Day: August 3, 2021

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. 5399-92-8, name is 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

To a solution of 4-chloro-1H-pyrazolo[3,4-d]pyrimidine 2 (0.1 g, 0.65 mmol) in anhydrous DMF(5 mL ), TEA (0.22 g, 0.65 mmol) was firstly added and stirred at room temperature for 30 min. Then, asolution of benzyl bromide (0.11 g, 0.78 mmol) in anhydrous DMF (5 mL) was added and the mixturewas reacted for 1 h, then KI was added and continue reaction. The reaction mixture was at last dilutedwith water (15 mL), and extracted with ethyl acetate. The organic layer was washed with water andthe organic phase was dried over MgSO4 and concentrated, and the residue was purified by columnchromatography on silica gel using 10:1 petroleum ether/ethyl acetate as eluent to give 6: 65% yield,mp 62-63 C; 1H-NMR (400 MHz, DMSO-d6) delta: 8.91 (s, 1H, CH), 8.53 (s, 1H, CH), 7.26-7.33 (m, 5H,ArH), 5.70 (s, 2H, CH2); 13C-NMR (100 MHz, DMSO-d6) 156.6, 151.3, 150.9, 137.2, 135.1, 129.0, 129.0,128.1, 128.1, 128.0, 106.3, 50.8; IR (KBr, delta, cm-1): 3441, 3090, 2935, 1897, 1756, 1585, 1547, 1479, 1410,1347, 1243, 1174, 1135, 950, 858, 783, 730, 698, 596, 534; HRMS (ESI) calcd. for C12H10ClN4: [M + H]+245.0594, found 245.0584.

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, 5399-92-8, 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine.

Reference:
Article; Li, Yong; Cao, Ting-Ting; Guo, Shanchun; Zhong, Qiu; Li, Cai-Hu; Li, Ying; Dong, Lin; Zheng, Shilong; Wang, Guangdi; Yin, Shu-Fan; Molecules; vol. 21; 6; (2016);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1208901-69-2, 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 1208901-69-2, name is 2,4-Dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine hydrochloride. This compound has unique chemical properties. The synthetic route is as follows.

[0076] To the mixture of 2,4-dichloro-5 ,6,7, 8-tetrahydropyrido[4,3 -d]pyrimidine (2.20 g, 9.15 mmol, HC1 salt) in CH2C12 (30.00 mL) was added dropwise TEA (2.78 g, 27.45 mmol, 3.81 mL) at 0 C. Then the mixture was stirred under N2 at 0 C for 5 mm. To the mixture was added 2-methylpropanoyl chloride (1.17 g, 10.98 mmol, 1.15 mL) at 0 C. The mixture was stirred under N2 at 0 C for 2 h. LCMS showed one main peak of desired product. TLC (petroleum ether/EtOAc=1:1, Rf=0.6) showed one new main spot. The mixture was diluted with CH2C12 (40 mL) and washed with water (40 mLx2), citric acid (10%, 40 mLx3), sat.NaHCO3 (40 mLx2), brine (40 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to afford the title compund (2.50 g, crude) as a light yellow solid which was used in the next step without further purification. ?H NIVIR (400 IVIHz, DMSO-d6) oe 4.67-4.59 (m, 2H), 3.85-3.79 (m, 2H), 3.03-2.99 (m, 2H), 2.89-2.85 (m, 1H), 1.04 (d, J 6.4 Hz, 6H).

According to the analysis of related databases, 1208901-69-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KADMON CORPORATION, LLC; OLSZEWSKI, Kellen; POYUROVSKY, Masha; BARSOTTI, Anthony; KIM, Ji-In; LIU, Kevin; MORRIS, Koi; (143 pag.)WO2016/210331; (2016); A1;,
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Pyrimidine – Wikipedia

Related Products of 22536-61-4, 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.22536-61-4, name is 2-Chloro-5-methylpyrimidine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.

A solution of 2- chloro-5-methylpyrimidine (500 g, 3889 mmol, 1.0 equiv.) in DMF (5 L) was degassed with N2 for 20 min and dppf (108 g, 194 mmol, 0.05 equiv.) and Pd2(dba)3 (178 g, 194 mmol, 0.05 equiv.) were added to the reaction mixture. Zn(CN)2(685 g, 5834 mmol, 1.5 equiv.) was then added, and the reaction mixture was heated at 100 C for 16h. The reaction was quenched with water (5 L) and stirred for 10 min. The reaction mixture was then filtered through a pad of Celite brand filter agent. The filtrate was diluted with water (4 L) and extracted with EtOAc (2 x 4 L). The combined organic layers were washed with brine (4 L), dried over Na2SO4,filtered and concentrated under reduced pressure to give the initial product which was further purified by column chromatography using silica gel (60-120 mesh) and 0-10 % EtOAc in hexanes to obtain Example 468.1 (330 g, 71 %) as an off white solid.1H NMR (400 MHz, DMSO-d6) delta 8.89 (s, 2H), 2.39 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 22536-61-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YANG, Kevin; YEH, Wen-Chen; (700 pag.)WO2018/97945; (2018); A1;,
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Pyrimidine – Wikipedia

Reference of 1142188-60-0, 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 1142188-60-0 as follows.

To a solution of tert-butyl 4-hydroxy-6,8-dihydro-5H-pyrido[3,4-d] pyrimidine-7-carboxylate (16.0 g, 63.7 mmol, 1.00 eq) in DMF (4.00 mL) was added DBU (29.1 g, 191 mmol, 28.8 mL, 3.00 eq) and benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (PYBOP) (39.8 g, 76.4 mmol, 1.20 eq). The mixture was stirred at 25° C. for 1 hour. Benzyl piperazine-1-carboxylate (21.0 g, 95.5 mmol, 18.5 mL, 1.50 eq) was added and the reaction mixture was stirred at 25° C. for 16 hours. The mixture was diluted with ethyl acetate (500 mL) and washed with water (3 400 mL), dried over Na 2SO 4, filtered and concentrated under vacuum. The residue was purified by column chromatography (SiO 2, diethyl ether/ethyl acetate=1:1) to give tert-butyl 4-(4-benzyloxycarbonylpiperazin-1-yl)-6,8-dihydro-5H-pyrido[3,4-d]pyrimid- ine-7-carboxylate (2.00 g, 4.41 mmol, 6.93% yield) as a yellow oil. ESI MS m/z 454.3 [M+H] +.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1142188-60-0, its application will become more common.

Reference:
Patent; Mirati Therapeutics, Inc.; Array BioPharma Inc.; Blake, James F.; Burgess, Laurence E.; Chicarelli, Mark Joseph; Christensen, James Gail; Cook, Adam; Fell, Jay Bradford; Fischer, John P.; Marx, Matthew Arnold; Mejia, Macedonio J.; Savechenkov, Pavel; Vigers, Guy P.A.; Smith, Christopher Ronald; Rodriguez, Martha E.; US2019/144444; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 205672-25-9, name is 4-Amino-5-bromo-2-chloropyrimidine. A new synthetic method of this compound is introduced below., HPLC of Formula: C4H3BrClN3

A solution of 5-bromo-2-chioropyrimidin-4-amine (650 mg, 3.12 mmol), tert-butyl (4-methylpiperidin-4-yl)carbamate (835 mg, 3.90 mmol), and 4-methylmorpholine(411 tL, 3.74 mmol) in NMP (6.25 mL) was stirred in amicrowave reactor for 90 mm at 130 C. The resultingresidue was poured into water (100 mL) and was stirred atRT for 5 mm. The solid formed was filtered oil and driedunder high vacuum for 16 h to give tert-butyl (1 -(4-amino-5-bromopyrimidin-2-yl)-4-methylpiperidin-4-yl)carbamate(880 mg, 2.28 mmol). MS mlz 387.3 (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, 205672-25-9, 4-Amino-5-bromo-2-chloropyrimidine.

Reference:
Patent; NOVARTIS AG; Chen, Zhuoliang; Dore, Michael; Fortanet, Jorge Garcia; Karki, Rajesh; Kato, Mitsunori; LaMarche, Matthew J.; Perez, Lawrence Blas; Williams, Sarah; Sendzik, Martin; (63 pag.)US2017/1975; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1820-81-1, 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. 1820-81-1, name is 5-Chlorouracil, molecular formula is C4H3ClN2O2, 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.

5-Chlorouracil (4.5 g, 30.82 mmol) was dissolved in phosphorus oxychloride (100 mL) and phosphorus pentachloride (19.2 g, 92.46 mmol) was added. The reaction mixture was heated at reflux overnight; it was then cooled to RT and the solvent was evaporated under reduced pressure. The residue was cooled to 0 0C and ice flakes were carefully added. The resulting mixture was stirred for 10 minutes; it was then partitioned between water and DCM. The organic phase was separated and washed 3 times with water. The aqueous layers were combined and extracted twice with DCM. The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure to give f> o fQS% vipid) of 2,4, 5-trichloro-pyrimidine as a yellow oil without further purifications.

According to the analysis of related databases, 1820-81-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2008/28860; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 274693-26-4, 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.274693-26-4, name is 2-(((3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol, molecular formula is C26H32F2N6O4S, molecular weight is 562.63, as common compound, the synthetic route is as follows.

2-({(3aR,4S,6R,6aS)-6-[7-{[(1R,2S)-2-(3,4-difluorophenyl)cyclopropyl]amino}-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl]-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxolan-4-yl}oxy)ethanol (VII) in toluene was cooled to 15 to 20 C, Then, 465 g of concentrated hydrochloric acid cooled to 15 to 20 C and 625 g of methanol were added and the reaction mixture was stirred at about 15 to 20 C for about 1 hour. The aqueous solution containing the product was added to 400 g of sodium bicarbonate and water at a temperature below 20 & lt; 0 & gt; C 750 g of the dubbed solution, extracted twice with ethyl acetate, 800 g each time; The organic phases were combined, washed with water, dried over anhydrous sodium sulfate and concentrated. The concentrate was crystallized from a mixed solvent of ethyl acetate / isooctane (720 g / 830 g) to give 169 g of the title compound.

Statistics shows that 274693-26-4 is playing an increasingly important role. we look forward to future research findings about 2-(((3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol.

Reference:
Patent; Sichuan Hai Sike Pharmaceutical Co., Ltd.; Li Xuechao; Luo Jie; Xiang Zhixiang; Yuan Daoyi; (24 pag.)CN103664958; (2017); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 4983-28-2, 2-Chloro-5-hydroxypyrimidine, 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, 4983-28-2, blongs to pyrimidines compound. Application In Synthesis of 2-Chloro-5-hydroxypyrimidine

To a solution of 4-((i?)-l-methanesulfonyloxyethyl)piperidine- 1-carboxylic acid tert- butyl ester (Preparation 114, 1.77g, 5.76mmol) and 2-chloropyrimidin-5-ol (0.75g, 5.75mmol) in NMP (20mL) was added potassium carbonate (l .lg, 8.10mmol) and the reaction was heated to 80°C for 16 h. The reaction mixture was partitioned between TBME and water, and the aqueous layer was separated and washed with further TBME. The organic fractions were combined, washed with water, then brine, and dried (MgS04). Removal of the solvent in vacuo and purification by column chromatography (IH:EtOAc, 100:0 – 70:30) afforded the title compound: 1H NMR deltaEta (400MHz, CDC13): 8.26 (s, 2H), 4.25 – 4.19 (m, 3H), 2.74 – 2.64 (m, 2H), 1.90 – 1.65 (m, 3H), 1.47 (s, 9H), 1.39 – 1.25 (m, 5H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4983-28-2, its application will become more common.

Reference:
Patent; PROSIDION LIMITED; BARBA, Oscar; BELL, James, Charles; DUPREE, Tom, Banksia; FRY, Peter, Timothy; BERTRAM, Lisa, Sarah; FYFE, Matthew, Colin, Thor; GATTRELL, William; JEEVARATNAM, Revathy, Perpetua; KEILY, John; KRULLE, Thomas, Martin; MCDONALD, Russell, Walker; MORGAN, Trevor; RASAMISON, Chrystelle, Marie; SCHOFIELD, Karen, Lesley; STEWART, Alan, John, William; SWAIN, Simon, Andrew; WITHALL, David, Matthew; WO2011/147951; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 211244-81-4, 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.211244-81-4, name is 2-(Methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one, molecular formula is C8H7N3OS, molecular weight is 193.23, as common compound, the synthetic route is as follows.

To 670 mg (3.47 mmol) of 2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (synthesized via procedures found in J. Med. Chem. 2000, 43, 4606-4616) in CH2Cl2 (17 mL) was added 1.55 g (6.93 mmol) of mCPBA and the mixture stirred at ambient temperature for 1 hour. The reaction was concentrated directly and redissolved in dioxane (10 mL). To this solution was added 675 mg (2.25 mmol) of G-2 and 2.4 mL (17.3 mmol) of triethylamine. The reaction was heated to 100 C. for 6 hours. The reaction was cooled to ambient temperature, quenched with saturated NH4Cl and extracted with EtOAc (4×20 mL). The organic phase was dried over MgSO4 and concentrated. The residue was purified by flash column chromatography (EtOAc/hexanes) to afford 0-1 as a solid. Data for O-1: LC/MS: rt=2.01 min; m/z (M+H)=445.4 found; 445.2 required.

The chemical industry reduces the impact on the environment during synthesis 211244-81-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Bergman, Jeffrey M.; Breslin, Michael J.; Coleman, Paul J.; Cox, Christopher D.; Mercer, Swati P.; Roecker, Anthony J.; US2008/132490; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 13223-25-1 ,Some common heterocyclic compound, 13223-25-1, molecular formula is C6H7ClN2O2, 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.

General procedure: To amine (3.0 mmol, 3.0 eq.) in i-PrOH (2.0 mL) was added NEt3(416 muL, 3.0 mmol, 3.0 eq.). To this was added 2-chloro-4,6-dimethoxypyrimidine(174 mg, 1.0 mmol, 1.0 eq.). A greased reflux condenser was attached and themixture heated to reflux (120 C). The reaction was left at this temperatureuntil deemed complete by TLC analysis, typically 6 – 12 h. The reaction wasthen allowed cool to room temperature and then diluted with either EtOAc (10mL, substrates 3 and 4) or Et2O (10 mL, all othersubstrates). This was then washed with water (5 mL). The aqueous phase was thenextracted with the appropriate solvent as previously used (EtOAc or Et2O,3 × 10 mL). The combined organic layers were then washed with brine (10 mL),dried over MgSO4 and then concentrated under reduced pressure toafford the title compound in its crude form. Purification by columnchromatography (silica gel, hexanes:EtOAc, 100:0 ? 60:40) afforded the titlecompound.

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. 13223-25-1, 2-Chloro-4,6-dimethoxypyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Shaw, Julian W.; Barbance, Laure; Grayson, David H.; Rozas, Isabel; Tetrahedron Letters; vol. 56; 35; (2015); p. 4990 – 4992;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia