Tag: M.W:200-300

Synthetic Route of 26032-72-4 ,Some common heterocyclic compound, 26032-72-4, molecular formula is C10H6Cl2N2, 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.

[00240] To a solution of 2,4-dichloro-6-phenylpyrimidine (1.52 g, 6.7 mmol) and (¡À)-trans-methyl 3-aminobicyclo[2.2.2]octane-2-carboxylate (1.84 g, 10.0 mmol) inN,N-dimethylformamide (10 mL) was added potassium carbonate (0.92 g, 6.7 mmol). The mixture was stirred at rt overnight. After the reaction was completed, the mixture was diluted with H20 (50 mL), and the resulting mixture mixture was extracted with ethyl acetate (40 mL x3). The combined organic layers were washed with saturated brine (50 mL), dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (n-hexane/EtOAc (v/v) = 20/1 – 10/1) to give the title compound as a white solid (1.65 g, 66%).MS (ESI, pos.ion) m/z: 372.2 [M+H]+1H NMR (400 MHz, CDC13) (ppm): 8.04-7.91 (m, 2H), 7.5 1-7.41 (m, 3H), 6.78 (s, 1H), 5.41 (s, 1H), 4.32 (s, 1H), 3.73 (s, 3H), 2.38 (d, J= 5.1 Hz, 1H), 2.07 (s, 1H), 1.86 (m, 1H), 1.73 (m, 1H),1.70-1.60 (m, 4H), 1.57 (m, 2H), 1.5 1-1.41 (m, 1H).

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. 26032-72-4, 2,4-Dichloro-6-phenylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; REN, Qingyun; TANG, Changhua; LIN, Xiaohong; YIN, Junjun; YI, Kai; (270 pag.)WO2017/97234; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 31462-54-1, name is 2-Iodopyrimidine, the common compound, a new synthetic route is introduced below. SDS of cas: 31462-54-1

Compound 2 obtained in the manner described above (200 mg, 0.971 mmoles), 2,5-thiophene diborate (Wako Pure Chemical Industries, Ltd.) (501 mg, 2.91 mmoles), sodium carbonate (Wako Pure Chemical Industries, Ltd.) (309 mg, 2.91 mmoles) and tetrakis (triphenylphosphine) palladium (0) (Wako Pure Chemical Industries, Ltd.) (33.7 mg, 0.0292 mmoles) were dissolved in a mixed solvent containing 10 ml of toluene and 10 ml of methanol. Air was removed to create a vacuum and the space was purged with nitrogen three times after which the reaction mixture was agitated for thirty minutes at 60C. After letting the reaction solution stand until cooled, Compound 1 obtained in the manner described above was added. The air was removed to create a vacuum and the space was purged with nitrogen three times again after which the reaction mixture was agitated for four hours at 60C. After allowing the reaction solution to cool, the reaction solution was diluted with ethyl acetate, washed once using de-ionized water, and once using an aqueous saturated sodium chloride solution. The organic layer was dried using anhydrous sodium sulfate. The solvent was removed by distillation, and the product was purified using a medium pressure fractionating liquid chromatography to obtain yellow solids (Compound 5) (191 mg, 0.453 mmoles, 47%). The analytical results for the Compound 5 synthesized {N,N-dihexyl-4-[5-(pyrimidine-2-yl) thiophene-2-yl] aniline} are shown below. 1H-NMR (400 MHz, CDCl3, TMS, rt) delta 8.67 (2H, d, J = 4.9 Hz), 7.92 (1H, d, J = 3.9 Hz), 7.53 (2H, brd, J = 8.8 Hz), 7.18 (1H, d, J = 3.8 Hz), 7.03 (1H, t, J = 4.9 Hz), 6.64 (2H, brd, J = 8.8 Hz), 3.29 (4H, t, J = 7.7 Hz), 1.60 (4H, brs), 1.33 (12H, brs), 0.91 (6H, t, J = 6.5 Hz)

The synthetic route of 31462-54-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; National University Corporation Hokkaido University; EP2395055; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 187035-79-6, 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 187035-79-6, name is Ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

(S)-(2-(8-(hydroxymethyl)-1-isopropyl-7-(methylsulfonyl)-3,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrazin-2(1H)-yl)-4-(trifluoromethyl)pyrimidin-5-yl)methanol To a solution of (R)-methyl 1-isopropyl-7-(methylsulfonyl)-1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazine-8-carboxylate (80 mg, 0.228 mmol) in iPrOH (2 mL) and DCM (1 mL) was added ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate (174 mg, 0.684 mmol) and DIEA (177 mg, 1.37 mmol). The mixture was stirred at 60 C. overnight. Water (5 mL) was added to the mixture and the aqueous layer was extracted with EtOAc (2*10 mL). The combined organic layers were washed with water (2*10 mL) and brine, dried over anhydrous Na2SO4, filtered and concentrated under vacuum. The residue was purified by preparative TLC to afford (R)-methyl 2-(5-(ethoxycarbonyl)-4-(trifluoromethyl)pyrimidin-2-yl)-1-isopropyl-7-(methylsulfonyl)-1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazine-8-carboxylate (75 mg, 57.8% yield) as a yellow solid.

According to the analysis of related databases, 187035-79-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Vitae Pharmaceuticals, Inc.; Gregg, Richard E.; US2015/250787; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 145783-15-9, 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. 145783-15-9, name is 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine, molecular formula is C7H9Cl2N3S, 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.

Method B: Compound (IX) (150 g, 0.6 mole) (IX was purchased from Shanghai Haoyuan Chemexpress Co., Ltd.) was dissolved in 1.0 L N,N-dimethyl formamide (DMF). Pyridine (69.3 g, 1.0 mole) was added to the solution. The solution was cooled in ice water until the system internal temperature was below 10C. Pentafluorophenyl trifluoroacetate (184.5 g, 0.66 mole) was slowly added dropwise to the solution. After pentafluorophenyl trifluoroacetate was added completely, the solution was allowed to warm naturally to room temperature, and was stirred for 5 h. The reaction was monitored by HPLC. Afier the conversion of the raw material was complete, 2.0 L tap water was added to the reaction solution. The reaction solution was extracted twice with 1 .0 L methyl tertiary-butyl ether. The organic phase was washed with 0.5 L saturated salt water, then dried for not less than 3 h, filtered and concentrated to get 186.2 g compound (VIII) in 93% yield. The resulting product was directly used in the nextstep.

According to the analysis of related databases, 145783-15-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JIANGSU HENGRUI MEDICINE CO., LTD.; SUNCADIA PHARMACEUTICALS CO., LTD.; SUN, Shaoguang; SONG, Defu; HE, Biao; LAI, Xiaobo; (22 pag.)US2016/52928; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 659729-09-6, 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.659729-09-6, name is 4-Chloro-6-(4-(trifluoromethyl)phenyl)pyrimidine, molecular formula is C11H6ClF3N2, molecular weight is 258.63, as common compound, the synthetic route is as follows.

To a mixture of 3 ml of water, 0.36 g of sodium cyanide and 0.07 g of 1, 4-diazabicyclo [2.2.2] octane, 9 ml of dimethyl sulfoxide and 1.6 g of 4-chloro-6- (4- trifluoromethylphenyl) pyrimidine were added at 0C. This mixture was stirred for 2 hours. The reaction mixture was poured into water and then extracted three times with tert- butyl methyl ether. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated to obtain a crude product. This crude product was used in the next step without purification.

The chemical industry reduces the impact on the environment during synthesis 659729-09-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; MIZUNO, Hajime; WO2010/134478; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 62458-96-2, 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. 62458-96-2, name is 7-Benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4(3H)-one. A new synthetic method of this compound is introduced below.

To 7-benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4(3H)-one (Step A, 1.50 g, 6.22 mmol) in toluene (25 mL) were sequentially added DIPEA (0.87 mL, 5.0 mmol) and POCl3 (0.70 mL, 7.46 mmol). The contents were heated at 105 C. for 2 hour, cooled to rt, diluted with dichloromethane (100 mL) and stirred with cold aq. sat’d NaHCO3 (150 mL) for 1 h. The dichloromethane layer was dried over sodium sulfate and concentrated under reduced pressure to afford the title compound b (1.61 g) as a dark oil. LCMS [M+H]+ 260.08.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62458-96-2, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/275052; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 26032-72-4, 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 26032-72-4 as follows.

As shown in Figure 3-step i, a mixture of phenylboronic acid (1.22 g),2,4,6-trichloropyrimidine (compound 1011), tetrakis(triphenylphosphine) palladium(O) and 2N sodium carbonate (15 mL) in DME (25 mL) was heated at 80 0C overnight. After cooling to it, addition of water (30 mL), extraction with dichloromethane (3 x 20 mL), drying and evaporation, purification by column chromatography (SiO2, 10-20% ethyl acetate in hexane) afforded the desired product, 6-phenyl-2,4-dichloropyrimidine (compound 1012) (0.544 g). As shown in Figure 3-step ii, compound 1012 (0.34 g) was mixed with (,S)-2-amino-N-(2,2,2- trifluoroethylpropanamide (0.3 g) and diisopropylethylamine (0.63 mL) in isopropanol (5 mL) and the reaction mixture heated at 80 0C overnight. Evaporation gave a residue, which after aqueous workup and purification (SiO2, 20% ethyl acetate/hexane) produced 2-(2- chloro-6-phenyl-pyrimidin-4-ylamino)-nu-(2,2,2-trifluoro-ethyl)propionamide (compound 1013) (0.165 g). As shown in Figure 3-step iii, compound 1013 (29 mg), 5-(4,4,5,5- Tetramethyl-[l,3,2]dioxaborolan-2-yl)-7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (compound 1005), PdCl2dppf2 (7 mg), and potassium phosphate (32 mg) were heated in 1,4- dioxane (2 mL) at 80 0C overnight. To the reaction was added aqueous lithium hydroxide solution (2 mL). After heating at 600C for Ih, water (20 mL) was added. Extraction with dichloromethane (3X), drying, evaporation and purification (SiO2, 50-100% ethyl acetate/hexane) gave 3.7 mg of 2-[6-phenyl-2-(7eta-pyrrolo[2,3-d]pyrimidin-5-yl)-pyrimidin- 4-ylamino]-N-(2,2,2-trifluoro-ethyl)-propionamide (compound 18).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,26032-72-4, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2007/41130; (2007); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 129872-81-7, 2,4-Dichloro-5-methyl-5H-pyrrolo[3,2-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, Application In Synthesis of 2,4-Dichloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidine, blongs to pyrimidines compound. Application In Synthesis of 2,4-Dichloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidine

General procedure: Pd(PPh3)2Cl2 (23 mg, 0.03 mmol), 4-trifluoromethoxyphenylboronic acid (73 mg, 0.35 mmol), compound 15 (100 mg, 0.32 mmol) and TEA (91 mg, 0.90 mmol) were added to a solution of DMF (5 mL) and H2O (0.5 mL). The mixture was stirred at 80 oC for 4 h. Water (10 mL) and EtOAc (30 mL) were added to the reaction. The layers were separated. The aqueous layer was extracted using EtOAc (10 mL). The combined organic extracts were dried over anhydrous Na2SO4. The solvent was removed under reduced pressure, and the resulting residue was purified via silica gel column chromatography using petroleum ether/EtOAc (5/1) to give 16 (67 mg, 48 %) as a yellow solid.

The synthetic route of 129872-81-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Liandi; Xin, Minhang; Shen, Han; Wen, Jun; Tang, Feng; Tu, Chongxing; Zhao, Xinge; Wei, Ping; Bioorganic and Medicinal Chemistry Letters; vol. 24; 15; (2014); p. 3486 – 3492;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 85979-59-5, Adding some certain compound to certain chemical reactions, such as: 85979-59-5, name is 2-Chloro-4-(4-fluoro-phenyl)-pyrimidine,molecular formula is C10H6ClFN2, 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 85979-59-5.

To a solution of 68 (109 mg, 0.25 mmol) and 2-chloro-4-phenylpyrimidine (77 mg,0.37 mmol) in t-BuOH (3 mL) was added conc. HCI (0.25 mL). The reaction was heatedat 80 C for 8 hours before concentrated under reduced pressure. The residue was dissolved in CH3CN and basified with Et3N. The resulting solution was purified by reverse prep-HPLC and then silica gel prep-TLC to give 3-((4-(4-fluorophenyl)pyrimidin- 2-yl)amino)-4-methyl-N-(3-(4-methyl-1 H-imidazol-1 -yl)-5-(4-methylpiperazin-1 -yl)phenyl)benzenesulfonamide (21 mg, 14%) as an off-white solid.

According to the analysis of related databases, 85979-59-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CARDIO THERAPEUTICS PTY LTD; TREUTLEIN, Herbert; ZENG, Jun; DIXON, Ian; JAMES, Ian; PALMER, James T; (169 pag.)WO2018/165718; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 50593-92-5, Adding some certain compound to certain chemical reactions, such as: 50593-92-5, name is 5-Bromo-2-(methylthio)pyrimidine-4-carboxylic acid,molecular formula is C6H5BrN2O2S, 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 50593-92-5.

(b). 2-Methylsulfanyl-pyrimidine-4-carboxylic acid; The product of example 21a (517 mg) in methanol (25 ml) was hydrogenated in a PARR apparatus in the presence of KOH (260 mg) and 10% Pd on BaSO4 (260 mg) for4 h. The reaction mixture was filtered over decalite and washed with methanol (warm), The filtrate was concentrated to 50% of its volume followed by addition of cone. HCl(33%) to pH 1. The precipitate (KBr) was filtered off and the mother liquor was concentrated in vacuo. The residue was recrystallized from dioxane. Yield: 200 mg. MS-ESI: [M+H]+ = 170

According to the analysis of related databases, 50593-92-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; N.V. ORGANON; WO2006/117368; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia