Day: September 7, 2021

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.761440-16-8, name is 2,5-Dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine, molecular formula is C13H13Cl2N3O2S, molecular weight is 346.23, as common compound, the synthetic route is as follows.HPLC of Formula: C13H13Cl2N3O2S

2,5-dichloro-N-(2-(isopropylsulfonyl)phenyl)py-rimidine-4-amine (472 mg, i.36 mmol) was dissolved in 0.08 M HC1-ethoxyethanol (i .0 mE), to which the compound (200 mg, 0.979 mmol) prepared in preparative example 2i was added, followed by stirring at 80 C. for i2 hours. The reaction mixture was cooled to room temperature, neutralized with sodium hydrogen carbonate aqueous solution, and extracted twice with ethylacetate. The extracted organic layer was dried over sodium sulfate and then filtered. The solvent was eliminated by distillation under reduced pressure. Then, purification was performed by silica gel column chromatography (eluent: methanol dichloromethane, 1/9) to give the target compound 2-(4-((5- chioro-4-((2-(isopropylsulfonyl)phenyl)amino)pyrimidine- 2-yl)amino)-5-methoxy-2-methylphenyl)-2- methylpropanenitrile as a white solid (433 mg, 0.875 mmol, yield: 86%).10584] ?H-NMR (300 MHz, CDC13) oe 9.53 (s, br, 1H),8.52 (d, J=8.3 Hz, 1H), 8.18 (s, 1H), 8.12 (s, 1H), 7.94 (d,J=7.9 Hz, 1H), 7.66 (t, J=7.3 Hz, 1H), 7.53 (s, br, 1H), 7.28(t, J=7.8 Hz, 1H), 6.83 (s, 1H), 3.90 (s, 3H), 3.26 (sept, J=6.9Hz, 1H), 2.44 (s, 3H), 1.79 (s, 6H), 1.32 (d, J=6.9 Hz, 6H);LC/MS 513.8 [M+H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,761440-16-8, 2,5-Dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; Kim, Pilho; Kim, Hyoung Rae; Cho, Sung Yun; Ha, Jae Du; Jung, Hee Jung; Yun, Chang Soo; Hwang, Jong Yeon; Park, Chi Hoon; Lee, Chong Ock; Ahn, Sunjoo; Chae, Chong Hak; (97 pag.)US2018/111905; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 3438-46-8, Adding some certain compound to certain chemical reactions, such as: 3438-46-8, name is 4-Methylpyrimidine,molecular formula is C5H6N2, 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 3438-46-8.

To A SUSPENSION OF NAH (2. 26 G 50%, 47. 7 MMOL) IN DMF (92 ML) UNDER ARGON atmosphere and cooled to 0 C, 4-METHYLPYRIMIDINE (3. 00 G, 31. 9 MMOL) WAS added SLOWLY. THEN, ETHYL 4-FLUOROBENZOATE (6. 40 G, 38. 2 MMOL) WAS ADDED AND IT was stirred at room temperature overnight. Water was added and the solvent was evaporated. The residue was taken up in A mixture of ETOAC and brine. The phases were separated and the aqueous phase was REEXTRACTED with ETOAC. The combined organic PHASES WERE DRIED OVER NA2S04 AND CONCENTRATED TO DRYNESS. The crude PRODUCT OBTAINED BY CHROMATOGRAPHY ON SILICA GEL USING HEXANE-ETOAC mixtures OF INCREASING POLARITY AS ELUENT, TO AFFORD 3. 30 G OF THE DESIRED COMPOUND (YIELD : 48%). H NMR (300 MHZ, CDCI3) 8 (TMS) : 4. 11 (KETONE : S, 2 H), 5. 94 (ENOL : S, 1 H), 6. 94 (ENOL : D, J = 5. 4 HZ, 1 H), 7. 08-7. 16 (M, 2 H), 7. 37 (KETONE : D, J = 5. 1 HZ, 1 H), 7. 89 (ENOL : M, 2 H), 8. 08 (KETONE : M, 2 H), 8. 42 (ENOL : D, J = 5. 4 HZ, 1 H), 8. 69 (KETONE : D, J = 5. 1 HZ, 1 H), 8. 81 (ENOL : S, 1 H), 9. 17 (KETONE : S, 1 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. 3438-46-8, 4-Methylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; J. URIACH Y COMPANIA S.A.; WO2004/76450; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 213265-83-9, 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 213265-83-9, name is 4,6-Dichloro-5-fluoropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 4,6-dichloro-5-fluoro-pyrimidine (1.67 g, 10.0 mmol), «-butanol (6 mL) and 28% ammonium hydroxide (12 mL) in a sealed tube was heated at 90 C for 2 hours. The precipitated white crystals were collected by filtration to give the desired compound (1.31 g, 89% yield). LCMS (ESI) m/z: 147.9 [M+H+].

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 213265-83-9, 4,6-Dichloro-5-fluoropyrimidine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLENCH, Toby; ELLWOOD, Charles; GOODACRE, Simon; LAI, Yingjie; LIANG, Jun; MACLEOD, Calum; MAGNUSON, Steven; TSUI, Vickie; WILLIAMS, Karen; ZHANG, Birong; WO2012/35039; (2012); A1;,
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.24391-41-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile, molecular formula is C7H3ClN4, molecular weight is 178.58, as common compound, the synthetic route is as follows.name: 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

A reaction mixture of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (24.61 mg; 0.14 mmol; 1.02 eq.), cis-4-[1 -(2-azetidin-1 -yl-ethyl)-4-(4-fluoro-3-trifluoromethyl-phenyl)-1 H- imidazol-2-yl]-3-fluoro-piperidine (56.00 mg; 0.14 mmol; 1 .00 eq.), and ethyldiisopropylamine (22.70 mg; 0.18 mmol; 1 .30 eq.) in ACN (1 ml) was stirred at 50C for 36 hr. After cooling to rt, the precipate was collected by filtration to yield the title compound as a yellow solid. LC-MS (M+H = 557, obsd. = 557).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,24391-41-1, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; MERCK PATENT GMBH; LAN, Ruoxi; CHEN, Xiaoling; XIAO, Yufang; HUCK, Bayard R.; GOUTOPOULOS, Andreas; WO2014/143612; (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. 31169-25-2, name is 7-Bromothieno[3,2-d]pyrimidin-4(3H)-one. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H3BrN2OS

7-Bromo-4-chloro-thieno[3,2-d]pyrimidine (192): A solution of 7-bromo-3H-thieno[3,2-d]pyrimid-4-one (191, 153.0 mg, 0.66 mmol) in phosphorus oxychloride (2 mL) was refluxed under N2 for 2 hours. The resulting solution was allowed to cool to room temperature and then neutralized by carefully pouring into a saturated aqueous solution of sodium carbonate. The aqueous mixture was extracted with ethyl acetate and the organic layer washed with water and brine, before drying over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue dried over P2O5 under vacuum overnight (156.0 mg, 95percent yield, white solid).

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, 31169-25-2, 7-Bromothieno[3,2-d]pyrimidin-4(3H)-one.

Reference:
Patent; Thrash, Thomas; Cabell, Larry A.; Lohse, Daniel; Budde, Raymond J.A.; US2006/4002; (2006); 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. 60025-09-4, name is 4-Amino-6-chloropyrimidine-5-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 60025-09-4

General procedure: To a solution of 7a (80mg, 0.18mmol, 1 equiv), 4-amino-6-chloropyrimidine-5-carbonitrile (31mg, 0.2mmol, 1.1 equiv) in BuOH was added DIPEA (0.06mL, 0.36mmol, 2 equiv). The mixture was reacted under microwave at 130C for 20min. After completion, the solvent was removed under reduced pressure. The residue was redissolved in CH2Cl2. The crude was further purified via silica gel chromatography to give compound 8a as white solid (81mg, 80%).

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, 60025-09-4, 4-Amino-6-chloropyrimidine-5-carbonitrile.

Reference:
Article; Wei, Manman; Zhang, Xi; Wang, Xiang; Song, Zilan; Ding, Jian; Meng, Ling-Hua; Zhang, Ao; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 1156 – 1171;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1337532-51-0, 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 1337532-51-0, name is 5-Bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 5-bromo-2-(3,5-dimethylbenzyl)-2H-indazole (0.5 g, 1 .60mmol, 1 equiv) in 1 ,4-dioxane (15 mL) was added bis(pinacolato)diboron (0.4 g, 1 .60mmol, 1 equiv), and potassium acetate (0.47 g, 4.80mmol, 3 equiv) and the mixture was degassed for 15 minutes with argon. PdCl2(dppf)-CH2Cl2 adduct (0.065 g, 0.08mmol, 0.05 equiv) was added and the reaction was heated to 100 C for 5h and the consumption of the starting material was monitored by LCMS. The reaction mixture was cooled to room temperature. 5-bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.363 g, 1 .60mmol, 1 equiv) and saturated aqueous NaHC03 (5 mL) were added, and the mixture was degassed for 15 minutes. PdCI2(dppf)-CH2Cl2 adduct (0.065 g, 0.08mmol, 0. 05 equiv) was added, and the reaction mixture was stirred overnight at 100 C. The mixture was filtered through celite and the filtrate was dried over Na2S04 filtered and concentrated to give crude product. The crude product was purified by flash column chromatography (Silicagel pack) using 3 – 4 % MeOH in DCM mobile phase. The product was further purified by preparative HPLC. Prep HPLC condition: Column: Inertsil ODS 3V( 250 mm X4.6 mm X 5 mic) , Mobile Phase (A)/(B): 0.01 % Ammonia in water : Acetonitrile, Flow rate: 1 mL/min. The fractions containing the desired product were combined and concentrated. The product was basified and extracted with DCM and concentrted to afford the desired product 5-(2-(3,5- dimethylbenzyl)-4-fluoro-2H-indazol-5-yl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.055 g, 9 %) as an off white solid. LCMS (ES) m/z = 383.2 [M+H]+. NMR (400 MHz, DMSO-c/6) delta ppm 2.23 (s, 6H), 3.73 (s, 3 H), 5.54 ( s, 2H), 6.01 (br.s, 2 H), 6.93 (s, 1 H), 6.98 (s, 2H),7.27 (s,1 H), 7.34 – 7.31 (m, 1 H), 7.68 (d, J = 10 Hz, 2 H), 8.13 (s, 1 H), 8.46 (s, 1 H).HPLC: 99.94 % of purity by HPLC254nM

According to the analysis of related databases, 1337532-51-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; AXTEN, Jeffrey Michael; KRISTAM, Rajendra; VENKATESHAPPA, Chandregowda; (105 pag.)WO2019/21208; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 18592-13-7, Adding some certain compound to certain chemical reactions, such as: 18592-13-7, name is 6-(Chloromethyl)pyrimidine-2,4(1H,3H)-dione,molecular formula is C5H5ClN2O2, 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 18592-13-7.

Step 1: Preparation of 5-Bromo-6-(Chloromethyl)uracil (1) To a solution of 6-(chloromethyl)uracil (2.0 g, 12.5 mmol) in DMF (15 mL) at 0 C. was added NBS (recrystallized, 2.44 g, 13.7 mmol). The mixture was stirred at 0 C. for 1.5 h, and then quenched by ice water. The precipitate was collected by filtration and washed with AcOH and water to give the title compound (2.35 g, 69%) as a white solid. 1H NMR (DMSO, 500 MHz) delta 1.66 (s, 1H), delta 11.61 (s, 1H), delta 4.47 (s, 2H). MS (Multimode, M+H+) C5H5BrClN2O2, calcd. 238.9. found 238.9.

According to the analysis of related databases, 18592-13-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cystic Fibrosis Foundation Therapeutics, Inc.; US8334292; (2012); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 49844-90-8, 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.49844-90-8, name is 4-Chloro-2-(methylthio)pyrimidine, molecular formula is C5H5ClN2S, molecular weight is 160.63, as common compound, the synthetic route is as follows.

4-Chloro-2-methylthiopyrimidine (5 g, 31. 15 mmol) was added dropwise to a cooled 57% aqueous hydriodic acid solution (0C). Stirring was continued at 0C for 30 minutes, before warming to ambient temperature and stirring for 24 hours. Aqueous sodium bicarbonate was then carefully added and the resultant suspension basified to pH 9 by addition of sodium carbonate. The mixture was extracted with ethyl acetate and the extracts dried over magnesium sulfate and concentrated by reduced pressure. The resultant solid was dissolved in boiling isohexane and cooled by refridgeration overnight. The resultant solid was filtered and dried to afford the title compound as colourless needles (5.4 g, 69%); NMR Spectrum: (CDCl3) 2.55 (s, 3H), 7.40 (d, 1H), 7.98 (d, 1H) ; Mass Spectrum : M+H+ 253.

The chemical industry reduces the impact on the environment during synthesis 49844-90-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2003/87057; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 4595-60-2, 2-Bromopyrimidine, 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-Bromopyrimidine, blongs to pyrimidines compound. Application In Synthesis of 2-Bromopyrimidine

Synthesis of 3-fluoro-2-(pyrimidin-2-yl)benzonitrile (Intermediate in the synthesis of intermediate A-2) To a solution of 3-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (4.98 g, 19.1 mmol) and 2-bromopyridine (3.85 g, 23 mmol) in THF (96 mL) was added Na2CO3 (6 g, 57.4 mmol) followed by water (43 mL). The reaction mixture was degassed with N2 for 10 minutes. PdCl2(dtbpf) (374 mg, 0.57 mmol) was added and the reaction mixture was stirred at 80 C. for 5 h. The solution was cooled to room temperature and a mixture of EtOAc and water was added. The aqueous was extracted twice with EtOAc and the combined organic layers were dried over MgSO4, filtered and evaporated. The title compound was precipitated by dissolving the residue in a minimum amount of EtOAc and then adding hexanes. The solid was filtered, washed with hexanes and dried to afford the title compound (2.46 g, 64%). MS (ESI) mass calcd. for C11H6FN3, 199.1; m/z found 200.1 [M+H]+. 1H NMR (400 MHz, Chloroform-d) delta 9.02-8.91 (m, 2H), 7.65 (dt, J=7.7, 1.0 Hz, 1H), 7.60-7.52 (m, 1H), 7.51-7.43 (m, 1H), 7.41 (t, J=4.9 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4595-60-2, 2-Bromopyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Janssen Pharmaceutica NV; GELIN, Christine F.; LEBOLD, Terry P.; SHIREMAN, Brock T.; US2014/275118; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia