Day: March 25, 2022

Related Products of 890094-38-9 , The common heterocyclic compound, 890094-38-9, name is 2-Chloro-N-isopropyl-5-nitropyrimidin-4-amine, molecular formula is C7H9ClN4O2, 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.

General procedure: The reaction of 2,4-dichloro-5-nitropyrimidine withisopropylamine produced intermediate 2-chloro-N-isopropyl-5-nitropyrimidin-4-amine. 4-Fluoronitrobenzene reacted with1-methylpiperazine in DMSO yielded the intermediate 1-methyl-4-(4-nitrophenyl)piperazine in the presence of K2CO3. The catalytichydrogenation of 1-methyl-4-(4-nitrophenyl)piperazine with palladiumon carbon (Pd/C, 5%) quantificationally provided thedesired 4-(4-methylpiperazin-1-yl) aniline. Refluxing of the 2-chloro-N-isopropyl-5-nitropyrimidin-4-amine with 4-(4-methylpiperazin-1-yl)aniline in n-butanol yielded N4-isopropyl-N2-(4-(4-methylpiperazin-1-yl)phenyl)-5-nitropyrimidine-2,4-diamine,which was reduced to intermediate A1 with a good yield by catalytichydrogenation using Pd/C as a catalyst. Intermediates A wereprepared as these steps and used for the next step without furtherpurification. These processes were carried out as reported

The synthetic route of 890094-38-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hei, Yuan-Yuan; Shen, Ying; Wang, Jin; Zhang, Hao; Zhao, Hong-Yi; Xin, Minhang; Cao, Yong-Xiao; Li, Yan; Zhang, San-Qi; Bioorganic and Medicinal Chemistry; vol. 26; 8; (2018); p. 2173 – 2185;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 3438-61-7, 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. 3438-61-7, name is 5-Amino-4-methylpyrimidine, molecular formula is C5H7N3, 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.

225.0 g (2.06 mol) of 4-methyl-5-aminopyrimidine was dissolved in 10.0 L of anhydrous THF in a dry flask under nitrogen blanket. The solution was cooled to -200C. 2.0 L (1.39 kg, 5.00 mol) of 2.5 M «-BuLi in hexane was added in 20 minutes while the temperature was kept below -50C. The mixture was agitated at below -15C for 30 minutes and then warmed up to normal room temperature (RT) and stirred for 3 hours. 250.0 g (0.61 mol) of the above methyl ester from stage 7, in 250 mL of anhydrous THF, was added over 25 minutes while the temperature was kept below 350C. The light yellow slurry turned to a dark solution. The solution was stirred for 20 minutes. A reaction sample was quenched with MeOH and analyzed by HPLC to make certain that there is no starting methyl ester left. The solution was then cooled back to below 150C. 2.0 L of MeOH was added over 10 minutes while the temperature was kept below 250C followed by 1.0 L of water added in one portion and the mixture was allowed to warm up to room temperature and stir for 15 hours. A reaction sample was analyzed by HPLC to make certain all related intermediates have been converted. The mixture was cooled to below 200C. 1.2 L of 6 N hydrochloric acid was added over 35 minutes while the temperature was kept below 250C. The solution was agitated for 1 hour. The reaction was monitored by HPLC to make certain that all related intermediates had been converted. The solution was cooled to below 150C. 6 N of NaOH was added to adjust the solution pH to 7-8 (about 370 mL was needed). Most solvents (14.5 L) were removed under vacuum (140 mmHg) and 4.0 L of EtOAc and 2.0 L of water were added. Layers were separated and the organic layer was washed with three 2.0 L portions of water and 1.0 L of brine. The solvent was removed under vacuum from the organic layer to yield 450.0 g of a thick dark brown oil as the crude product. The residue was chased with 500 mL of «-propanol to get 393.2 g of a thick slurry. 500 mL of «-propanol was added and the mixture was heated up to 600C to dissolve the solid. The solution was cooled down with agitation and the slurry was filtered after 16 hours at room temperature and the solid was washed with the filtrate and two 100 mL portions of n- propanol and two 200 mL portions of hexane and air dried to yield the title compound (R)- 1,1,1 -trifluoro-4-(5-fluoro-2-methylphenyl)-4-methyl-2-(5H-pyrrolo[3,2-rf]pyrimidin-6- ylmethyl)pentan-2-ol «-propanol solvate as a light yellow solid, 140.2 g, 44% yield.

According to the analysis of related databases, 3438-61-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2009/134737; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 81765-97-1 ,Some common heterocyclic compound, 81765-97-1, molecular formula is C11H11ClN2S, 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 the solution of 4-amino-2-fluorophenol (41 mg, 0.32 mmol) in dried DMF (3 mL), was added NaH (13 mg, 0.54 mmol). The mixture was stirred at 0 °C for 10 min, and then a solution of 4-chloro-5-(4-fluorophenyl)thieno[2,3-d]pyrimidine 4i (50 mg, 0.19 mmol) in dried DMF (1 mL) was added. The mixture was stirred at 0 °C for 1.5 h. Ice water (5 mL) was added to quench the reaction and the mixture was extracted by Et2O (3 .x. 10 mL). The organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure to obtain the crude product, which was purified by silica gel column chromatograph.

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. 81765-97-1, 4-Chloro-2-methyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhao, Ailing; Gao, Xin; Wang, Yuanxiang; Ai, Jing; Wang, Ying; Chen, Yi; Geng, Meiyu; Zhang, Ao; Bioorganic and Medicinal Chemistry; vol. 19; 13; (2011); p. 3906 – 3918;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1801-06-5, 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 1801-06-5, name is 4-Chloro-5-fluoro-2-methoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

The 32.5g formula III compound are added 170g10wt percent of the isopropyl alcohol solution of ammonia, heating to 40-60°C, stirring reaction 3-5 hours, natural cooling to room temperature, filtered, collecting solid, washing with isopropyl alcohol, drying, the compound of formula II is obtained (kind of white solid) 27.2g, molar yield is 95.0percent, HPLC purity of 99.0percent.

According to the analysis of related databases, 1801-06-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Dixinuo Chemical Pharmaceutical Co., Ltd; Shanghai Desano Pharmaceutical Co., Ltd.; Li, Jinliang; Zhao, Nan; Hua, Sikai; (6 pag.)CN105272922; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 66522-06-3, 4-(tert-Butyl)-2-chloropyrimidine, 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, HPLC of Formula: C8H11ClN2, blongs to pyrimidines compound. HPLC of Formula: C8H11ClN2

To a solution of Intermediate 3 (5 mg, 0.014 mmol) in n-BuOH (0.5 mL) was added 4-(tert-butyl)-2-chloropyrimidine (4 mg, 0.021 mmol) and iPr2NEt (5 pL, 0.028 mmol) at RT. The mixture was heated in a microwave reactor at 180 C for 90 min, then was cooled to RT. To the reaction mixture was added THF (0.8 mL)/H20 (0.4 mL)/MeOH (0.4 mL) and LiOH.H20 (3 mg, 0.070 mmol), and the mixture was stirred at RT overnight. Volatiles were removed in vacuo and the residue was diluted with H20 (5 mL), and then the mixture was adjusted with 1N aq. HC1 to pH ~5 and extracted with EtOAc (3 x 5 mL). The combined organic extracts were washed with brine (2 mL), dried (MgSCL) and concentrated in vacuo. The crude product was purified by preparative LC/MS (Column: Waters XBridge Cl 8, 19 x 200 mm, 5-pm particles; Guard Column: Waters XBridge C18, 19 x 10 mm, 5-pm particles; Mobile Phase A: 5:95 MeCN:H20 with 0.1% TFA; Mobile Phase B: 95:5 MeCN:H20 with 0.1% TFA; Gradient: 50-90% B over 20 min, then a 5 min hold at 100% B; Flow: 20 mL/min) to provide the title compound (5.3 mg, 10.7 pmol, 77 % yield). LCMS, [M + H]+ = 480.1. NMR (500 MHz, DMSO-de) d 8.18 (d, ,7=4.3 Hz, 1H), 7.82 (d, ,7=8.5 Hz, 1H), 7.49 (d, J=92 Hz, 2H), 6.62 (d, ,7=4.6 Hz, 1H), 4.97 (br. s., 2H), 4.79 – 4.72 (m, 1H), 4.10 (s, 3H), 2.60 – 2.53 (m, 3H), 2.43 (s, 3H), 2.00 – 1.43 (m, 10H), 1.08 (br. s., 9H). hLPAi IC5o = 26 nM.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,66522-06-3, 4-(tert-Butyl)-2-chloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHI, Yan; WANG, Ying; CHENG, Peter Tai Wah; SHI, Jun; TAO, Shiwei; CORTE, James R.; FANG, Tianan; LI, Jun; KENNEDY, Lawrence J.; KALTENBACH, III, Robert F.; JUSUF, Sutjano; (316 pag.)WO2019/126093; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 87026-45-7, 4-Chloro-5-methoxy-2-(methylthio)pyrimidine, 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-methoxy-2-(methylthio)pyrimidine, blongs to pyrimidines compound. Safety of 4-Chloro-5-methoxy-2-(methylthio)pyrimidine

A round bottom flask containing ethyl formate (6 mL, 0.062 mol) and ethyl ether (30 mL) was placed in an ice water bath, Na (1.4 g, 0.062 mol) was added under stirring, and then methyl 2-methoxyacetate (6.5 g, 0.062 mol) was added dropwise. The mixture was stirred at room temperaturefor 4 h. The reaction was quenched by addition of ice water (25 mL), and the aqueous phase was separated. To the water layer, S-methyl isothiourea (5.6 g, 0.062 mol) and KOH (2.2 g, 0.062 mol) were added within 40 min, and then heated to 65 C for 1 h. After cooling, the reaction mixture was neutralized with 37% HCl. The crude product was collected by vacuum filtration, and then recrystallized with 95% ethanol to afford 2 as a white needle crystal (4.3 g, 40.1% yield). m.p. 193-195 C.The intermediate 2 (1.7 g, 0.01 mol) was added slowly into POCl3 (4.6 g, 0.03 mol) in ice-water bath, and then the mixture was heated to 80 C for 1 h until the reaction was completed. The reaction mixture was cooled to room temperature and neutralized with 25% ammonia water. The precipitated solid was filtered and recrystallized with petroleum ether, decolorized by activated carbon. The intermediate 3 was obtained as a light yellow solid (1.8 g, 95.2% yield). m.p. 74-75 C. The intermediate 3 was dissolved in methanol (10 mL), 50% hydrated hydrazine solution (1.6 g, 0.015 mol) was added dropwise in an ice-water bath. Then the mixture was heated to 50 C and monitored by TLC until the reaction was finished. After cooling, the solvent was removed under reduced pressure, and the solid was recrystallized from ethyl acetate and petroleum ether to afford 5-methoxy-2-(methylthio) pyrimidin-4-yl hydrazine (4, 1.1 g, 96.2%yield). m.p. 112-114 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,87026-45-7, 4-Chloro-5-methoxy-2-(methylthio)pyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Song, Gaopeng; Li, Jianzuo; Tian, Hao; Li, Yasheng; Hu, Dekun; Li, Ying; Cui, Zining; Letters in drug design and discovery; vol. 13; 4; (2016); p. 329 – 334;,
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.147539-23-9, name is 1-Boc-4-(6-Chloro-5-nitro-4-pyrimidinyl)piperazine, molecular formula is C13H18ClN5O4, molecular weight is 343.77, as common compound, the synthetic route is as follows.category: pyrimidines

PREPARATION 10 1-[1,1-Dimethylethoxycarbonyl]-4-[5-amino-6-pyrimidinyl]piperazine A mixture of 1-[1,1-dimethylethoxycarbonyl]-4-[4-chloro-5-nitro-6-pyrimidyl]piperazine and triethylamine (0.3 ml) and palladium on carbon (5%, 0.13 g) in ethanol (100 ml) is charged with hydrogen gas (30 psi). After the theoretical amount of hydrogen gas is consumed, the catalyst is removed under reduced pressure. The filtrate is concentrated under reduced pressure to a foam which is diluted with an aqueous saturated solution of potassium carbonate and dichloromethane. The phases are separated and the organic phase is dried over sodium sulfate and concentrated to give to give the title compound, NMR (CDCl3) 1.49, 3.49, 3.29, 3.56, 7.98, and 8.39 delta.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,147539-23-9, 1-Boc-4-(6-Chloro-5-nitro-4-pyrimidinyl)piperazine, and friends who are interested can also refer to it.

Reference:
Patent; The Upjohn Company; US5599930; (1997); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 53557-69-0, name is 6-Iodopyrimidin-4-amine. A new synthetic method of this compound is introduced below., COA of Formula: C4H4IN3

Step 2: 5-(6-Aminopyrimidin -yl)-2-(5-chloro-2-ethylphenyl)-1-(phenylsulfonyl)-1 H^yrrole-3-carbon (VI) 2-(5-Chloro-2-ethylphenyl)-1-(phenylsulfonyl)-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 – -pyrrole-3-carbonitrile (2.77 mmol), 6-iodopyrimidin-4-amine (918 mg, 4.16 mmol), PdCI2(dppf) (226 mg, 0.277 mmol) and Cs2C03(2.71 g, 8.31 mmol) were degassed and back filled with argon and then dissolved in dioxane (20 mL) and water (4 mL) under nitrogen. The reaction mixture was stirred at room temperature over night, then diluted with EtOAc, washed with aqueous brine, dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by Biotage SP1 Flash Chromatography (DCM/MeOH/NH37 N in MeOH 95/5/0.5) to afford the title compound (540 mg, 39%, 2 steps).1H NMR (600 MHz, DMSO-d6) delta 8.45 (d, J = 0.92 Hz, 1 H), 7.82 (t, J = 7.42 Hz, 1 H), 7.71 – 7.78 (m, 1 H), 7.59 – 7.63 (m, 1 H), 7.56 (dd, J = 2.29, 8.33 Hz, 1 H), 7.39 (d, J = 8.43 Hz, 1 H), 7.11 (br. s., 1 H), 7.09 (s, 1 H), 6.83 (d, J = 2.20 Hz, 1 H), 6.64 (d, J = 1.10 Hz, 1 H), 2.03 – 2.24 (m, 2H), 1.01 (t, J = 7.60 Hz, 3H).HRMS (ESI) m/z calcd for C23H18N502SCI + H+464.0943, found 464.0938.

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, 53557-69-0, 6-Iodopyrimidin-4-amine.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; BRASCA, Maria Gabriella; BINDI, Simona; CALDARELLI, Marina; NESI, Marcella; ORRENIUS, Sten Christian; PANZERI, Achille; WO2014/19908; (2014); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 76044-36-5, 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. 76044-36-5, name is 5-Chloro-[1,2,4]triazolo[1,5-c]pyrimidine, molecular formula is C5H3ClN4, 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.

To a solution of 5-choro-[I,2,4]triazoo[l,5-c]pyrimidine (120 mg, 776 mhio) in DMA (3.88 mL) was added (35,4;S)-3-methyl~2-oxa~8~azaspiro[4.5]decan-4-amine his hydrochloride (277 mg, 1.16 mmol) and DIPEA (675 m]_, 3.88 mmol). The reaction mixture was stirred in a capped vial at 90 C for 1 h. The resulting mixture was concentrated under reduced pressure and the crude residue was carried onto the next step without any further purification. LCMS (ESI): m/z: [M + H] calculated for C ui fuNA). 289.2; found 289.3.

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 76044-36-5, 5-Chloro-[1,2,4]triazolo[1,5-c]pyrimidine.

Reference:
Patent; REVOLUTION MEDICINES, INC.; KOLTUN, Elena S.; AAY, Naing N.; BUCKL, Andreas; MELLEM, Kevin T.; BLANK, Brian R.; PITZEN, Jennifer; WANG, Gang; JOGALEKAR, Ashutosh S.; WON, Walter S.; TZITZILONIS, Christos; LI, Jie Jack; GILL, Adrian Liam; CREGG, James Joseph; (207 pag.)WO2019/118909; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 499195-60-7, 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.499195-60-7, name is Ethyl 4-(2-chloropyrimidin-4-yl)benzoate, molecular formula is C13H11ClN2O2, molecular weight is 262.69, as common compound, the synthetic route is as follows.

Step 1 : Preperation of ethyl 4-(2-((4-(4-(2-oxopyrrolidin-l-yl)piperidin-l-yl) phenyl) amino) pyrimidin-4-yl)benzoate. To a solution of ethyl 4-(2-chloropyrimidin-4-yl)benzoate (7.09 g, 27.0 mmol), in isopropyl alcohol [100 mL] was added l-(l-(4-aminophenyl)piperidin-4- yl)pyrrolidin-2-one (7.0 g, 27.0 mmol). To this, trifluoro acetic acid (4.62 g, 40.0 mmol) was added and mixture was heated at 120 C in sealed tube for 16 h. After completion of reaction, mixture was quenched in water, basified with ammonia solution and extracted with ethyl acetate. Organic layer was washed with water, dried over sodium sulfate and removed under reduced pressure to give crude off white solid compound. Purification of crude product was done by the way of column chromatography (Si02, hexane to 30 % EtOAc in hexane) to get solid compound (10.7 g, 82%). The title compound was characterized by spectral analysis. ESI-MS: 486.2 (M+H)+.

Statistics shows that 499195-60-7 is playing an increasingly important role. we look forward to future research findings about Ethyl 4-(2-chloropyrimidin-4-yl)benzoate.

Reference:
Patent; CADILA HEALTHCARE LIMITED; DESAI, Ranjit, C.; DESAI, Jigar; PATEL, Pankaj; WO2015/19365; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia