Pyrimidines

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;,
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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;,
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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;,
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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;,
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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;,
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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;,
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Related Products of 25940-35-6, Adding some certain compound to certain chemical reactions, such as: 25940-35-6, name is Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid,molecular formula is C7H5N3O2, 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 25940-35-6.

To a solution of 5-(5-bromo-2-(difluoromethoxy)phenyl)-l-((2- (trimethylsilyl)ethoxy)methyl)-lH-pyrazol-4-amine (50.1 g, 115 mmol) in DMA (1500 mL) was added pyrazolo[l,5-a]pyrimidine-3-carboxylic acid (32.1 g, 196.0 mmol), PyAOP (102 g, 196 mmol), DMAP (1.41 g, 11.0 mmol) and DIPEA (44.1 g, 0.341 mol). The resulting solution was stirred for 3h at 60C in an oil bath. The reaction was then quenched by the addition of 2000 mL of water/ice. The resulting solution was extracted with 3×2000 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 1×1000 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column eluting with ethyl acetate/petroleum ether (80%). The collected fractions were combined and concentrated under vacuum. The solid was stirred with 150 mL of H20 at rt, and the solid were collected by filtration. Dried in air. This resulted in 60.1 g (91%) of N-(5-(5-bromo-2-(difluoromethoxy)phenyl)-l-((2-(trimethylsilyl)ethoxy)methyl)-lH- pyrazol-4-yl)pyrazolo[l,5-a]pyrimidine-3-carboxamide as a light yellow solid. LCMS (Method G, ESI): [M+H]+= 579.1 & 581.1, RT= 1.10 min. 1H NMR (300 MHz, CDC13): delta (ppm) 9.62 (s, 1H), 8.80 (dd, J = 6.9, 1.7 Hz, 1H), 8.73 (s, 1H), 8.53 (dd, J = 4.2, 1.7 Hz, 1H), 8.38 (s, 1H), 7.79 (d, J = 2.4 Hz, 1H), 7.67 (dd, / = 8.8, 2.5 Hz, 1H), 7.29 (d, / = 1.4 Hz, 1H), 7.00 (dd, / = 6.9, 4.2 Hz, 1H), 6.43 (t, / = 72.6 Hz, 1H), 5.53 – 5.27 (m, 2H), 3.73 – 3.50 (m, 2H), 0.88 (ddd, / = 9.5, 6.4, 4.4 Hz, 2H), 0.00 (s, 9H).

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. 25940-35-6, Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; CHENG, Yun-Xing; GIBBONS, Paul; KELLAR, Terry; LI, Wei; MENDONCA, Rohan; YUEN, Po-wai; ZAK, Mark Edward; ZHANG, Lei; (212 pag.)WO2017/89390; (2017); A1;,
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Electric Literature of 956034-07-4, 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. 956034-07-4, name is 2,4-Dichlorofuro[3,2-d]pyrimidine. A new synthetic method of this compound is introduced below.

Preparation of 2-chloro-4-(3-nitrophenoxy -furo|”3.2- cnpyrimidine6.4 g (33.9 mmol) of 2,4-dichlorofuro[3,2-Patent; HANMI HOLDINGS CO. , LTD.; CHA, Mi Young; KANG, Seok Jong; KIM, Mi Ra; LEE, Ju Yeon; JEON, Ji Young; JO, Myoung Gi; KWAK, Eun Joo; LEE, Kwang Ok; HA, Tae Hee; SUH, Kwee Hyun; KIM, Maeng Sup; WO2011/162515; (2011); A2;,
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Reference of 1722-12-9 , The common heterocyclic compound, 1722-12-9, name is 2-Chloropyrimidine, molecular formula is C4H3ClN2, 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.

To a solution of 2-chloropyrimidine (300 mg, 2.619 mmol) in dioxane (5 ml), was added piperidin-4-one hydrochloride monohydrate (402.3 mg, 2.619 mmol) at room temperature. The mixture was heated at 80 C. overnight and concentrated under reduced pressure. The residue was treated with EtOAc (30 ml) and saturated NaHCO3 (10 ml). After separation of the layers, the aqueous phase was extracted with EtOAc (2×10 ml). The combined organic layers were washed with brine (10 ml), dried (MgSO4), filtered, and concentrated under reduced pressure to furnish a crude product. This material was purified by column chromatography (40% EtOAc/hexanes) to give 1-pyrimidin-2-yl-piperidin-4-one (320 mg, 53%) as an off-white solid: 1H NMR (CDCl3, 400 MHz) delta 8.38 (d, J=6.4 Hz, 2 H), 6.61 (t, J=6.4 Hz, 9 H), 4.16 (t, J=5.6 Hz, 2 H), 2.53 (t, J=5.6 Hz, 2 H).

The synthetic route of 1722-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Barbosa, Joseph; Dong, Li; Fink, Cynthia Anne; Wang, Jiancheng; Zipp, G. Gregory; US2006/258672; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 22536-66-9, 2-Chloropyrimidine-4-carboxamide, 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, name: 2-Chloropyrimidine-4-carboxamide, blongs to pyrimidines compound. name: 2-Chloropyrimidine-4-carboxamide

4.3. 2-[{3-[4-{[5-Methyl-2-(1-methylethyl)phenoxy]methyl}-1-piperidyl]-propyl}amino]pyrimidine-4-carboxamide 4.4 g (0.0144 mol) of 4-{[5-methyl-2-(1-methylethyl)phenoxy]methyl}-1-piperidinepropanamine hydrochloride, 2.27 g (0.0144 mol) of 2-chloropyrimidine-4-carboxamide and 2.98 g (0.0216 mol) of K2 CO3 in 86 ml of DMF are reacted. The mixture is stirred for 48 h. It is poured into water and then extracted 3 times with AcOEt. The organic phase is washed 3 times with water. It is dried over Na2 SO4, filtered and concentrated. The product crystallises. It is taken up in a little ether and the mixture is filtered. 4.5 g (0.0105 mol) of base are obtained, which base is taken up in 100 ml of EtOH and a solution of 1.22 g (0.0105 mol) of fumaric acid in 150 ml of EtOH is added. M.p. 183-88 C. Yield: 36%.

The synthetic route of 22536-66-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Synthelabo; US5210086; (1993); A;,
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Pyrimidine – Wikipedia