Tag: M.W=300-400

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. 761440-16-8, name is 2,5-Dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C13H13Cl2N3O2S

To a solution of 7 (200 mg, 0.979 mmol) in 0.08 M HCl inethoxyethanol (1.0 mL) and 2,5-dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine (4, 407 mg, 1.17 mmol) was added at rtand the reaction mixture was stirred at 80 C for 12 h. The solidprecipitated was filtered and washed with ethanol (2 mL). The solidfiltered was then dissolved in EtOAc (50 mL) and washed with sat.NaHCO3 (aq). The combined organic layers were concentrated underreduced pressure to obtain the crude product which was purifiedby silica gel column chromatography using MeOH/DCM (1:9)to afford the title compound (433 mg, 0.875 mmol, 94%) as a whitesolid. Mp 207.4-209.6 C; 1H NMR (300 MHz, CDCl3) delta 9.53 (s, 1H),8.53 (d, J= 8.3 Hz, 1H), 8.18 (s, 1H), 8.12 (s, 1H), 7.94 (dd, J = 7.9,1.3 Hz, 1H), 7.66 (t, J = 7.3 Hz, 1H), 7.53 (s, 1H), 7.30 (t, J = 7.9 Hz, 1H),6.83 (s, 1H), 3.90 (s, 3H), 3.26 (sept, J = 6.9 Hz, 1H), 2.45 (s, 3H), 1.79(s, 6H), 1.32 (d, J = 6.9 Hz, 6H); 13C NMR (125 MHz, CDCl3) delta 157.32,155.40, 155.33, 146.15, 138.34, 134.76, 131.36, 131.11, 128.33, 125.00,124.58, 123.55, 123.38, 122.45, 107.24, 106.48, 55.93, 55.52, 35.00,28.27, 20.78, 15.37; LC/MS m/z 513.8 [M+H+]; HRMS (EI) m/z calcdfor C25H28ClN5O3S [M+] 513.1601, found 513.1607.

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, 761440-16-8, 2,5-Dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine.

Reference:
Article; Mathi, Gangadhar Rao; Kang, Chung Hyo; Lee, Heung Kyoung; Achary, Raghavendra; Lee, Ha-Yeon; Lee, Joo-Youn; Ha, Jae Du; Ahn, Sunjoo; Park, Chi Hoon; Lee, Chong Ock; Hwang, Jong Yeon; Yun, Chang-Soo; Jung, Hee Jung; Cho, Sung Yun; Kim, Hyoung Rae; Kim, Pilho; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 536 – 549;,
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Reference of 330785-81-4, 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.330785-81-4, name is Ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-carboxylate, molecular formula is C16H18ClN3O3S, molecular weight is 367.85, as common compound, the synthetic route is as follows.

The product VI obtained in the step (1) is added to 450 ml of ethanol, heated and stirred at 50-55 C until the temperature of the material is cooled to 20-30 C, 105 ml of 10% sodium hydroxide solution is added and stirred at 20-30 C for 1.5-2 hours. The mixture was added dropwise with 10% citric acid solution to adjust the pH of the solution to about 4 ~ 5. A large amount of solid was precipitated and the mixture was stirred at 20-30 C for 1-1.5h. The solid was washed with water and dried under vacuum at 50 C for 3h to obtain 14.0g of white solid. Yield 93.3%.

The chemical industry reduces the impact on the environment during synthesis 330785-81-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Guangzhou Langsheng Pharmaceutical Co., Ltd.; Chen Yuhua; Lu Pingping; Mo Enqing; Zuo Lian; Lu Zhijun; Peng Guizi; Yuan Yongling; (14 pag.)CN104059025; (2017); B;,
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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. 428854-24-4, name is 2-(1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidine-4,5,6-triamine, the common compound, a new synthetic route is introduced below. Quality Control of 2-(1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidine-4,5,6-triamine

n three flask, pyridine (5mL), was added compound 7 (350mg, 1mmol, 1.0eq), stirred for 20 minutes in an ice bath, was added methyl chloroformate (162mg, 1.5mmol, 1.5eq), continued in an ice bath the mixture was stirred for 1 hour. Warmed to room temperature and stirring was continued for 2 hours. After completion of the reaction, concentrated under reduced pressure, the residue was dissolved in ethanol, and then concentrated under reduced pressure was repeated twice to give a yellow solid (390 mg of), a yield of 95.7%.

The synthetic route of 428854-24-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Okuura Dayton (Shanghai) Pharmaceutical Co., Ltd; Shanghai Pharmaceutical Group Co., Ltd; Yu, Libing; Guo, Maojun; Yang, Qingang; Ji, Zhangyou; (16 pag.)CN105777743; (2016); A;,
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Application of 1421372-94-2 ,Some common heterocyclic compound, 1421372-94-2, molecular formula is C20H16FN5O3, 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 N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(l- methyl-1 H-indol-3 -yl)pyrimidin-2-amine (200 mg, 0.508 mmol) and diisopropylethylamine (0.328 mg, 2.54 mmol) in dimethyl sulfoxide (4 mL) was added 3-((dimethylamino)methyl)- N-methylbicyclo[l . l. l]pentan-l-amine (117 mg, 0.762 mmol). The mixture was heated at 100 “C for 24 h. The mixture was cooled to RT and diluted with dichloromethane and water. The organic layer was separated, dried over Na2S04 and concentrated in vacuo. The crude product was purified by HPLC (10:90 to 80:20 0.1% HC02H (aq):MeCN) to afford Nl-(3- ((dimethylamino)methyl)bicyclo[ 1.1.1 Jpentan- 1 -yl)-5-methoxy-Nl -methyl-N4-(4-(l -methyl- lH-indol-3-yl)pyrimidin-2-yl)-2-nitrobenzene-l,4-diamine (140 mg, 52%). LC/MS (ESI) m/z 528.6 [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. 1421372-94-2, N-(4-Fluoro-2-methoxy-5-nitrophenyl)-4-(1-methyl-1H-indol-3-yl)pyrimidin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KALYRA PHARMACEUTICALS, INC.; BUNKER, Kevin, Duane; HUANG, Peter, Qinhua; ABRAHAM, Sunny; PINCHMAN, Joseph, Robert; HOPKINS, Chad, Daniel; SLEE, Deborah, Helen; (93 pag.)WO2017/205459; (2017); A1;,
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Synthetic Route of 428854-24-4, 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.428854-24-4, name is 2-(1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidine-4,5,6-triamine, molecular formula is C17H15FN8, molecular weight is 350.35, as common compound, the synthetic route is as follows.

Step three, A solution of formic acid (129 g, 1.37 mol)Was added dropwise to acetic anhydride (145 g, 1.42 mol)After stirring for half an hour, compound 4 (80 g, 0.23mo 1) was added at 0 C, stirred at 20 C for 10 hours,TLC detection reaction is completed, concentrated reaction solution, add 500mL of water for half an hour, pumping,Dried to give about 78 g of a yellow solid which was dissolved in 500 mL of tetrahydrofiramidate and sodium borohydride (15.58 g, 0.41 mol) was added at room temperature. A solution of boron trifluoride diethyl ether (90 mL) was slowly added dropwise at room temperature, Slowly heated to reflux for 3 hours. After the reaction, add 120mL methanol to destroy, then add 2N hydrochloric acid 120mL, stir for half an hour after the reaction system, the residue with 2N sodium hydroxide solution to adjust the pH to neutral, and then suction, Drying to obtain a crude product of compound 5a,The crude product of compound 5a was dissolved in a mixed solvent of dichloromethane and methanol (the weight ratio of the crude product of compound 5a to 1: 5, the volume ratio of dichloromethane to methanol in the mixed solvent was 1: 15) ,And the mixture was stirred at room temperature for 10 hours and then filtered and dried to obtain pure product (63.7 g, 0.17 mol, yield: 76%, content: 99%) /

The chemical industry reduces the impact on the environment during synthesis 428854-24-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Anhui Lianchuang Biological Medicine Co.,Ltd; GE, DEPEI; WU, QIHUA; LIU, TAO; (10 pag.)CN104530044; (2016); B;,
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Electric Literature of 131860-97-4, 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. 131860-97-4, name is (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate. A new synthetic method of this compound is introduced below.

Methyl (£)-2-{2-[6-chloropyiimidin-4-yloxy]phenyl}-3-methoxyacrylate (E) (3g of 95.4% strength) was charged to the reaction tube followed by the solvent (10 ml) then 2- cyanophenol (1.2g), base (1.5 mol equivalents) and the compound being tested as a catalyst (15 mol%). The reaction mixtures were held, with stirring, at 400C for 4hrs, then at 6O0C for 2 hrs. The reaction was monitored for formation of product, throughout the hold period, by Gas Chromatography. Results are recorded as area % levels of methyl (£)-2-{2-[6- chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (II) and methyl (E)-2-{2-[6-(2- cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (I) in the reaction mixture.The following systems were tested:TABLE l The results are shown in Table 2 below:TABLE 2

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,131860-97-4, its application will become more common.

Reference:
Patent; SYNGENTA LIMITED; WO2008/43977; (2008); A1;,
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Reference of 131860-97-4, 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.131860-97-4, name is (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, molecular formula is C15H13ClN2O4, molecular weight is 320.73, as common compound, the synthetic route is as follows.

Methyl (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylate (97.6 gm), 2-cyanophenol (36.9 gm), and potassium carbonate (25.4 gm) are added to, mixed, and dissolved in an aprotic solvent (241 gm) at room temperature. In this embodiment, the aprotic solvent is, for example, toluene. Then, 1-methylpyrrolidine (10.2 gm, 0.4 eq) is added as a catalyst, and stirred until uniform to form a basic mixture. Subsequently, the basic mixture is heated to 80 C., and reacted for 3 hrs. (0019) The basic mixture after reaction is subjected to a first distillation under a reduced pressure of 100 torr at 80 C., and the product left after the first distillation under reduced pressure is azoxystrobin. The distillate by the first distillation under reduced pressure is detected by gas chromatography (GC), and 1-methylpyrrolidine is determined to have a recovery rate of 96.3%. (0020) Azoxystrobin left after the first distillation under reduced pressure is added to the aprotic solvent (241 gm) and water (114 gm), mixed, and stirred until azoxystrobin is completely dissolved. After standing for layer separation, an upper first organic layer is collected, and then a lower aqueous layer is collected and further added with the aprotic solvent (15 gm). Next, an upper second organic layer is collected. The first organic layer and the second organic layer are combined, and detected by high performance liquid chromatography (HPLC) to show a yield of azoxystrobin of 94.9%. The combined organic layer is subjected to a second distillation under reduced pressure at 50-60 C. under 20-40 torr, to remove the solvent. This gives a crude product. The crude product is dissolved in methanol (156 gm) at 60 C., cooled to normal temperature and then to 5 C., and filtered to obtain a crystalline solid. The crystalline solid was washed with methanol (13 gm) and then dried at 50 C., to obtain purified azoxystrobin (112.9 gm) as a solid (yield 91.5%).

Statistics shows that 131860-97-4 is playing an increasingly important role. we look forward to future research findings about (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate.

Reference:
Patent; SINON CORPORATION; CHEN, Chien-Hsing; HSIEH, Ming-Fang; LIN, Chih-Da; LIU, Chien-Yu; (4 pag.)US2020/165210; (2020); A1;,
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Synthetic Route of 302964-08-5 ,Some common heterocyclic compound, 302964-08-5, molecular formula is C16H13Cl2N5OS, 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 34; Procedure for the Preparation of Dasatinib Form N2A mixture of compound 1 (1.5 mmol), N-(2-hydroxyethyl)piperazine (3 mmol) and N-ethyldiisopropylamine (3 mmol) was heated in DMSO (1.3 ml) at 80-85 C. for 1.5 hours. n-Butanol (7.0 ml) was slowly added at this temperature. The suspension was slowly cooled to 0-5 C. Product was filtered off and washed with n-butanol (10.0 ml) and dried on the filter.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,302964-08-5, its application will become more common.

Reference:
Patent; SIMO, Ondrej; Filipcik, Jiri; Martaus, Alexandr; Jegorov, Alexandr; Gavenda, Ales; Aronhime, Judith; Vraspir, Pavel; Koltai, Tamas; Faustmann, Jiri; Gabriel, Roman; US2009/118297; (2009); 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. 302964-08-5, name is 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, the common compound, a new synthetic route is introduced below. HPLC of Formula: C16H13Cl2N5OS

Example 32; Procedure for the Preparation of Dasatinib Form L1A mixture of compound 1 (1.5 mmol), N-(2-hydroxyethyl)piperazine (3 mmol) and N-ethyldiisopropylamine (3 mmol) in DMF was stirred at 100 C. for 4 h, 2-butanole was added at this temperature. The suspension was slowly cooled to 0-5 C. The product was filtered off, washed by 2-butanol and dried on the filter.

The synthetic route of 302964-08-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIMO, Ondrej; Filipcik, Jiri; Martaus, Alexandr; Jegorov, Alexandr; Gavenda, Ales; Aronhime, Judith; Vraspir, Pavel; Koltai, Tamas; Faustmann, Jiri; Gabriel, Roman; US2009/118297; (2009); A1;,
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Synthetic Route of 147118-37-4 , The common heterocyclic compound, 147118-37-4, name is N-(4-(4-Fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide, molecular formula is C16H18FN3O3S, 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 10: Preparation of Methyl 7-[4-(4-flouropheny.)-6-isopropyl-2-(N-methyl- N-methylsulfonylamino)-pyrimidin-5-yl] – (3R)-3hydroxy-5-oxo-(E)-6-heptenate (Rosuvastatin intermediate)A solution of 25 g 4-(4-flourophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonyl amino)-5-pyrimidine carbaldehyde, 55 g Methyl (3R)-3-(t-butyldimethylsilyloxy)-5-oxo- 6-triphenyl phosphoranylidene hexanoate and acetonitrile was refluxed for about 20 hrs. The reaction mass was concentrated under vacuum. To this cyclohexane was added. The reaction mass was stirred and filtered. Filtrate was Concentrated under u/v and taken into acetonitrile, cooled to 0 C. To this solution of hydrogen fluoride (100 ml) was added drop wise in acetonitrile under ice cooling, and the mixture was warmed to room temperature and stirred for 1-3 hrs. To this a mixture of DM water and dichloromethane was added and neutralized with sodium bicarbonate solution. The reaction mixture was stirred and layers were separated. The organic layer was washed with water and brine solution. To the concentrated IPA was added, stirred, and filtered. The obtained solid was washed IPE and dried to give Methyl 7-[4-(4-flourophenyl)-6-isopropyl-2-(N-methyl-N- methylsulfonylamino)-pyrimidin-5-yl] – (3R)-3-hydroxy-5-oxo-(E)-6-heptenate(32 g).

The synthetic route of 147118-37-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MATRIX LABORATORIES LTD.; SETHI, Madhuresh, Kumar; MAHAJAN, Sanjay; RAWAT, Vijendra, Singh; MARA, Bhairaiah; VEERA, Upendra, Nath; DATTA, Debashish; WO2011/141934; (2011); A1;,
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