Tag: M.W:100-200

Synthetic Route of 17180-94-8, Adding some certain compound to certain chemical reactions, such as: 17180-94-8, name is 5-Chloropyrimidine,molecular formula is C4H3ClN2, 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 17180-94-8.

A 100 mL round-bottom flask was charged with 5-chloropyrimidine (5 mmol), phenylboronic acid (1.22 g, 10 mmol), PPh3 (265 mg, 1 mmol) and Pd(OAc)2 (224 mg, 1 mmol) in dioxide (50 mL) under nitrogen at room temperature. After stirring for 30 minutes, Na2C03 (159 mg, 7.5 mmol) and H20 (10 mL) were added and the resulting mixture was heated at reflux for 3 h. After cooling to rt, the reaction mixture was poured into water and extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with brine (3 x 50 mL) and dried over anhydrous Na2S04. After filtration and concentration, the crude product was purified by column chromatography to give the title compound.

According to the analysis of related databases, 17180-94-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUNOVION PHARMACEUTICALS INC.; CAMPBELL, John, Emmerson; CAMPBELL, Una; HANANIA, Taleen, G.; SHAO, Liming; WO2013/119895; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 14631-08-4 , The common heterocyclic compound, 14631-08-4, name is 2-Chloropyrimidine-4,5-diamine, molecular formula is C4H5ClN4, 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 21-3 (4 g, 27.6 mmol) and compound 21-3-1 (5.2 g, 31.2 mmol) were dissolved in HCl/i-PrOH (2 mL/40 mL), and the mixture was heated to 100 C. and stirred for 14 h, followed by adjusted to pH 9 with Na2CO3 (aq.) and extracted with DCM (50 mL×4). The organic phase was dried over anhydrous Na2SO4, filtered and concentrated to give a crude product which was purified by column chromatography to afford compound 21-4 (1.1 g, Yield 14.7%) as black solid.

The synthetic route of 14631-08-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hubei Bio-Pharmaceutical Industrial Technological Institute Inc.; Humanwell Healthcare (Group) Co., Ltd.; Wang, Xuehai; Wu, Chengde; Xu, Yong; Shen, Chunli; Li, Li’e; Hu, Guoping; Yue, Yang; Li, Jian; Guo, Diliang; Shi, Nengyang; Huang, Lu; Chen, Shuhui; Tu, Ronghua; Yang, Zhongwen; Zhang, Xuwen; Xiao, Qiang; Tian, Hua; Yu, Yanping; Chen, Hailiang; Sun, Wenjie; He, Zhenyu; Shen, Jie; Yang, Jing; Tang, Jing; Zhou, Wen; Yu, Jing; Zhang, Yi; Liu, Quan; (251 pag.)US2017/313683; (2017); 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. 108-53-2, name is 2-Aminopyrimidin-4(1H)-one, molecular formula is C4H5N3O, 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. HPLC of Formula: C4H5N3O

Step 1-Synthesis of 2-amino-5-nitro-3,4-dihydropyrimidin-4-one Concentrated sulfuric acid (2.4 mL) was added to 2-amino-3,4-dihydropyrimidin-4-one (1 g, 9.0 mmol). The mixture was stirred and cooled in ice bath before dropwise addition of concentrated nitric acid (0.56 mL). The mixture was stirred at RT for 30 min before being heated at 70 C. for 2 hr. The mixture was allowed to cool to RT and was slowly added to water (10 mL), cooled in an ice bath. The resultant precipitate was collected by suction filtration, washed with diethyl ether (5 mL) and then thoroughly dried under high vacuum to give the title compound: 1H NMR (250 MHz, DMSO) delta 7.18 (1H, br. s.), 8.61 (1H, br. s.), 8.81 (1H, s); LC-MS: m/z=+156.9 (M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 108-53-2.

Reference:
Patent; Genentech, Inc.; US2012/214762; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 6960-17-4, 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. 6960-17-4, name is 2,5-Dimethoxypyrimidin-4-amine, molecular formula is C6H9N3O2, 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.

Example 6Preparation of Ethyl [(2,5-dimethoxypyrimidin-4-yl)amino]carbono-thioylcarbamate 2,5-Dimethoxypyrimidin-4-amine (6) (3 g, 0.0193 moles) was dissolved in 18 g of ethyl acetate. Ethyl isothiocyanatidocarbonate (2.77 g, 0.0208 moles) was added in one portion. The solution was heated to 78 C. and held at that temperature for 11 h. An additional 1.4 g of the ethyl isothiocyanatidocarbonate was added and the mixture heated for 2.5 h. The mixture was allowed to cool to 22 C. and filtered. The resulting solid was washed with ethyl acetate (20 mL) and dried to a constant weight in a fume hood to afford the title compound as a yellow solid (4.81 g, 89%): 13C NMR (DMSO-d6, 100 MHz) delta 177.5, 158.4, 153.3, 149.5, 142.3, 139.5, 62.6, 57.6, 55.2, 14.4; HRMS (ESI), calcd for C10H14N4O4S, 286.0736; found, 286.0727.

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 6960-17-4, 2,5-Dimethoxypyrimidin-4-amine.

Reference:
Patent; DOW AGROSCIENCES LLC; US2011/295003; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 20924-05-4, 2-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetic acid, 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, 20924-05-4, blongs to pyrimidines compound. COA of Formula: C7H8N2O4

EXAMPLE 64. 1-(4-METHYL-THIAZOLE-2-SULFONYL)-4-[(THYMIN-1-YL)-ACETYL]-PIPERAZIN-2- one [00377] To 3 mL of DMF, were added 0.30 g (0.8 mmol) OF 4- (4-METHYL-THIAZOLE-2-SULFONYL)- piperazin-2-one trifluoroacetic acid salt, 0.147 g (0.8 mmol) of (thymin-1-yl)-acetic acid and 0.458 g of PYBOP. The reaction mixture was stirred for 4hours at room temperature. Almost of the solvent was removed in vacuo and the residue was dissolved in methylene chloride. The solution was washed with saturated sodium bicarbonate solution, water, 1N HCI, water and brine sequencially. The organic layer was concentrated and column chromatographed on silicagel to give 0.19 g (56%) OF THE title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,20924-05-4, its application will become more common.

Reference:
Patent; PANAGENE INC.; WO2005/9998; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 43088-67-1, 4-Chloro-5-methylthieno[2,3-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, Formula: C7H5ClN2S, blongs to pyrimidines compound. Formula: C7H5ClN2S

4-Chloro-5-methyl-thieno[2,3-d]pyrimidine (32 mg), 2-phenyl-[1,8]naphthyridin-3-ol (39 mg), and 4-dimethylaminopyridine (64 mg) were suspended in 1,2-dichlorobenzene (1 ml), and the suspension was stirred at 130C for 2.5 hr. The reaction mixture was cooled to room temperature, and an aqueous sodium hydrogencarbonate solution was added to the reaction mixture. The organic layer was extracted with chloroform, and the chloroform layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography with a methanol-chloroform system to give the title compound (62 mg, yield 99%). 1H-NMR (CDCl3, 400 MHz): delta 2.61 (d, J = 1.2 Hz, 3H), 7.09 (d, J = 1.5 Hz, 1H), 7.31 – 7.35 (m, 3H), 7.54 (dd, J = 4.1, 8.1 Hz, 1H), 7.92 (m, 2H), 8.15 (s, 1H), 8.25 (dd, J = 1.7, 8.1 Hz, 1H), 8.42 (s, 1H), 9.17 (dd, J = 2.0, 4.1 Hz, 1H) Mass spectrometric value (ESI-MS, m/z): 371 (M+1)+

The synthetic route of 43088-67-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1724268; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 66522-06-3, Adding some certain compound to certain chemical reactions, such as: 66522-06-3, name is 4-(tert-Butyl)-2-chloropyrimidine,molecular formula is C8H11ClN2, 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 66522-06-3.

A mixture of 4-tert-butyl-2-chloropyrimidine (1.1 g, 6.4 mmol), 33% methylamine in ethanol (1 mL) in ethanol (4 mL) was placed in a sealed tube and heated to 60 C. for 3 h. The mixture was concentrated and the solid dissolved in chloroform. The organic layer was washed with water, dried over sodium sulfate, concentrated and chromatographed on silica gel with 30% EtOAc/Hexane. MS m/z 165 (MH)+.

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. 66522-06-3, 4-(tert-Butyl)-2-chloropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Andersen, Denise Lyn; Chang, Catherine H.; Falsey, James R.; Frohn, Michael J.; Hong, Fang-Tsao; Liao, Hongyu; Liu, Longbin; Lopez, Patricia; Retz, Daniel Martin; Rishton, Gilbert M.; Rzasa, Robert M.; Siegmund, Aaron; Tadesse, Seifu; Tamayo, Nuria; Tegley, Christopher M.; US2006/69110; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1250967-81-7, 2-Chloro-4-isopropoxypyrimidine, 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, 1250967-81-7, blongs to pyrimidines compound. HPLC of Formula: C7H9ClN2O

To a RT solution of Intermediate 2 (5 mg, 0.01 mmol) in n-BuOH (0.7 mL) were added 2-chloro-4-isopropoxypyrimidine (4 mg, 0.02 mmol) and iPr2NEt (9 pL, 0.05 mmol). The reaction was stirred at 180 C for 80 min, then was cooled to RT. THF (0.8 mL)/MeOH (0.4 mL)/H20 (0.4 mL) were added to the reaction mixture, followed by LiOH.H20 (3 mg, 0.07 mmol) at RT. The reaction was stirred at RT overnight, then was concentrated in vacuo and the residue was diluted with H20 (5 mL). The pH of the mixture was adjusted with aq. IN HC1 to ~5 and it was extracted with EtOAc (3 x 5 mL). The combined organic extracts were washed with brine (2 mL), dried (MgS04) and concentrated in vacuo. The crude product was purified by preparative LC/MS: Column: Waters XBridge C18, 19 x 200 mm, 5-mha 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: 15-55% B over 20 min, then a 4-min hold at 100% B; Flow rate: 20 mL/min. Fractions containing the desired product were combined and concentrated via centrifugal evaporation to provide the title compound (6.5 mg, 8.7 pmol, 67 % yield). LCMS, [M+H]+ = 482.3. NMR (500 MHz, DMSO-de) d 8.42 (s, 1H), 8.06 (br s, 1H), 7.93 (s, 1H), 6.23 (br d, J=6.l Hz, 1H), 5.26 – 5.16 (m, 1H), 5.06 (br s, 2H), 4.84 – 4.77 (m, 1H), 3.92 (s, 3H), 2.68 – 2.60 (m, 1H), 2.42 (s, 3H), 2.06 – 1.44 (m, 8H), 1.22 (d, J=6.l Hz, 6H). hLPAi IC50 = 29 nM.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1250967-81-7, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHI, Yan; WANG, Ying; CHENG, Peter Tai Wah; LI, Jun; WALKER, Steven J.; (147 pag.)WO2019/126089; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 3270-97-1, Adding some certain compound to certain chemical reactions, such as: 3270-97-1, name is 2,4-Diamino-6-methoxypyrimidine,molecular formula is C5H8N4O, 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 3270-97-1.

EXAMPLE 3 Preparation of diethyl 6-methoxypyrimidine-2,4-dioxamate monohydrate: 2,4-Diamino-6-methoxypyrimidine (3.78 g) is dissolved in anhydrous pyridine (20 ml) and thereto is added dropwise ethyloxalyl chloride (9.83 g) under ice cooling, and the mixture is stirred at room temperature for one hour. To the reaction mixture is added water, and the mixture is extracted with ethyl acetate. The organic layer is washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting solid is recrystallized from water-ethanol to give title compound (8.8 g) having the following physical properties. m.p. 132-134 C. IR (KBr) nu: 3625, 3530, 3420, 3010, 1740, 1610, 1530, 1475, 1400, 1305, 1210, 1170, 1100, 1050, 1015, 970, 840 cm-1. NMR (DMSO-d6) delta: 11.30 (1H, s), 10.60 (1H, s), 7.03 (1H, s), 4.29 (4H, q), 3,87 (3H, s), 1.30 (3H, t), 1.25 (3H, t). Elementary analysis: Calcd.: C, 43.58; H, 5.06; N, 15.64 (%). Found: C, 43.75; H, 4.85; N, 15.89 (%).

According to the analysis of related databases, 3270-97-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Toyo Boseki Kabushiki Kaisha; US4729995; (1988); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 87253-62-1, 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. 87253-62-1, name is 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylic acid. A new synthetic method of this compound is introduced below.

General procedure: In 25ml RB flask to a solution of Compound 9 (200 mg) in dry DMF (5ml), EDCI (250 mg, 1.25eq) and DMAP (130 mg,1eq) were added followed by addition of Sulfonamide (1eq). RM was stirred at RT for 4hrs. Solvent from the reaction mixture was evaporated. To the residue water was added and acidified with 6N HCl, solid precipitated out. Solid was filtered and dried. Crude solid was purified by flash chromatography eluating with 4-8% MeOH/DCM as solvent system to give pure product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,87253-62-1, 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Article; Patil, Vikas; Kale, Manoj; Raichurkar, Anandkumar; Bhaskar, Brahatheeswaran; Prahlad, Dwarakanath; Balganesh, Meenakshi; Nandan, Santosh; Shahul Hameed; Bioorganic and Medicinal Chemistry Letters; vol. 24; 9; (2014); p. 2222 – 2225;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia