Month: September 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.5305-59-9, name is 6-Chloropyrimidin-4-amine, molecular formula is C4H4ClN3, molecular weight is 129.55, as common compound, the synthetic route is as follows.Product Details of 5305-59-9

Reference Example 9 6-Aminopyrimidine-4-carboxylic acid propyl ester A mixture of 6-chloro-4-aminopyrimidine (2.00 g, 15.4 mmol), palladium acetate (361 mg, 1.61 mmol), 1,3-bis(diphenylphosphino)propane (631 mg, 1.52 mmol), and potassium carbonate (2.55 g, 18.5 mmol) in n-propanol (45 mL) and DMF (15 mL) was stirred at 90C under carbon monoxide atmosphere. The mixture was allowed to stand and cool to room temperature, and then filtered through Celite. Aqueous sodium bicarbonate solution was added to the filtrate, which was extracted with ethyl acetate. The organic phase was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated off in vacuo. The residue was purified by column chromatography on silica gel (chloroform/methanol = 100/1 to 50/1) to give the title compound (1.86 g, 10.3 mmol, yield 67%). 1H-NMR (delta ppm, CDCl3): 8.71 (d, J = 1.2 Hz, 1H), 7.17 (d, J = 1.2 Hz, 1H), 5.16 (br, 2H), 4.35 (t, J = 6.9 Hz, 2H), 1.83 (tq, J = 7.4, 6.9 Hz, 2H), 1.02 (t, J = 7.4 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5305-59-9, 6-Chloropyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2070927; (2009); 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. 146533-41-7, name is 5-(4-Bromophenyl)-4,6-dichloropyrimidine, molecular formula is C10H5BrCl2N2, 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. Product Details of 146533-41-7

To a solution of 5-(4-bromophenyl)-4,6-dichloro-pyrimidine (100 g) in dimethyl sulfoxide (700 ml), potassium(N-propylsulfamoyl)amide (145 g) was added at 25-30C under nitrogen atmosphere and stirred for 10 hrs. After reaction completion, pH of the reaction mass was adjusted to 2-3 using aqueous hydrochloric acid at 25-30C and stirred for 75 mins. The solid obtained was filtered, washed with water and suck dried under vacuum. Methanol (3500 ml) was added to the above compound and heated to reflux temperature then stirred for an hour at reflux. The reaction mass was distilled upto 450-550 mL remained in the flask. The reaction mass was cooled to 25-30C, stirred for 75 mins then further cooled to 0- 5C and stirred for 75 mins. The obtained solid was filtered, washed with methanol and dried under vacuum at 50-55C for 4 hrs to get the title compound. Yield: 110 g; Purity by HPLC: 99.10%

With the rapid development of chemical substances, we look forward to future research findings about 146533-41-7.

Reference:
Patent; LAURUS LABS PRIVATE LIMITED; JAMJANAM, Srivardhana Rao; MOTURU, Venkata Ramakrishna Murthy; INDUKURI, Venkata Sunil Kumar; KALIDINDI, Srihari Raju; CHAVA, Satyanarayana; (37 pag.)WO2017/93903; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 24415-66-5, 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 24415-66-5 as follows.

Adding 85 mg (about 0.5 mmol) to a 10 mL microwave reaction tube.7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine and 228 mg (about 1.5 mmol) of 6-chloroindole, 14 mg (about 10 mol%) of the catalyst bistrifluoromethylsulfonimide and 1 mL of the solvent HFIP, and then the microwave reaction tube was sealed.Then, the reactant in the microwave reaction tube was stirred at 100 C for 6 hours, and the solvent was distilled off under reduced pressure.And purified by column chromatography using DCM / MeOH as eluent to give about 108 mg of pure product e9 as a yellow solid with a yield of 76%;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,24415-66-5, its application will become more common.

Reference:
Patent; Zhengzhou University; Liu Hongmin; Yu Bin; Yuan Shuo; Wang Shuai; Li Zhonghua; (21 pag.)CN109180684; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 23906-13-0, Adding some certain compound to certain chemical reactions, such as: 23906-13-0, name is 2-Hydrazinyl-4,6-dimethylpyrimidine,molecular formula is C6H10N4, 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 23906-13-0.

General procedure: An ethanolic solution (25 mL) of 2-hydrazino-4,6-dimethylpyrimidine 1 (0.27 g, 2 mmol) and trifluoromethyl-bdiketones 2a-c (2 mmol) was refluxed for 7 h. The reaction was monitored by tlc. On completion of reaction, solvent was evaporated in vacuo and the solid obtained was recrystallized from ethanol. The tlc and 1H NMR of the reaction mixture showed the formation of a single product 3a-c.

According to the analysis of related databases, 23906-13-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Aggarwal, Ranjana; Bansal, Anshul; Rozas, Isabel; Kelly, Brendan; Kaushik, Pawan; Kaushik, Dhirender; European Journal of Medicinal Chemistry; vol. 70; (2013); p. 350 – 357;,
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. 147118-37-4, name is N-(4-(4-Fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide, the common compound, a new synthetic route is introduced below. Application In Synthesis of N-(4-(4-Fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide

Example 6b Using NaHMDS N-(4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide (0.5 g, 1.4 mmol) and 2-((4 ,6S)-6-((benzo[d]thiazol-2-ylsulfonyl)methyl)-2,2-dimethyl- 1 ,3-dioxan-4-yl)acetate te/f-butyl ester (0.7 g, 1.6 mmol) were added to 10 mL of dry THF. After stirring for 10 min at 20C, the reaction mixture was cooled to -70C. At this temperature 1.9 mL of NaHMDS solution (1 M in THF, total 3.8 mmol) was added in 60 min keeping the temperature between -70 and -75C. When dosing was completed, the temperature of the reaction mixture was allowed to increase to -10C. After stirring at this temperature for 1 h, the reaction was quenched with 10% aqueous NaHC03 (5 mL). The phases were separated. The aqueous layer was extracted with 2 x 20 mL of ethyl acetate. The combined organic phases were washed with 5% aqueous Na2C03 and concentrated under vacuum. H PLC analysis indicated an E to Z ratio of >99: 1 . The residue was crystallized from methanol to give 2-((4f?,6S)-6-((E)-2-(4-(4-fluorophenyl)-6- isopropyl-2-(N-methylmethylsulfonamido) pyrimidin-5-yl)vinyl)-2,2-dimethyl-1 ,3-dioxan- 4-yl)acetate, te/f-butyl ester as a solid (0.52 g, 0.9 mmol, 64% yield).

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

Reference:
Patent; DSM SINOCHEM PHARMACEUTICALS NETHERLANDS B.V.; DE LANGE, Ben; RIEBEL, Peter, Hans; WOLBERG, Michael; HEEMSKERK, Dennis; MINK, Daniel; WO2012/98048; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 180869-36-7, Adding some certain compound to certain chemical reactions, such as: 180869-36-7, name is 4-(Dimethoxymethyl)-2-(methylthio)pyrimidine,molecular formula is C8H12N2O2S, 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 180869-36-7.

(11-[2″{4″Pgperldinyloxy)-4-pyrjmi’dg?yf]ethyl}oxy)-2-th|opheStep A – 4-[Bis(methy.oxy)methy l]-2-(methylsuifonyl)pyrimidine4-[betais(methyfoxy)methyl]-2-(methyithlo)pyrimldme (US Patent 6218537, 2001) (8.24 g, 46.1 mmo.) was dissolved s? 150 mL of DCM and cooled to 0 C with stirring. 3-Chloroperoxybenzoic acid (23.87 g, 70%, 98.8 rnmoi) was added in a single portion. The reaction was altowed to reach r? slowly, The reaction was stirred 2 h and quenched by the addition of 150 ml of 10% sodium sulfite solution. The mixture was poured into a separatory funnel and the layers were separated. The organic layer was washed with 150 mL of 10% Na2COs solution (2X) and brine (IX). The organic layer was dried over ^IgSO4, filtered, and concentrated in vacuo. Purification by Hash chromatography afforded 10.25 g (98%) of the title compound. 1H NMR (400 IVlHz8 CDCb) S 8.96 (d, J- 4.9 Hz1 1 H), 778 (d , J^- 4.9 Hz, 1 H), 5.34 (s, 1 H), 3.48 (s, 6H), 3.38 (s, 3H).

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. 180869-36-7, 4-(Dimethoxymethyl)-2-(methylthio)pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/143456; (2007); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 19810-79-8, 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. 19810-79-8, name is 2-Morpholinopyrimidin-4-ol, molecular formula is C8H11N3O2, 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.

2c) 4- (4-BROMO-PVRIMIDIN-2-VL)-MORPHOLINE A mixture of 2-morpholin-4-yl-pyrimidin-4-ol (6.08 g, 33.6 MMOL) and phosphorus OXYBROMIDE (12.5 g, 43.7 MMOL) in 330 mL MECN is heated to reflux for 1 hour. The reaction is cooled to room temperature, concentrated to half volume, and poured over ice. The resulting mixture is neutralized with a saturated solution of NaHCOs, and then extracted with methylene chloride. The organic phase is washed with saturated NACI (aqueous), dried over ANHYDROUS MGS04, FILTERED, concentrated and dried to an off-white solid (7.11 g, 87%). M+H’= 245.97. H NMR (CDC13) ; a 8.05 (d, 1H), 6.70 (d, 1H), 3.75 (m, 8H).

According to the analysis of related databases, 19810-79-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/28444; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 56686-16-9, 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 56686-16-9, name is 5-Bromo-2,4-dimethoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a stirred anhydrous THF containing 5-bromo-2,4-dimethoxypyrimidine (0.29g, 1.3mmol) was added dropwise a 2.5M n-BuLi/hexane solution (0.6mL, 1.4mmol) at 195K under argon atmosphere. After 30min, 8a (0.52g, 1.3mmol) was added and the reaction mixture was stirred for 2h at this temperature. The reaction was allowed to warm to room temperature and quenched by addition of water. The product was extracted with diethyl ether. Then the combined organic layers were dried over MgSO4, filtered and concentrated. Column chromatography on SiO2 with petroleum ether and ethyl acetate (v/v=6/1) as the eluent afforded 0.35g of 1o as a colorless solid in 52% yield.

According to the analysis of related databases, 56686-16-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Hongliang; Pu, Shouzhi; Liu, Gang; Chen, Bing; Dyes and Pigments; vol. 102; (2014); p. 159 – 168;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 514854-12-7, 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 514854-12-7 as follows.

A suspension of 2,4-diamino-6-ethylpyrimidine (0.8750 g, 5.00 mmol) and iodine monochloride (0.40 mL, 7.50 mmol) in methanol (15 mL) was stirred at roomtemperature for 2 hours. Water (5 mL) was added and adjusted pH to 7 with 10% aq NaOH. The reaction was extracted 3 times with ethyl acetate (15 mL each), dried over anhydrous MgSO4 and evaporated. The product was obtained as a light brown solid (1.1355 g, 86% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,514854-12-7, its application will become more common.

Reference:
Patent; NATIONAL SCIENCE AND TECHNOLOGY DEVELOPMENT AGENCY; KAMCHONWONGPAISON, Sumalee; CHAROENSETAKUL, Netnapa; PEEWASAN, Krisana; VANICHTANANKUL, Jarunee; RATTANAJAK, Roonglawan; TAWEECHAI, Supannee; ANUKUNWITHAYA, Tosapol; YOOMUANG, Aphisit; YUTHAVONG, Yongyuth; VILAIVAN, Tirayut; (44 pag.)WO2017/52479; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 13479-88-4, 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. 13479-88-4, name is 5,7-Dichlorothiazolo[5,4-d]pyrimidine, molecular formula is C5HCl2N3S, 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.

Step 5N-(3-(2-Oxa-6-azaspiro[3.3]heptan-6-yl)phenyl)-5-chlorothiazolo[5,4-d]pyrimidin-7-amine Procedure:A mixture of 5,7-dichlorothiazolo[5,4-d]pyrimidine (108 mg, 0.526 mmol), 3-(2-oxa-6-azaspiro[3.3]heptan-6-yl)aniline (100 mg, 0.526 mmol) and DIEA (102 mg, 0.789 mmol) in 5 mL of DMSO was stirred at room temperature for 16 hours. The mixture was poured into water and the precipitate was filtered. The crude N-(3-(2-oxa-6-azaspiro[3.3]heptan-6-yl)phenyl)-5-chlorothiazolo[5,4-d]pyrimidin-7-amine (160 mg, 85%) was used into the next step without purification. LC-MS: 360 [M+H]+, tR=1.53 min.

According to the analysis of related databases, 13479-88-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hermann, Johannes Cornelius; Lowrie, JR., Lee Edwin; Lucas, Matthew C.; Luk, Kin-Chun Thomas; Padilla, Fernando; Wanner, Jutta; Xie, Wenwei; Zhang, Xiaohu; US2012/252777; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia