Day: March 24, 2022

Application of 34253-03-7 ,Some common heterocyclic compound, 34253-03-7, molecular formula is C6H6N2O2, 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 methyl pyrimidine-2-carboxylate (25 g, 181 mmol, 1 equiv) in MeOH (500 mL) was added NaBHt (8.2 g, 217 mmol, 1.2 equiv) at 0C. The reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was quenched with H2O (20 mL), concentrated in vacuo and the residue was purified by flash column chromatography (eluted with PE/EtOAc = 1/1) to afford the title compound pyrimidin-2- ylmethanol as a yellow oil (16 g, 80% yield). LC-MS : m/z 111.0 (M+H)+

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. 34253-03-7, Methyl pyrimidine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ANNAPURNA BIO INC.; TANG, Haifeng; BOYCE, Sarah; HANSON, Michael; NIE, Zhe; (213 pag.)WO2019/169193; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 33630-25-0, 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. 33630-25-0, name is 2-Phenylpyrimidin-4-amine. A new synthetic method of this compound is introduced below.

General procedure: A solution of acyl azide 10 (0.640 g, 2.14 mmol) in anhydrous toluene (30 mL) was heated at 100 °C for 45 min. After cooling, the solution was divided equally between three sealed tubes and anilines 13, 14 and 15 (1.42 mmol, 2 equiv) added to the appropriate sealed tube. The tubes were re-capped and heated to 100 °C for a further 2 h. After cooling the toluene was evaporated and the residue purified by flash column chromatography (1:1 hexane/EtOAc to neat EtOAc gradient containing 2.5percent by volume Et3N) to furnish the ureas 17, 18 and 19.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,33630-25-0, 2-Phenylpyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Article; Djung, Jane F.; Mears, Richard. J.; Montalbetti, Christian A.G.N.; Coulter, Thomas S.; Golebiowski, Adam; Carr, Andrew N.; Barker, Oliver; Greis, Kenneth D.; Zhou, Songtao; Dolan, Elizabeth; Davis, Gregory F.; Bioorganic and Medicinal Chemistry; vol. 19; 8; (2011); p. 2742 – 2750;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1250967-81-7, 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.1250967-81-7, name is 2-Chloro-4-isopropoxypyrimidine, molecular formula is C7H9ClN2O, molecular weight is 172.61, as common compound, the synthetic route is as follows.

To a 0C solution of Intermediate 1E (10 mg, 0.026 mmol) and 2-chloro-4- isopropoxy- pyrimidine (7 mg, 0.04 mmol) in DMF (0.3 mL) was added NaH (2 mg of a 60% dispersion in mineral oil, 0.05 mmol). The reaction mixture was stirred at RT for 1 h. LCMS indicated the formation of the two products. Water (0.4 mL) and MeOH (0.4 mL) were added to the reaction mixture, which was stirred for another 1 h at RT, then was concentrated in vacuo. The residue was diluted with H20 (1 mL) and the pH was adjusted with 1N aq. HC1 to ~5, then was extracted with EtOAc (3 x 2 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: XBridge Cl 8, 19 x 200 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 27 min, then a 3-min hold at 100% B; Flow: 20 mL/min). Fractions containing the desired product were combined and dried via centrifugal evaporation. The first eluting isomer was further purified by preparative LC/MS (Column: XBridge Shield RP18, 19 x 200 mm, 5-pm particles; Mobile Phase A: 5:95 MeCN:H20 with l0-mM aq. NH4OAc; Mobile Phase B: 95:5 MeCN:H20 with lO-mM aq. NH4OAc; Gradient: 21-46% B over 25 min, then a 2-min hold at 46% B; Flow: 20 mL/min) to give Example 249 (1.8 mg, 15% yield). Its estimated purity by LCMS analysis was 100%. LCMS, [M + H]+ = 483.4. NMR (500 MHz, DMSO-^e) d 8.28 (d, = 5.6 Hz, 1H), 7.84 (s, 1H), 7.51 (s, 1H), 6.53 (d, J= 5.6 Hz, 1H), 6.02 (s, 2H), 5.09 (p, J= 6.2 Hz, 1H), 4.72 (s, 1H), 4.11 (s, 3H), 2.26 (s, 3H), 1.96 – 1.41 (m, 8H), 1.25 (d, J= 6.2 Hz, 6H; the proton a to the carboxylic acid is not observed due to water suppression). hLPAi IC50 = 67 nM. The second eluting isomer was further purified by preparative LC/MS (Column: XBridge C18, 19 x 200 mm, 5-pm particles; Mobile Phase A: 5:95 MeCN:H20 with 10- mM aq. NH4OAc; Mobile Phase B: 95:5 MeCN:H20 with l0-mM aq. NH4OAc; Gradient: 10-50% B over 27 min, then a 5-min hold at 100% B; Flow: 20 mL/min) to give Example 250 (1.1 mg, 9% yield; 100% purity by LC/MS). LCMS [M + H]+ = 483.1. NMR (500 MHz, DMSO-i/e) d 8.28 (d, J= 5.7 Hz, 1H), 7.86 (d, J= 8.5 Hz, 1H), 7.51 (d, j= 8.7 Hz, 1H), 6.50 (d, j= 5.7 Hz, 1H), 6.00 (s, 2H), 5.18 – 5.07 (m, 1H), 4.72 (s, 1H), 4.11 (s, 3H), 2.26 (s, 3H), 1.91 – 1.43 (m, 8H), 1.18 (d, j= 6.2 Hz, 6H; the proton a to the carboxylic acid is not observed due to water-suppression). hLPAi IC50 = 41 nM.

Statistics shows that 1250967-81-7 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-4-isopropoxypyrimidine.

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

Application of 13566-48-8, Adding some certain compound to certain chemical reactions, such as: 13566-48-8, name is 2-Methyl-4,6-dimethoxypyrimidine,molecular formula is C7H10N2O2, 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 13566-48-8.

4,6-Dimethoxy-2-methylpyrimidine (5 g, 32.4 mmol) was dissolved in 443 carbon tetrachloride (54.1 mL) and 61 N-bromosuccinimide (5.77 g, 32.4 mmol) and 444 azobisisobutyronitrile (0.266 g, 1.622 mmol) were added sequentially to the pressure tube, which was sealed and heated to 80 C. for 4 hours and 100 C. for 16 hours. The reaction vessel was cooled to ambient temperature, concentrated in vacuo, and the resulting crude material was purified via flash chromatography, eluting with 0:100 to 25:75 ethyl acetate:heptanes on a 120 g silica gel column over 20 minutes to provide the 445 title compound. 1H NMR (400 MHz, CDCl3) delta ppm 5.92 (s, 1H), 4.39 (s, 2H), 3.95 (s, 6H); MS (ESI+) m/z 235.0 (M+H)+.

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. 13566-48-8, 2-Methyl-4,6-dimethoxypyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Desroy, Nicolas; Gfesser, Gregory A.; Greszler, Stephen N.; Koenig, John R.; Kym, Philip R.; Liu, Bo; Scanio, Marc J.; Searle, Xenia; Wang, Xueqing; Yeung, Ming C.; Zhao, Gang; (247 pag.)US2018/99932; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 52854-14-5, 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. 52854-14-5, name is 4-Chloro-6-methoxy-5-nitropyrimidine, molecular formula is C5H4ClN3O3, 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.

4-Chloro-6-methoxy-5-nitropyrimidine (0.6g) and 5% Pd on carbon (0.6g) in ethanol(90mL) and under hydrogen (2 bar) was stirred at room temperature for 16h. The mixturewas filtered through a pad of celite and evaporated under reduced pressure to give thesubtitle compound (0.35g).

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 52854-14-5, 4-Chloro-6-methoxy-5-nitropyrimidine.

Reference:
Patent; ASTRAZENECA AB; WO2004/108690; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 186519-92-6 ,Some common heterocyclic compound, 186519-92-6, molecular formula is C7H4ClN3O2, 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 stirred suspension of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid (H-1) (3.11 g, 15.7 mmol, 1.0 eq) and a catalytic amount of DMF in a mixture of DCM (40 mL) and THF (40 mL) at RT, oxalyl chloride (2.0 mL, 23.5 mmol, 1.5 eq) is added dropwise. The resulting mixture is stirred for 2 h and then concentrated in vacuo. The residue is dissolved in DCM (50 mL) and the resulting solution is added dropwise to saturated aqueous ammonium hydroxide (200 mL) at RT. The resulting mixture is stirred for 30 min and then filtered. The filter cake is rinsed with H2O (30 mL*2). The filtrate is acidified with conc. HCl to adjust the pH to 4-5. The solid is collected by filtration, rinsed with water and dried in vacuo to afford the product, 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide (H-2).

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. 186519-92-6, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ren, Pingda; Liu, Yi; Li, Liansheng; Chan, Katrina; Wilson, Troy Edward; Castro, Alfredo C.; Evans, Catherine A.; Snyder, Daniel A.; US2012/122838; (2012); 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. 36314-98-4, name is 2-Amino-4-cyanopyrimidine. A new synthetic method of this compound is introduced below., Recommanded Product: 2-Amino-4-cyanopyrimidine

Step 2: Synthesis of 1-37.2To a solution of 1-37.1 (100 mg, 0.83 mmol) in CH3CN (10 mL) is added NBS (222 mg, 1.2 mmol) at room temperature. The solution is stirred at the same temperature for 12 hours. The solution is concentrated and the residue is purified by silica gel flash column chromatography with 10% MeOH in CH2C12 as the eluent to afford 1-37.2 (100 mg); m/z: 200 [M++l]

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, 36314-98-4, 2-Amino-4-cyanopyrimidine.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BARTOLOZZI, Alessandra; BOSANAC, Todd; CHEN, Zhidong; DE LOMBAERT, Stephane; HUBER, John, D.; LIU, Weimin; LO, Ho Yin; LOKE, Pui Leng; RIETHER, Doris; TYE, Heather; WU, Lifen; ZINDELL, Renee, M.; WO2012/40137; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 83255-86-1 ,Some common heterocyclic compound, 83255-86-1, molecular formula is C5H4BrN5, 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.

Add N, N-dimethylacetamide (50mL) to the reaction flask,Add 4-phenoxybenzoic acid (II) (4.81g, 0.022mol) under nitrogen protection,3-bromo-4-amino-1H-pyrazolo [3,4, d] pyrimidine (III) (4.37 g, 0.02 mol),Sodium carbonate (8.74g, 0.1mol), CuBr (0.43g, 0.003mol), 1,10-phenanthroline (0.73g, 0.004mol). The temperature was raised to 150 C for 24h. The temperature was lowered to room temperature, water was slowly added to precipitate a solid, filtered, and dried to obtain a solid product (4.95 g, yield: 81.5%).

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. 83255-86-1, 3-Bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hangzhou China-USA East China Pharmaceutical Co., Ltd.; Yu Rui; Chen Yu; Wu Honghui; Hu Haiwen; Ye Kai; (6 pag.)CN110511225; (2019); A;,
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 1266343-30-9, name is 5-Bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C7H5BrClN3

Stir a suspension of 5-bromo-4-chloro-7-methyl-pyrrolo[2,3-d]pyrimidine (454 g 1.84 mol) in ammonia (30% in H20, 3.63 L) at 120 C in a Hastelloy pressure vessel for 18 h. Cool to 20 C, filter, wash with H20 (1.80 L) and methanol (900 mL), and dry to give the title compound (351 g, 82%) as a white solid. ES/MS m/z (79Br) 227.2(M+H).

With the rapid development of chemical substances, we look forward to future research findings about 1266343-30-9.

Reference:
Patent; ELI LILLY AND COMPANY; CIFUENTES-GARCIA, Marta Maria; GARCIA-PAREDES, Maria Cristina; (34 pag.)WO2018/194885; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 69785-94-0, 5-Aminopyrimidin-4(3H)-one, 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, 69785-94-0, blongs to pyrimidines compound. COA of Formula: C4H5N3O

Example 62 5-Fluoro-N-(4-hydroxy-5-pyrimidinyl)-2-(3-methylsulfanyl-phenoxy)-nicotinamide 5-fluoro-2-(3-methylsulfanyl-phenoxy)-nicotinic acid (150 mg, 0.54 mmol) was dissolved in dimethylformamide (5 ml) and triethylamine (225 l, 1.61 mmol) was added followed by 3-amino-2-hydroxy-pyrimidine (85 mg, 0.56 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (113 mg, 0.59 mmol) and 1-hydroxybenzotriazole (80 mg, 0.59 mmol). The reaction was stirred under nitrogen at room temperature for 48 h and the solvent was removed under reduced pressure. The residue was partitioned between water (10 ml) and dichloromethane (20 ml) and the aqueous phase was extracted with dichloromethane (2*20 ml). The combined organic extracts were washed with brine (10 ml), dried over MgSO4 and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel using dichloromethane:methanol:ammonia (95:5:0.5) as eluent to give the title compound (80 mg) as an off-white solid. 1H NMR (400 MHz, D6-DMSO): delta=12.85 (1H, brs), 10.43 (1H, brs), 8.90 (1H, s), 8.34 (1H, d), 8.27-8.30 (1H, dd), 8.04 (1H, s), 7.35-7.39 (1H, t), 7.21 (1H, s), 7.14-7.16 (1H, d), 7.04-7.07 (1H, d) ppm. N.B. Suspect peak hidden under DMSO peak 3.52 (3H, s) ppm. LRMS (electrospray): m/z [M+Na]+ 395 and [M-H]- 371. Anal. Found C, 54.76; H, 3.53; N, 14.81. C17H13FN4O3S requires C, 54.83; H, 3.52; N, 15.05%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69785-94-0, its application will become more common.

Reference:
Patent; Pfizer Inc; US2005/20587; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia