2.55 (s, 3H), 1.56 (d, J=2.4 Hz, 1H), 1.42 – 1.38 (m, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,955368-90-8, its application will become more common.

Reference:
Patent; Shijiazhuang Sagacity New Drug Development Co., Ltd.; QIAN, Wenyuan; YANG, Chundao; LI, Zhengwei; LI, Jie; LI, Jian; CHEN, Shuhui; (137 pag.)EP3572413; (2019); A1;,
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Related Products of 5604-46-6, 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. 5604-46-6, name is 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde. A new synthetic method of this compound is introduced below.

Step 1 ; 1- (2-Amino-4, 6-dichloro-pyrimidin-5-yl) -ethanol A fine suspension OF 2-AMINO-4, 6-DICHLORO-PYRIMIDINE-5-CARBALDEHYDE (3.0 g, 15 mmol); (Seela, F.; Stecker, H. Helv. Chim. Acta 1986, 69, 1602) in THF was cooled to- 78 C. A 3M solution of MeMgBr in THF (25 mL, 75 mmol, 5 equiv. ) was added over 3 h, keeping the internal temperature AT-78 C. The mixture was stirred for a further 0.5 h, quenched with 100 ml H20, and neutralized with aw. HC1. Extraction (EtOAc) gave 1- (2-AMINO-4, 6-dichloro-pyrimidin-5-yl) -ethanol as a pale yellow solid (2.5 g, 76%) which was used without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5604-46-6, 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; CONFORMA THERAPEUTICS CORPORATION; WO2005/28434; (2005); A2;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 83410-16-6, 4-Chloro-5-iodo-2,6-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, Safety of 4-Chloro-5-iodo-2,6-dimethylpyrimidine, blongs to pyrimidines compound. Safety of 4-Chloro-5-iodo-2,6-dimethylpyrimidine

Step C: A mixture of 3-ethynyl-7-fluoro-2H-chromen-2-one (376 mg, 2.0 mmol), 4-chloro-5-iodo-2,6-dimethylpyrimidine (590 mg, 2.2 mmol), copper(I) iodide (19 mg, 0.1 mmol), bis(triphenylphosphine)palladium(II) dichloride (70 mg, 0.1 mmol), triethylamine (404 mg, 4.0 mmol) and CH3CN (4.0 mL) was stirred at 50 C. under an Argon atmosphere overnight, then the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (5% MeOH in CH2Cl2) to give 3-((4-chloro-2,6-dimethylpyrimidin-5-yl)ethynyl)-7-fluoro-2H-chromen-2-one (92 mg, 14%). MS m/z 329.3 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,83410-16-6, 4-Chloro-5-iodo-2,6-dimethylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; PTC Therapeutics, Inc.; F. Hoffmann-La Roche AG; Woll, Matthew G.; Chen, Guangming; Choi, Soongyu; Dakka, Amal; Huang, Song; Karp, Gary Mitchell; Lee, Chang-Sun; Li, Chunshi; Narasimhan, Jana; Naryshkin, Nikolai; Paushkin, Sergey; Qi, Hongyan; Turpoff, Anthony A.; Weetall, Marla L.; Welch, Ellen; Yang, Tianle; Zhang, Nanjing; Zhang, Xiaoyan; Zhao, Xin; Pinard, Emmanuel; Ratni, Hasane; (317 pag.)US9617268; (2017); B2;,
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Pyrimidine – Wikipedia

Reference of 302964-08-5, 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. 302964-08-5, name is 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, molecular formula is C16H13Cl2N5OS, 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.

iV-(2-chloro-6-methylphenyl)-2-(2-methyl-6-(pyridm-3-yl)pyrimidin-4- ylamino)thiazole-5-carboxamideTo 2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6- methylphenyl)thiazole-5-carboxamide (30mg, 0.076mmol) THF (2.OmL) was added pyridin-3-ylboronic acid (11.2 mg, 0.091mmol), Pd(PPh3)4 (21.2 mg, 0.018 mmol) and Na2CO3 (2 M, 0.15 mL, 0.3mmol). The mixture was stirred under Argon for 5 min, and then the mixture was heated at 160 0C in microwave reactor for Ih. The reaction was cooled to room temperature and water was added, extracted with 10% MeOH in CHCl3 (3*20 mL). The organic layers was combined and concentrated under reduced pressure. The crude was purified with prep-HPLC to obtain the title compound as a yellow solid. LC-ESIMS observed [M+H]+ 437.2 ; 1H NMR (400 MHz, DMSO-d6) delta 12.25 (broad s, IH), 10.01 (s, IH), 9.24 (s, IH), 8.78 (d, J= 5.2 Hz, IH), 8.48 (d, J= 8.0 Hz, IH), 8.33 (s, IH), 7.70-7.67 (m, IH), 7.42-7.41 (m, 2H), 7.32-7.25 (m, 2H), 2.71 (s, 3H), 2.26 (s, 3H).

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 302964-08-5, 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide.

Reference:
Patent; LIANG, Congxin; KOENIG, Marcel; HE, Yuanjun; WO2008/150446; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 945950-37-8, Adding some certain compound to certain chemical reactions, such as: 945950-37-8, name is 4-Methyl-7H-pyrrolo[2,3-d]pyrimidine,molecular formula is C7H7N3, 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 945950-37-8.

General procedure: To a mixture of appropriate 3a-e (1.5 mmol), 1 (1.57 mmol) and Ph3P (3.75 mmol) in THF was added DIAD (3.75 mmol) dropwise at 0 C under nitrogen and stirring continued at rt. Completion of reaction was analyzed by TLC, solvent evaporated under reduced pressure and crude was purified by column chromatography on silica gel by eluting up to 30 % ethyl acetate in hexane to give couple products in more than 80 % yield. The deprotection was carried out by heating at 60 C in 10 % HCl in MeOH. After completion (monitored by TLC), the reaction mixture was neutralized by NaHCO3 and purified by silica gel chromatography (10% methanol in DCM) to get 6a-e in 70-85% yield.

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. 945950-37-8, 4-Methyl-7H-pyrrolo[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Thiyagarajan, Anandarajan; Salim, Mohammed T.A.; Balaraju, Tuniki; Bal, Chandralata; Baba, Masanori; Sharon, Ashoke; Bioorganic and Medicinal Chemistry Letters; vol. 22; 24; (2012); p. 7742 – 7747;,
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