Pyrimidines

Electric Literature of 62802-38-4, 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.62802-38-4, name is 5-Bromo-2-fluoropyrimidine, molecular formula is C4H2BrFN2, molecular weight is 176.9745, as common compound, the synthetic route is as follows.

[00378] 65A: 2-fluoro-5-(2-fluoro-5-methoxyphenyl)pyrimidine. To a stirred solution of 5-bromo-2-fluoropyrimidine (707 mg, 3.99 mmol) in Toluene (5.0 mL) was added (2- fluoro-5-methoxyphenyl)boronic acid (815 mg, 4.79 mmol), tetrakis(triphenylphosphine) palladium(O) (231 mg, 0.200 mmol) and potassium carbonate (1656 mg, 1 1.98 mmol). The resulting mixture was purged with argon and stirred at 1 10 C for 16h. After cooled to room temperature, the reaction mixture was diluted with water and extracted with DCM. The combined organic extracts were dried over sodium sulfate, filtered and concentrated to give a solid which was purified by chromatography to afford 2-fluoro-5- (2-fluoro-5-methoxyphenyl)pyrimidine (265 mg, 1.169 mmol, 29.3 % yield) as a white solid. LC-MS Anal.Calc’d for CuH8F2N20 222.06, found [M+H] 223.0.

The chemical industry reduces the impact on the environment during synthesis 62802-38-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HERNANDEZ, Andres S.; ELLSWORTH, Bruce A.; EWING, William R.; CHEN, Bin; WO2014/78608; (2014); 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.271-70-5, name is 7H-Pyrrolo[2,3-d]pyrimidine, molecular formula is C6H5N3, molecular weight is 119.124, as common compound, the synthetic route is as follows.COA of Formula: C6H5N3

To 7H-pyrrolo[2,3-d]pyrimidine (6, 0.450 g, 3.78 mmol), N-(2,4-difluoro-3-formyl-phenyl)-4-trifluoromethyl-benzenesulfonamide (10, 1.52 g, 4.16 mmol), and potassium hydroxide (0.689 g, 12.3 mmol), 6.6 mL of methanol was added. The solution was allowed to stir at room temperature for 8 hours, then poured into 50 mL of water and 50 mL of aqueous saturated ammonium chloride and extracted 2*50 mL and 1*25 mL with ethyl acetate. The combined organic layers were washed with water and brine, then dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluding with a gradient of 0-80% ethyl acetate in hexane (with 4% acetic acid) over 15 minutes. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound as a white solid (P-0003, 754 mg). 1H-NMR (dmso-d6) consistent with the desired compound. MS (ESI) [M-H+]-=483.4.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,271-70-5, 7H-Pyrrolo[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Plexxikon, Inc.; US2009/286783; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 3680-69-1 ,Some common heterocyclic compound, 3680-69-1, molecular formula is C6H4ClN3, 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.

4-chloro-7H-pyrrolo[2,3-d]pyrimidine (2-E, 20.0 g, 130.7 mmol) dissolved in DCM (800 mL) was treated portion-wise with N-bromosuccinimide (26.7 g, 149.8 mmol), while maintaining the temperature around 25-30 C. The reaction mixture was stirred at room temperature overnight. Water was added (500 mL) and the phases were separated. The organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The crude product was triturated in Et2O affording after filtration 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine as a white solid (2-F, 22.43 g, 74%). M.p.: 242-244 C.; NMR (400 MHz, DMSO-d6) delta 12.96 (s, 1H), 8.61 (s, 1H), 7.94 (s, 1H); MS m/z 232 [M(35Cl, 79Br)+H]+, 234 [M(35Cl, 81Br)+H]+, 234 [M(37Cl, 79Br)+H]+, 236 [M(37Cl, 81Br)+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3680-69-1, its application will become more common.

Reference:
Patent; ArQule, Inc.; Lapierre, Jean-Marc; Eathiraj, Sudharshan; Namdev, Nivedita; Schwartz, Brian; Ota, Yusuke; Momose, Takayuki; Tsunemi, Tomoyuki; Inagaki, Hiroaki; Nakayama, Kiyoshi; (18 pag.)US9630968; (2017); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 914612-23-0, 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. 914612-23-0, name is 6-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine, molecular formula is C14H14ClN3, 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 ETo a solution of 6-benzyl-4-chloro-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidine (3.9 g, 15.0 mmol) in EtOH (50 mL) was added compound 5 (2.3 g, 15.0 mmol) and DIEA (3.87 g, 30 mmol). The mixture was stirred at 80 C for 3 hours then the mixture was evaporated to dryness. The crude product was purified by silica gel chromatography eluted with PE: EA = (5: 1) to give the desired product (4.08 g)

According to the analysis of related databases, 914612-23-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; COBURN, Craig; WANG, Jiabing; SANTARELLI, Vince; HU, Shuangxi; CUI, Mingxiang; HU, Bin; DONG, Jingchao; LUO, Yunfu; SOLL, Richard, M; WO2011/103715; (2011); 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. 22276-95-5, name is 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below., Safety of 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

To a solution of 5-bromo-4-chloro-7H-pyrrolo[2,3-i Jpyrimidine (40.0 g, 173 mmol) in dry tetrahydrofuran (700 mL) at -78 C was added rc-butyl lithium (195 mL, 2.5 M solution in hexane, 487 mmol) over the period of 2 hours. The reaction mixture was stirred for another 30 minutes at -78 C, after which ethyl chloroformate (17.8 mL, 186mmol) was added over 30 minutes. The reaction mixture was stirred for 2 hours at -60 C and then the temperature was slowly increased to 30 C. The reaction mixture was allowed to stir for 12 hours at 30 C. The progress of the reaction was monitored by TLC using 25% ethyl acetate in petroleum ether using iodine and 254 nm UV light to visualize the spot. The reaction mixture was then quenched with saturated solution of ammonium chloride (200 mL) at 0 C and the reaction mixture was extracted with ethyl acetate (*3). The combined organic layers were washed with water, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford a crude reaction mixture. The residue was purified by chromatography on silica eluting with 5-100% ethyl acetate/petroleum ether to afford ethyl 4-chloro-7H-pyrrolo[2,3-i ]pyrimidine-5- carboxylate as pale yellow solid. LRMS (ESI) calc’d for C9H7C1N302 [M-H]+: 224; found 224. 1H NMR (400 MHz, DMSO-D6): delta 13.28 (s, 1H), 8.70 (s, 1H), 8.39 (s, 1H), 4.31 (q, J= 7.2, 6.8 Hz, 2H), 1.34 (t, J= 7.6, 6.8 Hz, 3H)

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, 22276-95-5, 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; AHEARN, Sean, P.; CHRISTOPHER, Matthew; JUNG, Joon; PU, Qinglin; RIVKIN, Alexey; SCOTT, Mark, E.; WITTER, David, J.; WOO, Hyun Chong; CASH, Brandon; DINSMORE, Christopher; GUERIN, David; WO2013/85802; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 151266-23-8, name is 3-Iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. name: 3-Iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine

[00129] To a mixture of 3-iodo-1 H-pyrazolo[3,4-d]pyrimidin-4-amine (1.044 g, 4 mmol), (4-phenoxyphenyl)boronic acid (0.94 g, 4.4 mmol, 1.1 eq), PdCl2(dppf) (0.29 g, 0.4 mmol, 0.1 eq) and Na2CO3 (0.89 g, 8.4 mmol, 2.1 eq) in a 40 ml reaction vial under vacuum, 25 mL of H20/THF (1 :4) is added via a syringe. The mixture is refilled with N2 and heated to 110 C overnight. TLC showed that the reaction is almost completed. Then solvent is evaporated and the residue is suspended in 200 mL (15% THF/EtOAc) and washed with water, brine, dried over Na2SO4, filtered, and evaporated. The residue is purified with a 50 g silica gel cartridge by Combi-flash (0-10% gradient of methanol in DCM to afford 513 mg of 3-(4-phenoxyphenyl)-1 H-pyrazolo[3,4-d]pyrimidin-4-amine. 1HNMR (300 MHz, DMSO-d6): delta 8.22 (s, 1 H), 7.66 (d, 2 H), 7.43 (t, 2 H), 7.10- 7.23 (m, 5 H).

With the rapid development of chemical substances, we look forward to future research findings about 151266-23-8.

Reference:
Patent; BETA PHARMA CANADA INC.; WANG, Zhaoyin; LI, Lianhai; WANG, Zhigang; WO2013/113097; (2013); 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. 1193-24-4, name is 4,6-Dihydroxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C4H4N2O2

General procedure: According to the conventional manufacturing method of the present inventors [16], under the condition containing two equivalents of triethylamine in dichloromethane at 25 , 4,6- dihydroxy-pyrimidine with 2 equivalents of Compound 2 by acylating a new and compounds 4, 6-pyrimidyl di (2-halo-benzoate) (compound 3) is prepared. After evaporation of dichloromethane, the mixture is dissolved in anhydrous THF, to remove the triethylamine hydrochloride by filtration. The concentrated residue was purified by short length silica gel (Davisil, pH = 7) was purified by column chromatography, or the Compound 3 is prepared by purification was recrystallized with 75% EtOAc / n- hexane

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, 1193-24-4, 4,6-Dihydroxypyrimidine.

Reference:
Patent; Duksung Women’s University Academic Cooperation; Lee, Jae In; Song, Yun jU; Choe, Jin Son; (12 pag.)KR2015/106483; (2015); A;,
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. 58536-46-2, name is 4-(4-Bromophenyl)-2,6-diphenylpyrimidine, molecular formula is C22H15BrN2, 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. category: pyrimidines

Add intermediate IF-1 (12.18g, 31.45mmol) to a 250mL three-necked flask containing THF (100mL), and add n-butyllithium (1.99g, 31.09mmol) dropwise at -78 C. After the dropwise addition, the temperature is maintained for 1h. Trimethyl borate (4.61 g, 44.42 mmol) was then added dropwise, and the temperature was kept at room temperature for 1 h, followed by stirring overnight; hydrochloric acid (2 mol / L) was added to adjust the pH to neutral,After filtration, a white crude product was obtained, which was slurried with n-heptane to obtain a white solid intermediate I-F (7.68 g, yield 70%).

With the rapid development of chemical substances, we look forward to future research findings about 58536-46-2.

Reference:
Patent; Shanxi Laite Optoelectric Materials Co., Ltd.; Ma Tiantian; Yang Min; Nan Peng; (69 pag.)CN110615759; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 147118-40-9, 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.147118-40-9, name is Rosuvastatin methyl ester, molecular formula is C23H30FN3O6S, molecular weight is 495.56, as common compound, the synthetic route is as follows.

The fraction obtained in preparative HPLC is evaporated under reduced pressure (ca 200 mbar) to 50 ml and coled in freezer (ca -20°C) for 3 days. The suspension is filtered. The obtained crystals are dried under vacuum at 40 °C for 5 hours yielding 0,57 g of dry product, containing ca 11 percent of enantiomer; The fraction obtained in preparative HPLC is evaporated under reduced pressure (ca 200 mbar) to 50 ml and coled in freezer (ca -20°C) for 3 days. The suspension is filtered. The obtained crystals are dried under vacuum at 40 °C for 5 hours yielding 0,57 g of dry product, containing ca 11 percent of enantiomer; The filtrate of previous step is evaporated under reduced pressure and dried under vacuum at 40 °C for 5 hours yielding 0,43 g of dry product, containing less than 0,1percent of 3S, 5R enantiomer. The product is enantimerically pure MER having 99,9 percent enantiomeric purity, , as shown on Fig.4

The chemical industry reduces the impact on the environment during synthesis 147118-40-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; LEK Pharmaceuticals d.d.; EP2022784; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 7752-82-1, 5-Bromopyrimidin-2-amine, 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, Safety of 5-Bromopyrimidin-2-amine, blongs to pyrimidines compound. Safety of 5-Bromopyrimidin-2-amine

Example 9; 211 212 213Part A:To compound 211 (1.00 g, 5.74 mmol) in ethanol (100 ml_) was added chloroacetaldehyde (50 wt% solution in water, 7.34 ml_, 57.5 mmol) at room temperature. The reaction mixture was heated at reflux for 16 hours at which time LC- MS analysis indicated that the reaction was complete. The reaction mixture was concentrated under vacuum. The residue was taken back up in ethyl acetate and saturated sodium bicarbonate. The organic and aqueous layers were separated. The organic layer was washed with brine, dried over anh. sodium sulfate and concentrated to afford compound 212 as a beige solid. 1H NMR (400 MHz, DMSO-d6) delta 9.32 (d, 1 H), 8.56 (d, 1 H), 7.85 (d, 1 H), 7.74 (d, 1 H).

The synthetic route of 7752-82-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2008/82487; (2008); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia