Day: March 24, 2022

Application of 5600-21-5 , The common heterocyclic compound, 5600-21-5, name is 4-Chloro-6-methylpyrimidin-2-amine, molecular formula is C5H6ClN3, 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.

Compound 7 (1.5 g, 6.5 mmol) was dissolved in 40 ml of dichloromethane under argon, and aluminum chloride (4.4 g, 32.5 mmol) was slowly added portionwise.Then, pyridine (10.5 ml, 129.8 mmol) was gradually added to the above reaction liquid, and the mixture was heated under reflux in an oil bath at 45 C for 30 hours.The reaction was monitored by TLC until compound 7 was completely reacted.The reaction solution was cooled to room temperature, the pH of the reaction mixture was adjusted to 1 with 6M hydrochloric acid, and dichloromethane was evaporated under reduced pressure.The ether layer was washed with 1 M of dilute hydrochloric acid and saturated brine, and the ether layer was dried over anhydrous sodium sulfate.The crude product was recrystallized from ethyl acetate / n-hexane.1.3 g of solid compound 6, yield 96%.

The synthetic route of 5600-21-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan University; Wu Yong; Hai Li; Zhang Yong; Cheng Xu; Guo Lingmei; Li Weijian; Zhan Zhen; (11 pag.)CN108191878; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1060815-89-5, 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. 1060815-89-5, name is 7H-Pyrrolo[2,3-d]pyrimidine-5-carbaldehyde, molecular formula is C7H5N3O, 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 O C solution of 7H-pyrrolo[2,3-djpyrimidine-5-carbaldehyde (5.41 g, 36.8mmol) and cesium carbonate (13.18 g, 40.4 mmol) in DMF (147 ml) was added tert-butyl 2-bromoacetate (5.90 ml, 40.4 mmol). The mixture was allowed to warm up to RT byremoving from ice bath. The reaction was stirred for 2 hs. The reaction was poured ontoice water (500 mL) and EtOAc (300 mL) mixture. The product was extracted in theEtOAc. The layers were separated and the aqueous phase was extracted a second time with EtOAc (2x 150 mL). The combined EtOAc layers were washed with brine. The organic layer was collected and dried over sodium sulfate and concentrated undervacuum. The crude product was purified by silica gel chromatography to get tert-butyl 2-(5-formyl-7H-pyrrolo[2,3-djpyrimidin-7-yl)acetate 6.60 g (69%) as clean product. ESIMS(-): MS m/z 262.0.

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 1060815-89-5, 7H-Pyrrolo[2,3-d]pyrimidine-5-carbaldehyde.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MILLER, Michael Matthew; ALLEN, Martin Patrick; LI, Ling; BOWSHER, Michael S.; GILLIS, Eric P.; MULL, Eric; ZHAO, Qian; SUN, Li-Qiang; LANGLEY, David R.; SCOLA, Paul Michael; (214 pag.)WO2017/176608; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 923282-39-7, 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. 923282-39-7, name is 7-Chloro-1-methyl-1H-pyrazolo[4,3-d]pyrimidine. A new synthetic method of this compound is introduced below.

Example 4: Preparation of N-[2-[3-methoxy-4-[[2-(trifluoromethyl)-4-pyridyl]oxy]phenyl] ethyl]-1 – methyl-pyrazolo[4,3-d]pyrimidin-7-amine (1-10) To a solution of 2-[3-methoxy-4-[[2-(trifluoromethyl)-4-pyridyl]oxy]phenyl]ethanamine (0.39 g, 1 .2 mmol) in acetonitrile (30 ml.) was added triethylamine (1 .5 g, 4.8 mmol). The solution was stirred for 5 min at room temperature at which time 7-chloro-1 -methyl-pyrazolo[4,3-d]pyrimidine (0.25 g, 1 .2 mmol) was added. The reaction mixture was stirred at room temperature overnight. Water was added and was extracted with ethyl acetate (3x). The combined organic layers were washed with water, dried over Na2S04 and concentrated in vacuo. The residue was purified by HPLC to provide 85 mg (0.19 mmol, 17%) of the product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,923282-39-7, 7-Chloro-1-methyl-1H-pyrazolo[4,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BASF SE; BASF SCHWEIZ AG; GRAMMENOS, Wassilios; CRAIG, Ian Robert; BOUDET, Nadege; MueLLER, Bernd; DIETZ, Jochen; LAUTERWASSER, Erica May Wilson; LOHMANN, Jan Klaas; MONTAG, Jurith; WO2013/113715; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 29458-38-6, 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.29458-38-6, name is 6-Methoxypyrimidine-2,4(1H,3H)-dione, molecular formula is C5H6N2O3, molecular weight is 142.11, as common compound, the synthetic route is as follows.

A mixture of 2,4-dihydroxy-6-methoxypyrimidine (15g, 0.106mol) in phosphorus (III) oxychloride (400ml) was heated under reflux for 4 hours to give a solution. Excess phosphorus (III) oxychloride was removed by evaporation, the residue treated with ice/water and extracted with EtOAc. The combined extracts were washed with water, dried (Na2SO4) and the solvent removed by evaporation to give 2,4-dichloro-6-methoxypyrimidine as an oil (5.5g, 30%); NMR.3.96 (3H, s), 6.63 (IH, s); m/z_179 [MH]+.

Statistics shows that 29458-38-6 is playing an increasingly important role. we look forward to future research findings about 6-Methoxypyrimidine-2,4(1H,3H)-dione.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/31745; (2007); 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.60186-89-2, name is 4-Bromo-2,6-dimethoxypyrimidine, molecular formula is C6H7BrN2O2, molecular weight is 219.036, as common compound, the synthetic route is as follows.Recommanded Product: 60186-89-2

To a microwave vial was charged (R) -5- (1-hydroxy-2- (2, 8-diazaspiro [4.5] decan-8-yl) ethyl) -4-methylisobenzofuran-1 (3H) -one (40 mg, 0.121 mmol) , 4-bromo-2, 6-dimethoxypyrimidine (26.5 mg, 0.121 mmol) , tris (dibenzylideneacetone) dipalladium (0) (5.54 mg, 6.05 mumol) , 2-dicyclohexylphosphino-2?, 4?, 6?-triisopropylbiphenyl (11.5 mg, 0.024 mmol) , and potassium phosphate (51.4 mg, 0.242 mmol) . The vial was sealed, degased, and filled with dioxane (0.60 mL) . The reaction mixture was heated at 100 overnight, diluted with water, extracted with EtOAc. The organic layer was washed with brined, dried, evaporated to give the crude product, which was purified by silica gel column chromatography (0-10 MeOH/DCM) to afford (R) -5- (2- (2- (2, 6-dimethoxypyrimidin-4-yl) -2, 8-diazaspiro [4.5] decan-8-yl) -1-hydroxyethyl) -4-methylisobenzofuran-1 (3H) -one. LC-MS (ESI, m/z) : 469 [M+1] +.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60186-89-2, 4-Bromo-2,6-dimethoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; DONG, Shuzhi; GU, Xin; JIANG, Jinlong; SHI, Zhi-Cai; WALSH, Shawn P.; WU, Zhicai; YU, Yang; FERGUSON II, Ronald; GUO, Zhiqiang; FRIE, Jessica; SUZUKI, Takao; BLIZZARD, Timothy A.; FU, Qinghong; VANGELDER, Kelsey F.; (118 pag.)WO2016/65582; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
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. 34253-03-7, name is Methyl pyrimidine-2-carboxylate, the common compound, a new synthetic route is introduced below. Product Details of 34253-03-7

Step B: Preparation of pyrimidin-2-ylmethanol: NaBH4 (0.22 g, 5.79 mmol) was added in one portion to a solution of methylpyrimidine-2-carboxlate (0.80, 5.79 mmol) in EtOH (30 mL). The reaction mixture was left at room temperature overnight before carefully quenching with water (5.0 mL) and concentrating to dryness. The residue was taken up in MeOH and filtered. The filtrate was concentrated and was purified by flash column chromatography, eluting with CH2Cl2/MeOH (100:1) to give 0.18 g (28%) of the desired product as a yellow oil. Step B: Pyrimidin-2-ylmethanol: A solution of methyl pyrimidine-2-carboxylate (659 mg, 4.77 mmol, 1.00 equiv) in 25 mL EtOH was cooled to 0 C. in an ice bath, and sodium borohydride (181 mg, 4.77 mmol, 1.00 equiv) was added. The reaction mixture was warmed to ambient temperature, and stirred 2 hours, and then 5 ml water was added. The reaction was concentrated under reduced pressure, and the residue was purified using silica gel chromatography to give the desired product as a white solid (154 mg, 30%).

The synthetic route of 34253-03-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Miknis, Greg; Lyssikatos, Joseph P.; Laird, Ellen; Tarlton, Eugene; Buckmelter, Alexandre J.; Ren, Li; Rast, Bryson; Schlacter, Stephen T.; Wenglowsky, Steven Mark; US2007/49603; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 60025-06-1, 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 60025-06-1 as follows.

A solution of 1-(4,6-dichloropyrimidin-5-yl)ethanone (3.81 g, 19.9 mmol) in 90 mL of dioxane at 0 0C was treated with triethylamine (2.78 mL, 19.9 mmol) and hydrazine hydrate (1.16 mL, 23.9 mmol). After addition, the reaction was stirred for 18 h at rt. The mixture was filtered and the precipitate washed with dioxane. The combined organics were evaporated and chromatographed on silica gel, eluting with 30-35% ethyl acetate/ hexanes to afford 2.98 g, (89%) of 4-chloro-3-methyl-1 H-pyrazolo[3,4-d]pyrimidine; 1H NMR (500 MHz, DMSO-cfe) delta 8.71 (1H), 2.60 (3H) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,60025-06-1, its application will become more common.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2006/90261; (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. 31737-09-4, name is 6-Chloro-1-methylpyrimidine-2,4(1H,3H)-dione. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C5H5ClN2O2

Intermediate 1 (300 mg, 1 eq.), phenylboronic acid (296 mg, 1.3 eq.), tetrakis(triphenylphosphine)palladium (108 mg, 0.05 eq.) and 2N aqueous sodium carbonate solution (654ul, 3 eq.) were mixed in 5 ml of glycol dimethyl ether and reacted under microwave at 120 C for 50 min. The mixture was cooled and evaporated to remove solvent. Water was added and the mixture was extracted with dichloromethane twice, rinsed with saturated brine once, dried over sodium sulfate, filtered, and evaporated to remove solvent to give 310 mg of intermediate 23a. MS (ESI): 203(M+H)

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, 31737-09-4, 6-Chloro-1-methylpyrimidine-2,4(1H,3H)-dione.

Reference:
Patent; Shanghai Institute Of Materia Medica Chinese Academy of Sciences; SHEN, Jianhua; WANG, Yiping; CHEN, Xinde; XU, Wenwei; WANG, Kai; (84 pag.)EP3239135; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 774549-55-2, 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 774549-55-2 as follows.

EXAMPLES 32-34 Other N-((dimethylamino)methylene)pyrazolo (1,5-a)-pyrimidine-3-carboxamide and N-((dimethylamino) methylene)-4,5-dihydropyrazolo(1,5-a)pyrimidine-3-carboxamide products which are prepared from corresponding pyrazolo(1,5-a)pyrimidine-3-carboxamide or the 4,5-dihydropyrazolo(1,5-a)pyrimidine-3-carboxamide intermediate compounds by heating with N,N-dimethylformamide dimethyl acetal in the manner described in Examples 20-22 are listed in Table IX.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,774549-55-2, its application will become more common.

Reference:
Patent; American Cyanamid Company; US5059691; (1991); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 74647-39-5, 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 74647-39-5 as follows.

4-phenylpyrimidine-2-carboxylic acid (0.01 mol)Dissolved in 15 mL of thionyl chloride,Reflux reaction 5-7h, evaporated to dryness,The obtained solid was vacuum-dried and stored,To give the intermediate 4-phenylpyrimidine-2-carbonyl chloride.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,74647-39-5, its application will become more common.

Reference:
Patent; Shenyang Pharmaceutical University; Gong, Ping; Zhao, Yanfang; Liu, Yaijing; Di, Xin; Tang, Qidong; (42 pag.)CN104072480; (2016); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia