Tag: M.W:100-200

Electric Literature of 105742-66-3, 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 105742-66-3, name is 4,5-Dichloro-2,6-dimethylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Compound 5 was synthesized as described.33 Compounds 6 and 7were synthesized in our previous work.34 Compounds 4 (5 mmol), 7(5 mmol) and anhydrous potassium carbonate (5 mmol, 0.69 g) wereadded to a mixed solvent of dimethyl formamide (20 mL) and water(10 mL), and then refluxed for 2-4 h. The progress was monitored byTLC. After the reaction was complete, the reaction solution was pouredinto saturated saline and extracted with ethyl acetate (3×80 mL). Theextract was dried, filtered, and the solvent was removed under reducedpressure to give a crude product. Recrystallization from the mixedsolvent of petroleum ether and ethyl acetate gave pure target compoundsO1-17 (Scheme 2).

According to the analysis of related databases, 105742-66-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yan, Zhongzhong; Liu, Aiping; Ou, Yingcan; Li, Jianming; Yi; Zhang, Ning; Liu, Minhua; Huang, Lu; Ren, Jianwei; Liu, Weidong; Hu, Aixi; Bioorganic and Medicinal Chemistry; vol. 27; 15; (2019); p. 3218 – 3228;,
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Application of 5413-85-4 ,Some common heterocyclic compound, 5413-85-4, molecular formula is C4H3Cl2N3, 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.

A suspension of 4, 6-dichloropyrimidin-5-amine (12 g, 73 mmol) and N2H4-H2O (20 g, 402 mmol, 5.5 eq. ) in THF (30 mL) was stirred at rt for 50 hours. The mixture was poured into water and filtered. The filter cake was washed with water to give 4-chloro-6-hydrazinylpyrimidin-5-amine (9 g, 79yield) as a white solid. LC-MS: m/z 160.2 (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. 5413-85-4, 5-Amino-4,6-dichloropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; TRAVINS, Jeremy, M.; KONTEATIS, Zenon, D.; SUI, Zhihua; YE, Zhixiong; (199 pag.)WO2018/39972; (2018); A1;,
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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. 13223-25-1, name is 2-Chloro-4,6-dimethoxypyrimidine, molecular formula is C6H7ClN2O2, 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: C6H7ClN2O2

Step 5) 4,6-dimethoxy-2-(piperazin-l-yl)pyrimidine To a mixture of 2-chloro-4,6-dimethoxypyrimidine (1.26 g, 7.2 mmol) in DMF (10 mL) were added potassium carbonate (1.00 g, 7.2 mmol) and anhydrous piperazine (1.24 g, 14.4 mmol). The reaction mixture was heated to 100 C and stirred for 10 hours. Then the reaction mixture was cooled to rt, diluted with water (10 mL) and extracted with EtOAc (20 mL x 3). The combined organic phases were dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (CLLC /MeOH (v/v) = 20/1) to give the title compound as yellow oil (1.05 g, 65.0%). The compound was characterized by the following spectroscopic data: LC-MS (ESI, pos. ion) m/z: 225.1 [M + H]+ and lH NMR (CDC13, 400 MHz) delta (ppm): 5.39 (s, 1H), 3.86 (s, 6H), 3.78 (t, J= 4.9 Hz, 4H), 3.47 (t, J = 5.0 Hz, 4H).

With the rapid development of chemical substances, we look forward to future research findings about 13223-25-1.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; JIN, Chuanfei; ZHOU, Rongqi; WO2015/14256; (2015); A1;,
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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. 22536-65-8, name is 2-Chloro-5-methoxypyrimidine. A new synthetic method of this compound is introduced below., Computed Properties of C5H5ClN2O

Prepare 1L four-necked flask with a stirring device and thermometer.Add 100 g of 2-chloro-5-methoxypyrimidine,300 mL of acetic acid was added to the reaction flask,Stir well, then add 153g of 48% hydrobromic acid and 1g of methionine.Warming up to reflux reaction for 5 h,Sampling HPLC controlled until the end of the reaction, product content 96%, dihydroxy by-product 0.5%;After dropping to room temperature, 300 mL of water was added to the reaction solution, and the mixture was extracted three times with 300 mL of dichloromethane.The organic phases were combined and washed with saturated sodium bicarbonate solution.Then, it is dried over anhydrous sodium sulfate, and after filtration, the organic phase is concentrated under reduced pressure to give a crude product;The crude product was recrystallized from the crude product to give a pale yellow solid, 82 g.The yield was 91% and the purity was 98%.

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, 22536-65-8, 2-Chloro-5-methoxypyrimidine.

Reference:
Patent; Haimen Ruiyi Pharmaceutical Technology Co., Ltd.; Xue Song; Zhou Wenjun; (5 pag.)CN110041269; (2019); A;,
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. 1161763-15-0, name is 4-Amino-6-bromo-2-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 4-Amino-6-bromo-2-methylpyrimidine

60% sodium hydride (12.0 g, 0.30 mol) was suspended in THF (300 mL) and cooled down to 0 C. 4-amino-6-bromo-2-methylpyrimidine (Compound 9) (18.7 g, 0.1 mol) was then added in batches and stirred for 30 min. After methyl 2-chlorothiazole-5-formate (Compound 10) (17.7 g, 0.1 mol) was added in batches, the reactants were heated and reacted by refluxing for 4 h, and then cooled down to room temperature for reaction overnight. When controlling the temperature between 0 C. and 5 C., hydrochloric acid (2N) was added for neutralization reaction. After adding keep heat and stirred to grow grains for 1 h. Filtrate and wash the cake with water, and then dry to give target Compound 11 (25.8 g, yield is 78.4%).[0177]Element analysis: C10H9BrN4O2S, Calculated: C, 36.49; H, 2.76; N, 17.02. Found: C, 36.51; H, 2.77; N, 16.99.[0178]1H-NMR (500 MHz, DMSO-d6): delta(ppm) 2.580 (s, 3H), 3.820 (s, 3H), 6.960 (S, 1H), 8.160 (s, 1H), 12.376 (s, 1H) (which disappeared after exchanging D2O)[0179]13C-NMR (500 MHz, DMSO-d6): delta(ppm) 25.700, 52.800, 104.161, 121.662, 146.010, 157.910, 159.124, 162.412, 162.949, 167.871.

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, 1161763-15-0, 4-Amino-6-bromo-2-methylpyrimidine.

Reference:
Patent; Nan Jing Cavendish Bio-Engineering Technology Co. Ltd.; Yan, Rong; Yang, Hao; Hou, Wen; Xu, Yongxiang; US2013/30177; (2013); A1;,
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Application of 38275-55-7, 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 38275-55-7 as follows.

Intermediate 5; l-(5-Fluoropyrimidin-2-yl)ethanoneTo a solution of 5-fluoropyrimidine-2-carbonitrile (Intermediate 4, 2.5 g) in Et2O (50 ml) at 00C was added drop-wise a solution of MeMgBr (12 ml, 3.0M in Et2O). The resulting solution was stirred at this temperature for 30 minutes, and was then allowed to warm to ambient temperature overnight. The mixture was quenched with a solution of saturated NH4Cl(aq) and extracted with Et2O. The organic extracts dried and evaporation gave a colored residue. Purification by column chromatography (ISCO, 3% MeOH/DCM) to afford the title compound (800 mg). 1H NMR (CDCl3) delta 8.75 (s, 2H), 2.77 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,38275-55-7, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/7753; (2009); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 3934-20-1 , The common heterocyclic compound, 3934-20-1, name is 2,4-Dichloropyrimidine, molecular formula is C4H2Cl2N2, 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.

To a solution of 2, 4-dichloro-pyrimidine (5. 00 g) in THF (50 mL) was added 70% aqueous EtNH2 (5.40 g). The mixture was stirred at ambient temperature for 1 hr and concentrated under reduced pressure. The residue was dissolved in CHCl3 and the solution was poured into saturated aqueous NaHC03. The two layers were separated and the aqueous layer was extracted with CHC13 (twice). The combined organic layer was dried over MgS04, filtered, concentrated under reduced pressure, and purified by flash chromatography (silica gel, 17% to 50% EtOAc in hexane) to give (2-chloro-pyrimidin-4- yl) -ethyl-amine (3.69 g) and (4-chloro-pyrimidin-2-yl)-ethyl-amine (1.28 g). (2-chloro-pyrimidin-4-yl)-ethyl-amine ; ESI MS m/e 157, M ;’H NMR (500 MHz, CD13) 8 1.26 (t, J= 7.3 Hz, 3 H), 3.16-3. 62 (m, 2 H), 4.80-5. 95 (m, 1 H), 6.23 (d, J= 5.8 Hz, 1 H), 8.02-8. 22 (m, 1 H). (4-chloro-pyrimidin-2-yl)-ethyl-amine ; CI MS m/e 158, M + H+ ;’H NMR (500 MHz, CDCIs) 8 1.23 (t, J= 7.5 Hz, 3 H), 3.42- 3.49 (m, 2 H), 5.30-5. 62 (m, 1 H), 6.54 (d, J= 5.2 Hz, 1 H), 8.02-8. 22 (m, 1 H).

The synthetic route of 3934-20-1 has been constantly updated, and we look forward to future research findings.

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

Electric Literature of 1753-50-0, 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 1753-50-0 as follows.

To a stirred solution of compound CS (0.5 g, 2.95 mmol) in ethanol (10 mL), 2-chloropyrimidine-5-carbonitrile (AF, 0.45 g, 3.25 mmol) and DIPEA (2.52 mL, 14.7 mmol) were added and the reaction mixture was heated to 90C for 16 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using 20% EtOAc/hexane to afford compound CT (0.61 g, 76%) as a white solid. LC-MS: m/z 272.05 [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,1753-50-0, its application will become more common.

Reference:
Patent; VPS-3, INC.; YATES, Christopher, M.; (397 pag.)WO2018/165520; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 37972-24-0, 2-Ethynylpyrimidine, 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, Application In Synthesis of 2-Ethynylpyrimidine, blongs to pyrimidines compound. Application In Synthesis of 2-Ethynylpyrimidine

General procedure: To a stirring solution of 3 (1 eq.) in MeOH (5 vol) was added alkyne(1 eq.) followed by 100 mM aq. CuSO4 (5 mol %) and 100 mM aq. sodium ascorbate (10 mol %). The reaction was poured into water (20 mL) and extracted with DCM (4 x 50 mL). The combined organics were washed with brine (50 mL), dried over anh. MgSO4 and filtered. The volatiles were removed in vacuo and the crude was purified by MPLC over C18 silica gel (Grace Reveleris X2, A: H2O+ 0.1% TFA, B: ACN + 0.1% TFA, 5-25%) then repurified (GraceReveleris X2, A: H2O + 0.1% TFA, B: ACN + 0.1% TFA, 5-100% B) togive a cream powder (16 mg, 9%). LCMS: Rt = 2.21 min, 99 A% 254nm, [M + H]+= 300.8. 1HNMR (600 MHz, DMSO-d6) delta 8.88 – 8.84 (m, 2H), 8.69 (s, 1H),8.06 (s, 1H), 7.44 (t, J = 4.9 Hz, 1H), 4.93 (dd, J = 6.5, 4.4Hz, 2H), 4.80 (dd, J = 6.6, 4.4 Hz, 2H), 1.93 (s, 3H). 13CNMR (150 MHz, DMSO-d6) delta 158.3, 157.8, 151.1,146.5, 138.4, 133.2, 127.3, 120.2, 48.9, 46.0, 12.9. HRMS calcd for C12H12N8NaO2 [M + Na]+, 323.0975; found, 323.0976.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,37972-24-0, 2-Ethynylpyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Jarrad, Angie M.; Karoli, Tomislav; Debnath, Anjan; Tay, Chin Yen; Huang, Johnny X.; Kaeslin, Geraldine; Elliott, Alysha G.; Miyamoto, Yukiko; Ramu, Soumya; Kavanagh, Angela M.; Zuegg, Johannes; Eckmann, Lars; Blaskovich, Mark A.T.; Cooper, Matthew A.; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 96 – 102;,
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Pyrimidine – Wikipedia

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. 51-20-7, name is 5-Bromouracil, the common compound, a new synthetic route is introduced below. Application In Synthesis of 5-Bromouracil

Step 1 . Preparation of 5-[benzyl(methyl)amino]-1 /-/-pyrimidine-2,4-dione 5-Bromouracil (0.15 g, 0.78 mmol) was dispersed in /V-benzylmethylamine (2.0 mL, 15.70 mmol) and heated at 120 C for 1 hr under microwave irradiation. The reaction mixture was diluted with water (1 mL) and concentrated. The white solid obtained was washed with water (10 mL), MeOH (5 mL) and then collected by dispersion in EtOAc (10 mL). The solvent was removed by evaporation to afford the title compound (0.22 g, 86%) as white powder. Analytical data were consistent with those reported in the literature {Tetrahedron2005, 67(12), 3107-31 13). 1H NMR (400 MHz, DMSO-d6): delta 2.42 (s, 3H), 4.07 (s, 2H), 6.62 (s, 1 H), 7.15-7.39 (m, 5H), 10.40 (br s, 1 H), 1 1 .07 (s, 1 H).MS (ESI) m/z: 232 [M-H]+.

The synthetic route of 51-20-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FONDAZIONE ISTITUTO ITALIANO DI TECNOLOGIA; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; UNIVERSITA’ DEGLI STUDI DI PARMA; PIOMELLI, Daniele; REALINI, Natalia; MOR, Marco; PAGLIUCA, Chiara; PIZZIRANI, Daniela; SCARPELLI, Rita; BANDIERA, Tiziano; WO2013/178576; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia