Month: March 2022

Adding a certain compound to certain chemical reactions, such as: 1266343-30-9, 5-Bromo-4-chloro-7-methyl-7H-pyrrolo[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, Recommanded Product: 5-Bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, blongs to pyrimidines compound. Recommanded Product: 5-Bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine

5-bromo- 7-meth yl- 7H-p yrrolo[2, 3-d ID yrimidin-4-amineA suspension of 5-bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (17 g, 69.0 mmol) in ammonium hydroxide (150 ml_, 3852 mmol) was stirred for 2 days at 100 C in a sealed vessel. The reaction was allowed to cool to room temperature and filtered. The collected solid was washed with Et20 to afford the product 5-bromo-7-methyl-7H-pyrrolo[2,3- d]pyrimidin-4-amine (12.5 g) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1266343-30-9, 5-Bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE LLC; AXTEN, Jeffrey, Michael; GRANT, Seth, Wilson; HEERDING, Dirk, A.; MEDINA, Jesus, Raul; ROMERIL, Stuart, Paul; TANG, Jun; WO2011/119663; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 289042-10-0, N-(5-((Diphenylphosphoryl)methyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide, 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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

40.0 g of compound (DPPO) and 500 ml of THF were added to a 1000 ml four-necked flask.Stir and dissolve, and replace with nitrogen three times.Under nitrogen protection, the internal temperature was lowered to -75.0 C, and 79.0 ml of 1.0 M NaHMDS/THF solution was slowly added dropwise.Control the internal temperature -80.0 C ~ -75.0 C, after the completion of the addition of the reaction, 2.0 h,After the end of the heat preservation reaction, the internal temperature is controlled from -80.0 C to -75.0 C.The compound (D7) THF solution (D7: 23.1 g, THF: 20 ml) was added dropwise, and the reaction was kept for 1.0 h after the dropwise addition;The sample was controlled until the residual of the compound (DPPO) in the reaction solution was ?1.0%, and the reaction was completed. Rise to room temperature,The reaction was quenched by adding 100 ml of a saturated ammonium chloride solution. After quenching, the material was subjected to distillation under reduced pressure at an external temperature of 50.0 C.Vacuum degree ? -0.09MPa, after evaporation to dryness, add 400.0g of toluene to dissolve,It was washed with water, concentrated, and crystallized from 400.0 g of methanol to give compound (R1) 30.0 g.

The synthetic route of 289042-10-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang Yongtai Pharmaceutical Co., Ltd.; Wang Xuejin; Xu Xubing; Zhang Chong; Chen Hao; (18 pag.)CN109824606; (2019); A;,
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. 919278-72-1, name is 5-Methyl-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one. A new synthetic method of this compound is introduced below., Product Details of 919278-72-1

A mixture of 5-methyl-5H-pyrrolo [3, 2-d]pyrimidin-4-ol(489 mg, 3.28 mmol), 1- (bromomethyl) -4-nitrobenzene (1.06 g, 4.92 mmol), potassium carbonate (1.36 g, 9.84 mmol), sodium iodide (98.3 mg, 0.656 mmol) and N,N-dimethylformamide (7 mL) was stirred at 500C for 15 hr. The reaction mixture was diluted with water, and extracted with ethyl acetate (chi3) . The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (ethyl acetate/hexane=30/70->100/0) to give the title compound (489 mg, 52%) as a yellow solid. 1H-NMR (DMSO-ds, 300 MHz) delta 3.98 (3H, s) , 5.30 (2H, s) , 6.35 -6.36 (IH, m) , 7.41 (IH,- d, J = 2.7 Hz), 7.54 (2H, d, J = 8.9Hz), 8.20 (2H, d, J = 8.9 Hz), 8.29 (IH, s) .

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, 919278-72-1, 5-Methyl-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2007/4749; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 60186-89-2, Adding some certain compound to certain chemical reactions, such as: 60186-89-2, name is 4-Bromo-2,6-dimethoxypyrimidine,molecular formula is C6H7BrN2O2, 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 60186-89-2.

Into a 1-L 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 4-bromo-2,6-dimethoxypyrimidine (23 g, 105.01 mmol, 1 equiv), tetrahydrofuran (250 mL), Diethyl ether (250 mL). And n-BuLi(2.5M) (46.2 mg, 0.72 mmol, 1.10 equiv) was added dropwise at -78 C. After stirred for 5 min at -78 C, ethyl 2,2,2-trifluoroacetate (16.4 g, 115.43 mmol, 1.10 equiv) was added dropwise. After stirred for 30 min at -78 C, the resulting solution was stirred for overnight at RT. The reaction was then quenched by the addition of 200 mL of saturated NH4CI. Sodium carbonate was employed to adjust the pH to 8. The resulting solution was diluted with 1 L of EA. The resulting mixture was washed with 3×500 mL of brine. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 : 100- 1 : 10). The collected fractions were combined and concentrated under vacuum. This resulted in 15 g (56%) of the title compound as an off-white solid. Analytical Data: LC-MS: (ES, m/z): RT = 0.739 min, LCMS 32: m/z = 255 [M+l].

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. 60186-89-2, 4-Bromo-2,6-dimethoxypyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; DUNCAN, Kenneth William; FOLEY, Megan Alene; HARVEY, Darren Martin; KUNTZ, Kevin Wayne; MILLS, James Edward John; MUNCHHOF, Michael John; (586 pag.)WO2017/181177; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 31462-58-5, 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.31462-58-5, name is 5-Iodopyrimidine, molecular formula is C4H3IN2, molecular weight is 205.9845, as common compound, the synthetic route is as follows.

General procedure: A mixture of parthenolide (1.0mmol) and an appropriate aromatic iodide (1.1mmol) was refluxed at 80C using palladium (II) ferrocene (0.01mmol) and di-isopropylethyl-amine (3.0mmol) in toluene (0.1ml) under air for 18-24h. The reaction mixture was then allowed to cool to room temperature, water (8ml) added, and the resultant mixture was extracted with ethyl acetate (10ml×3). The separated organics were dried over Na2SO4, filtered and the filtrate concentrated under reduced pressure. The obtained crude residue was purified by silica flash chromatography (9:1 to 4:1, hexanes/EtOAc) to afford the corresponding aryl substituted parthenolide as a solid (40-50mg) in 70-80% yield.

Statistics shows that 31462-58-5 is playing an increasingly important role. we look forward to future research findings about 5-Iodopyrimidine.

Reference:
Article; Penthala, Narsimha R.; Bommagani, Shobanbabu; Janganati, Venumadhav; Macnicol, Kenzie B.; Cragle, Chad E.; Madadi, Nikhil R.; Hardy, Linda L.; Macnicol, Angus M.; Crooks, Peter A.; European Journal of Medicinal Chemistry; vol. 85; (2014); p. 517 – 525;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 890094-38-9 , The common heterocyclic compound, 890094-38-9, name is 2-Chloro-N-isopropyl-5-nitropyrimidin-4-amine, molecular formula is C7H9ClN4O2, 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: The reaction of 2,4-dichloro-5-nitropyrimidine withisopropylamine produced intermediate 2-chloro-N-isopropyl-5-nitropyrimidin-4-amine. 4-Fluoronitrobenzene reacted with1-methylpiperazine in DMSO yielded the intermediate 1-methyl-4-(4-nitrophenyl)piperazine in the presence of K2CO3. The catalytichydrogenation of 1-methyl-4-(4-nitrophenyl)piperazine with palladiumon carbon (Pd/C, 5%) quantificationally provided thedesired 4-(4-methylpiperazin-1-yl) aniline. Refluxing of the 2-chloro-N-isopropyl-5-nitropyrimidin-4-amine with 4-(4-methylpiperazin-1-yl)aniline in n-butanol yielded N4-isopropyl-N2-(4-(4-methylpiperazin-1-yl)phenyl)-5-nitropyrimidine-2,4-diamine,which was reduced to intermediate A1 with a good yield by catalytichydrogenation using Pd/C as a catalyst. Intermediates A wereprepared as these steps and used for the next step without furtherpurification. These processes were carried out as reported

The synthetic route of 890094-38-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hei, Yuan-Yuan; Shen, Ying; Wang, Jin; Zhang, Hao; Zhao, Hong-Yi; Xin, Minhang; Cao, Yong-Xiao; Li, Yan; Zhang, San-Qi; Bioorganic and Medicinal Chemistry; vol. 26; 8; (2018); p. 2173 – 2185;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 3438-61-7, 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. 3438-61-7, name is 5-Amino-4-methylpyrimidine, molecular formula is C5H7N3, 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.

225.0 g (2.06 mol) of 4-methyl-5-aminopyrimidine was dissolved in 10.0 L of anhydrous THF in a dry flask under nitrogen blanket. The solution was cooled to -200C. 2.0 L (1.39 kg, 5.00 mol) of 2.5 M «-BuLi in hexane was added in 20 minutes while the temperature was kept below -50C. The mixture was agitated at below -15C for 30 minutes and then warmed up to normal room temperature (RT) and stirred for 3 hours. 250.0 g (0.61 mol) of the above methyl ester from stage 7, in 250 mL of anhydrous THF, was added over 25 minutes while the temperature was kept below 350C. The light yellow slurry turned to a dark solution. The solution was stirred for 20 minutes. A reaction sample was quenched with MeOH and analyzed by HPLC to make certain that there is no starting methyl ester left. The solution was then cooled back to below 150C. 2.0 L of MeOH was added over 10 minutes while the temperature was kept below 250C followed by 1.0 L of water added in one portion and the mixture was allowed to warm up to room temperature and stir for 15 hours. A reaction sample was analyzed by HPLC to make certain all related intermediates have been converted. The mixture was cooled to below 200C. 1.2 L of 6 N hydrochloric acid was added over 35 minutes while the temperature was kept below 250C. The solution was agitated for 1 hour. The reaction was monitored by HPLC to make certain that all related intermediates had been converted. The solution was cooled to below 150C. 6 N of NaOH was added to adjust the solution pH to 7-8 (about 370 mL was needed). Most solvents (14.5 L) were removed under vacuum (140 mmHg) and 4.0 L of EtOAc and 2.0 L of water were added. Layers were separated and the organic layer was washed with three 2.0 L portions of water and 1.0 L of brine. The solvent was removed under vacuum from the organic layer to yield 450.0 g of a thick dark brown oil as the crude product. The residue was chased with 500 mL of «-propanol to get 393.2 g of a thick slurry. 500 mL of «-propanol was added and the mixture was heated up to 600C to dissolve the solid. The solution was cooled down with agitation and the slurry was filtered after 16 hours at room temperature and the solid was washed with the filtrate and two 100 mL portions of n- propanol and two 200 mL portions of hexane and air dried to yield the title compound (R)- 1,1,1 -trifluoro-4-(5-fluoro-2-methylphenyl)-4-methyl-2-(5H-pyrrolo[3,2-rf]pyrimidin-6- ylmethyl)pentan-2-ol «-propanol solvate as a light yellow solid, 140.2 g, 44% yield.

According to the analysis of related databases, 3438-61-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2009/134737; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 81765-97-1 ,Some common heterocyclic compound, 81765-97-1, molecular formula is C11H11ClN2S, 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 the solution of 4-amino-2-fluorophenol (41 mg, 0.32 mmol) in dried DMF (3 mL), was added NaH (13 mg, 0.54 mmol). The mixture was stirred at 0 °C for 10 min, and then a solution of 4-chloro-5-(4-fluorophenyl)thieno[2,3-d]pyrimidine 4i (50 mg, 0.19 mmol) in dried DMF (1 mL) was added. The mixture was stirred at 0 °C for 1.5 h. Ice water (5 mL) was added to quench the reaction and the mixture was extracted by Et2O (3 .x. 10 mL). The organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure to obtain the crude product, which was purified by silica gel column chromatograph.

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. 81765-97-1, 4-Chloro-2-methyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhao, Ailing; Gao, Xin; Wang, Yuanxiang; Ai, Jing; Wang, Ying; Chen, Yi; Geng, Meiyu; Zhang, Ao; Bioorganic and Medicinal Chemistry; vol. 19; 13; (2011); p. 3906 – 3918;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1801-06-5, 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 1801-06-5, name is 4-Chloro-5-fluoro-2-methoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

The 32.5g formula III compound are added 170g10wt percent of the isopropyl alcohol solution of ammonia, heating to 40-60°C, stirring reaction 3-5 hours, natural cooling to room temperature, filtered, collecting solid, washing with isopropyl alcohol, drying, the compound of formula II is obtained (kind of white solid) 27.2g, molar yield is 95.0percent, HPLC purity of 99.0percent.

According to the analysis of related databases, 1801-06-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Dixinuo Chemical Pharmaceutical Co., Ltd; Shanghai Desano Pharmaceutical Co., Ltd.; Li, Jinliang; Zhao, Nan; Hua, Sikai; (6 pag.)CN105272922; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 66522-06-3, 4-(tert-Butyl)-2-chloropyrimidine, 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, HPLC of Formula: C8H11ClN2, blongs to pyrimidines compound. HPLC of Formula: C8H11ClN2

To a solution of Intermediate 3 (5 mg, 0.014 mmol) in n-BuOH (0.5 mL) was added 4-(tert-butyl)-2-chloropyrimidine (4 mg, 0.021 mmol) and iPr2NEt (5 pL, 0.028 mmol) at RT. The mixture was heated in a microwave reactor at 180 C for 90 min, then was cooled to RT. To the reaction mixture was added THF (0.8 mL)/H20 (0.4 mL)/MeOH (0.4 mL) and LiOH.H20 (3 mg, 0.070 mmol), and the mixture was stirred at RT overnight. Volatiles were removed in vacuo and the residue was diluted with H20 (5 mL), and then the mixture was adjusted with 1N aq. HC1 to pH ~5 and extracted with EtOAc (3 x 5 mL). The combined organic extracts were washed with brine (2 mL), dried (MgSCL) and concentrated in vacuo. The crude product was purified by preparative LC/MS (Column: Waters XBridge Cl 8, 19 x 200 mm, 5-pm 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: 50-90% B over 20 min, then a 5 min hold at 100% B; Flow: 20 mL/min) to provide the title compound (5.3 mg, 10.7 pmol, 77 % yield). LCMS, [M + H]+ = 480.1. NMR (500 MHz, DMSO-de) d 8.18 (d, ,7=4.3 Hz, 1H), 7.82 (d, ,7=8.5 Hz, 1H), 7.49 (d, J=92 Hz, 2H), 6.62 (d, ,7=4.6 Hz, 1H), 4.97 (br. s., 2H), 4.79 – 4.72 (m, 1H), 4.10 (s, 3H), 2.60 – 2.53 (m, 3H), 2.43 (s, 3H), 2.00 – 1.43 (m, 10H), 1.08 (br. s., 9H). hLPAi IC5o = 26 nM.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,66522-06-3, 4-(tert-Butyl)-2-chloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHI, Yan; WANG, Ying; CHENG, Peter Tai Wah; SHI, Jun; TAO, Shiwei; CORTE, James R.; FANG, Tianan; LI, Jun; KENNEDY, Lawrence J.; KALTENBACH, III, Robert F.; JUSUF, Sutjano; (316 pag.)WO2019/126093; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia