Day: March 23, 2022

Reference of 29509-92-0 ,Some common heterocyclic compound, 29509-92-0, molecular formula is C11H9ClN2, 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 mixture of 4-chloro-6-methyl-2-phenylpyrimidine (1 g, 4.89 mmol) and piperidine-4-carboxamide (0.627 g, 4.89 mmol) and trimethylamine (1.02 mL, 7.34 mmol) in anhydrous DMF (25 mL) was heated to reflux for 4 hours, upon completion, the reaction mixture was cooled to room temperature, and then was concentrated to dry, the residue was stirred in a mixed solution of EtOAc (10 mL) and water (20 mL) for about 30 min. and then the solid product was collected by filtration to obtain 1.4 g compound, then it was re-crystallized from EtOH/H20, after dry obtained 900 mg of the title compound as a white solid in 62% yield. MS (MH+) 297.

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. 29509-92-0, 4-Chloro-6-methyl-2-phenylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FIRMENICH INCORPORATED; SERVANT, Guy; CHEN, Qing; FOTSING, Joseph, R.; ZHANG, Lan; PATRON, Andres; WILLIAMS, Mark; BRADY, Thomas; PRIEST, Chad; DARMOHUSODO, Vincent; SIMONE, Kenneth; WONG, Melissa, S.; (204 pag.)WO2020/33669; (2020); 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.25746-87-6, name is 4-Dimethoxymethylpyrimidine, molecular formula is C7H10N2O2, molecular weight is 154.17, as common compound, the synthetic route is as follows.HPLC of Formula: C7H10N2O2

To the solution of 3.90 g of 4-(dimethoxymethyl)pyrimidine (25.3 mmol) in 100 mLAcOll 4.15 g sodium acetate (50.6 mmol) and 8.08 g bromine (50.6 mmol) were addedand the mixture was stirred at 40C for 7 h. Reaction mixture was concentrated underreduced pressure, DCM was added to the residue, and it was washed with saturated aq.NaHCO3. The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified via flash chromatography using heptane and EtOAc as eluents to give 5-bromo-4-(dimethoxymethyl)pyrimidine, 1HNMR(400 MHz, DMSO-d6): 9.18 (s, 111), 9.06 (s, 111), 5.51 (s, IH), 3.40 (s, 611).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,25746-87-6, 4-Dimethoxymethylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; LES LABORATOIRES SERVIER; VERNALIS (R&D) LIMITED; KOTSCHY, Andras; SZLAVIK, Zoltan; CSEKEI, Marton; PACZAL, Attila; SZABO, Zoltan; SIPOS, Szabolcs; RADICS, Gabor; PROSZENYAK, Agnes; BALINT, Balazs; BRUNO, Alain; GENESTE, Olivier; DAVIDSON, James Edward Paul; MURRAY, James Brooke; CHEN, I-Jen; PERRON-SIERRA, Francoise; WO2015/97123; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1398507-08-8, 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.1398507-08-8, name is 4-((4-Amino-6-chloropyrimidin-2-yl)amino)benzonitrile, molecular formula is C11H8ClN5, molecular weight is 245.67, as common compound, the synthetic route is as follows.

Example 4: Preparation of N-[6-Chloro-2-(4-cyanophenylamino)pyrimidin-4- yl]benzamide (IV)1400 ml of N-methyl pyrrolidine and 140 g of 4-(4-Amino-6-chloropyrimidin-2- ylamino)benzonitrile was charged into a reaction vessel. To this was added 85.49 g of dimethylamino pyridine and 87.2 lg of diazabicyclo undecene and stirred for 30 mins. To the reaction mixture was added 27.36 g of benzoyl chloride and stirred at RT for 30mins and heated to 80- 85 C and maintained the same for 4 hrs. After completion of the reaction, the reaction mass was cooled to RT and was added 1400 ml of water followed by 1400 ml of 50% carbonate solution. Reaction mass was extracted with 1400 ml of dichloromethane and the dichloromethane layer was washed with 700 ml of water. The organic layers were separated and dried over of anhydrous sodium sulfate and filtered; distilled off dichloromethane and the solid was isolated.

Statistics shows that 1398507-08-8 is playing an increasingly important role. we look forward to future research findings about 4-((4-Amino-6-chloropyrimidin-2-yl)amino)benzonitrile.

Reference:
Patent; MYLAN LABORATORIES LTD; GORE, Vinayak; BHARATI, Choudhari; HUBLIKAR, Mahesh; BANSODE, Prakash; SINORE, Sandip; WO2012/147104; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1211522-68-7, 4,6-Dichloro-3-methyl-1H-pyrazolo[3,4-d]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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

4,6-Dichloro-3-methyl-1H-pyrazolo [3,4-d] pyrimidine(70 mg, 0.34 mmol) was added to ethyl acetate (2 mL), and dihydropyran (0.2 mL, 2.3 mmol) and p-toluenesulfonic acid (3 mg) were added. The mixture was stirred at 50 C for 12 hours. Upon completion of the reaction, the reaction mixture was extracted with ethyl acetate and water, and the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. The concentrate was subjected to column chromatography to obtain the target compound. (30 mg, 54%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1211522-68-7, 4,6-Dichloro-3-methyl-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Korea Research Institute of Chemical Technology; Cho Seong-yun; Kim Pil-ho; Lee Jeong-ok; Kim Hyeong-rae; Ha Jae-du; Jeong Hui-jeong; Yoon Chang-su; Park Ji-hun; Hwang Jong-yeon; (76 pag.)KR2018/137057; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 17758-52-0 ,Some common heterocyclic compound, 17758-52-0, molecular formula is C5H6N2O, 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 mixture of 5-methyl-3/-/-pyrimidin-4-one (0.60 g, 3.6 mmol) and phosphorous oxychloride (2.0 ml.) was heated at 90 0C for 2.5 h. The mixture was evaporated to dryness under reduced pressure and the resultant solid was purified by sublimation under reduced pressure to furnish the title compound as a white solid. This compound was unstable to air and was used immediately in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17758-52-0, its application will become more common.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; McDONALD, Edward; BLAGG, Julian; PICHOWICZ, Mark; CRUMPLER, Simon Ross; WO2010/41054; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 54368-61-5, name is Ethyl 2,6-dichloro-5-nitropyrimidine-4-carboxylate, molecular formula is C7H5Cl2N3O4, 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. Safety of Ethyl 2,6-dichloro-5-nitropyrimidine-4-carboxylate

4) 15 g of ethyl 2,4-dichloro-5-nitro-6-pyrimidinecarboxylic acid, 10 g of palladium on carbon, 5 g of magnesium oxide,Add 150 ml of THF, hydrogenate for 7 hours, filter, and apply with palladium and carbon recovery.The filtrate was evaporated to dryness to obtain a crude product. Column chromatography5.5 g of ethyl 2-chloro-5-amino-6-pyrimidinecarboxylic acid was obtained, more than 98%,The yield was 48%.

With the rapid development of chemical substances, we look forward to future research findings about 54368-61-5.

Reference:
Patent; Nanjing Puruida Pharmaceutical Technology Co., Ltd.; Wang Xiaobo; (6 pag.)CN110452180; (2019); A;,
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.69696-37-3, name is 5-Bromo-2,4-dimethylpyrimidine, molecular formula is C6H7BrN2, molecular weight is 187.0372, as common compound, the synthetic route is as follows.Recommanded Product: 5-Bromo-2,4-dimethylpyrimidine

Intermediate B1 (0351) A mixture of B1.4 (12 g, 64 mmol), bis(pinacolato)diboron (22.8 g, 89.6 mmol, 1.4 eq), KOAc (18.8 g, 192 mmol, 3.0 eq), and Pd(dppf)Cl2 (2.34 g, 3.2 mmol) in 200 mL of anhydrous dioxane was heated at 90 C. and stirred for 4 h under N2. The solvent was removed under reduced pressure, the residue was diluted with 300 mL mixed slovent (PE:EA=4:1), filtered and concentrated. The crude product was purified by flash column chromatography (PE:EA=2:1 to 1:1) to give the title compound (10 g, 66%) as a yellow oil. LC-MS: [M+H]+=235.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,69696-37-3, 5-Bromo-2,4-dimethylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Novartis AG; CHAN, Ho Man; GU, Xiang-Ju Justin; HUANG, Ying; LI, Ling; MI, Yuan; QI, Wei; SENDZIK, Martin; SUN, Yongfeng; WANG, Long; YU, Zhengtian; ZHANG, Hailong; ZHANG, Ji Yue (Jeff); ZHANG, Man; ZHANG, Qiong; ZHAO, Kehao; (134 pag.)US2016/176882; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 19808-30-1, 5-Bromopyrimidin-4(3H)-one, 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, 19808-30-1, blongs to pyrimidines compound. Application In Synthesis of 5-Bromopyrimidin-4(3H)-one

EXAMPLE 12: 5-bromo-4-chloropyrimidine15 A stirred solution of 5-bromopyrimidin-4-ol (650mg, 3.73mmol) in POCI3 (in excess) was heated at 100C overnight. The reaction mixture was cooled and concentrated under reduced pressure. Crude product was dissolved in ethyl acetate and this mixture was slowly poured into saturated sodium bicarbonate solution. The ethyl acetate layer was separated and washed with brine solution, and dried over anhydrous sodium sulphate and concentrated to get the desired product 15 as yellow solid, 300mg (Yield- 43%). The product was confirmed by 1HNMR and MS spectrum analysis. 1H NMR (400 MHz, CDC13) delta: 8.86 (s, 1H), 8.82 (s, 1H); MS- 192 (M+l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,19808-30-1, its application will become more common.

Reference:
Patent; ARRIEN PHARMAEUTICALS LLC; VANKAYALAPATI, Hariprasad; APPALANENI, Rajendra, P.; REDDY, Y., Venkata Krishna; WO2012/135631; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 53557-69-0, 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 53557-69-0, name is 6-Iodopyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

Description 94; 6-(1 8-Naphthyridin-2-yl) pvrimidin-4-amine; To a mixture of Description 92 (2.52 g, 15. 3 mmol), hexamethylditin (5.0 g, 15.3 mmol), lithium chloride (1.95 g, 45.9 mmol), and copper (I) iodide (291 mg, 1.53 mmol) in anhydrous 1,4-dioxane (50 ml) was added Pd (PPh3) 4 (884 g, 0.77 mmol). The mixture was de-gassed three times, and heated at 100C overnight. The mixture was cooled and diluted with EtOAc (120 ml) and washed with a 10% potassium fluoride solution (200 ml). The organic layer was washed with sat. NaCl (50 ml), dried over Na2SO4, filtered, and evaporated. The residue was taken up in anhydrous 1,4-dioxane (75 ml), and Description 93 (1.55 g, 7 mmol), lithium chloride (1.78 g, 42 mmol), and copper (I) iodide (266 mg, 1.4 mmol) added, followed by Pd (PPh3) 4 (808 mg, 0.7 mmol). The mixture was de-gassed 3 times and heated at 100C for 3 days. The mixture was poured into water (200 ml), and extracted with EtOAc (2 x 100 ml), the combined EtOAc layers were washed with water (150 ml), sat. NaCl (100 ml), dried over Na2SO4, filtered and evaporated. The residue was purified by column chromatography on silica (eluent: 2% MeOH in DCM + 0.5% NH40H) to give the title compound (100 mg, 3%).’H NMR (360 MHz, DMSO-d6) 7.18 (2 H, br s), 7.66-7. 86 (3 H, m), 8.55 (1 H, dd, J 8.1 and 1. 8), 8. 58 (1 H, d, J4. 2), 8.64 (1 H, d, J8. 4), 9.16 (1 H, dd, J4. 2 and 2.1).

According to the analysis of related databases, 53557-69-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2005/47279; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 259809-79-5 , The common heterocyclic compound, 259809-79-5, name is tert-Butyl 7,8-dihydro-2-(methylsulfonyl)pyrido[4,3-d]pyrimidine-6(5H)-carboxylate, molecular formula is C13H19N3O4S, 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.

Under nitrogen atmosphere, 2,2-difluoroethanol (65.5 mg, 0.80 mmol) dissolved in DMF (2 mL) was cooled with ice. To the solution was added sodium hydride (60 wt percent, 31.9 mg, 0.80 mmol) portionwise. The mixture was stirred at 0° C. for 1 hour. To the mixture was added a compound 27 (50 mg, 0.16 mmol) portionwise. Then, the mixture was stirred at 0° C. for 2 hours. Ice water was added to the reaction mixture. The mixture was extracted with ethyl acetate. The organic layer was washed by brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica-gel column chromatography (hexane-ethyl acetate) to give a compound 28 (28.8 mg, yield 57percent).1H-NMR (CDCl3) delta: 1.50 (s, 9H), 2.89 (s, 2H), 3.73 (s, 2H), 4.53-4.61 (m, 4H), 6.14 (t, J=55.4 Hz, 1H), 8.27 (s, 1H).

The synthetic route of 259809-79-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi & Co., Ltd.; TOBINAGA, Hiroyuki; MASUDA, Koji; KASUYA, Satoshi; INAGAKI, Masanao; YONEHARA, Mitsuhiro; MASUDA, Manami; (289 pag.)US2019/161501; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia