Day: January 8, 2021

Application of 37554-70-4, 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. 37554-70-4, name is 2-Chloro-5-fluoro-4-methoxypyrimidine, molecular formula is C5H4ClFN2O, 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-Fluoro-4-methoxypyrimidin-2-yl)phenylamine; To a stirred solution of 2-chloro-5-fluoro-4-methoxypyrimidine (16.0 g, 98.8 mmol) and phenylamine (13.8 g, 141.8 mmol) in 1,4-dioxane (500 ml) was added Cs2CO3 (97.8 g, 296.3 mmol) followed by Pd2(dba)3 (2.7 g, 2.9 mmol) and BINAP (3.1 g, 4.9 mmol) under N2. The mixture was heated at reflux for 12 h. On completion, the mixture was filtered to remove the inorganic salts and the filtrate was partitioned between CH2Cl2 (500 ml) and H2O (500 ml). The CH2Cl2 layer was washed with brine (500 ml), dried over NaSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with 5% EtOAc/PE, to afford 13.0 g (63% yield) of the product as a yellow solid.1H NMR (400 MHz, CDCl3) delta 8.07 (d, J = 2.8 Hz, 1H), 7.61 (d, J = 8.0 Hz, 2H), 7.34 (m, 2H), 7.16 (br s, 1H), 7.07 (m, 1H), 4.06 (s, 3H).

According to the analysis of related databases, 37554-70-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wada, Hiroki; Cheng, Lili; Jiang, Ji; Jiang, Zhigan; Xie, Jun; Hu, Tao; Sanganee, Hitesh; Luker, Tim; Tetrahedron Letters; vol. 53; 14; (2012); p. 1720 – 1724;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 36315-01-2, 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.36315-01-2, name is 2-Amino-4,6-dimethoxypyrimidine, molecular formula is C6H9N3O2, molecular weight is 155.16, as common compound, the synthetic route is as follows.

General procedure: For the synthesis of 2, the solution of sulfurisocyanatidic chloride (7.2mmol) in 20mL toluene was added to the solution of 1 (6.0mmol) in 20mL toluene dropwise at room temperature. The reactant was heated to 140C and then the reaction proceeded for 18h under reflux. Subsequently, the mixture was cooled down to room temperature and remaining sulfurisocyanatidic chloride was removed under reduced pressure, together with the solvent. Without further purification, the resulting yellow oil 2 was dissolved in 10mL anhydrous acetonitrile and after that it was added slowly to 5mmol of 3, which was also dissolved in 10mL anhydrous acetonitrile beforehead in ice bath. After stirring for 24hat room temperature, acetonitrile was removed under reduced pressure and saturated sodium bicarbonate was added to product 4. Product 5 precipitated easily and it was further purified by recrystallization from petroleum ether/acetone in 1:1 ratio in high yields. 15% hydrochloric acid was added to aqueous solution of 5 under stirring and corresponding acidified product 4 precipitated out easily in high yields.

The chemical industry reduces the impact on the environment during synthesis 36315-01-2, I believe this compound will play a more active role in future production and life.

Reference:
Article; Wu, Ren-Jun; Ren, Tongtong; Gao, Jie-Yu; Wang, Li; Yu, Qilin; Yao, Zheng; Song, Guo-Qing; Ruan, Wei-Bin; Niu, Cong-Wei; Song, Fu-Hang; Zhang, Li-Xin; Li, Mingchun; Wang, Jian-Guo; European Journal of Medicinal Chemistry; vol. 162; (2019); p. 348 – 363;,
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 24415-66-5, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine

Adding 85 mg (about 0.5 mmol) to a 10 mL microwave reaction tube.7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, 198 mg (about 1.5 mmol) of N-methylindole, 14 mg (about 10 mol%) of the catalyst bistrifluoromethylsulfonimide and 1 mL of the solvent HFIP, and then the microwave reaction tube was sealed.Then, the reactant in the microwave reaction tube was stirred at 100 C for 6 hours, and the solvent was distilled off under reduced pressure.And purified by column chromatography using DCM/MeOH as eluent to give about 89 mg of pure product e12 as a yellow solid.67%;

With the rapid development of chemical substances, we look forward to future research findings about 24415-66-5.

Reference:
Patent; Zhengzhou University; Liu Hongmin; Yu Bin; Yuan Shuo; Wang Shuai; Li Zhonghua; (21 pag.)CN109180684; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 1337532-51-0 , The common heterocyclic compound, 1337532-51-0, name is 5-Bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine, molecular formula is C7H7BrN4, 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 solution of 1-(4-bromo-3-fluorophenyl)-3-(2,5-difluorophenyl)pyrrolidin-2-one (0.3 g, 0.8 mmol, 1.0 equiv ) in 1 ,4-dioxane (20 mL) was added bis(pinacolato)diboron (0.24 g, 1.0 mmol, 1.2 equiv) and potassium carbonate (0.33 g, 2.4 mmol, 3.0 equiv). The reaction mixture was degassed with N2 for 15 minutes, PdCl2(dppf)-CH2Cl2 adduct (0.033 g, 0.04 mmol, 0.05 equiv) was added and the reaction mixture was stirred for 3 hours at 100 C in a sealed tube. The reaction was cooled to room temperature, 5-bromo-7- methyl-7/-/-pyrrolo[2,3-c]pyrimidin-4-amine (0.27 g, 1.2 mmol, 1.5 equiv) and saturated aqueous NaHC03 (10 mL) were added, and N2 gas was bubbled through the mixture for 10 minutes. PdCl2(dppf)-CH2Cl2 adduct (0.033 g, 0.040 mmol, 0.05 equiv) was added, the vessel was sealed, and the reaction mixture was stirred at 100 C for 16 h. The reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate (2 x 20 mL). The organics were combined and dried over Na2S04, filtered, and concentrated in vacuo to get crude compound. Crude product was purified by flash chromatography on silica gel and compound was eluted with 3% MeOH/DCM. The fractions containing the desired product were combined and concentrated to afford 1-4-(4-amino-7-methyl-7/-/-pyrrolo[2,3- d]pyrimidin-5-yl)-3-fluorophenyl)-3-(2,5-difluorophenyl)pyrrolidin-2-one (20 mg, 5.6 %) as off white solid. LCMS (ES) m/z = 438.3 [M+H]+. H NMR (400 MHz, DMSOd6) delta ppm 2.21 – 2.31 (m, 2 H), 3.74 (s, 3 H), 3.97 (t, J=7.6 Hz, 2 H), 4.20 – 4.30 (m, 1 H), 5.98 (br s,2 H), 7.18 – 7.22 (m, 1 H), 7.27 – 7.31 (m, 3 H), 7.39 – 7.45 (m, 1 H), 7.59 (d, J=8.4 Hz, 1 H), 7.81 (d, J=11.6 Hz, 1 H), 8.14 (s, 1 H).

The synthetic route of 1337532-51-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AXTEN, Jeffrey M.; MEDINA, Jesus Raul; WO2015/136463; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products 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.

Step (i): Synthesis of (S)-2-(2-chloro-6-phenyl-pyrimidin-4-ylamino)-2-phenyl-ethanol To 2,4-dichloro-6-phenylpyrimidine (642 mg, 2.8 mmol), dissolved in 30 mL methanol, was added DIEA (0.41 mL, 3 mmol) and was stirred for 25 min at about 20-35 C. under a nitrogen atmosphere. To this mixture was added (S)-(+)-2-phenyl glycinol (411 mg, 3 mmol) and stirred for 22 h. An additional DIEA (0.41 mL, 3 mmol) was added, and the mixture was stirred for about 10-19 h. The mixture after concentrating by rotary evaporation and purification (Biotage Horizon HPFC system chromatography, SiO2, 35:65 EtOAc:hexane) gave the title compound as a white solid (367 mg, 39% yield).1H NMR (300 MHz, DMSO-d6): delta 8.43 (apt d, J=7.8 Hz, 1H), 7.92 (b s, 2H), 7.50-7.22 (m, 8H), 7.08 (s, 1H), 5.18 (b s, 1H), 5.03 (b s, 1H), 3.68 (b s, 2H).LC-MSD (ES+): m/z [326 (M+H)+, 100].

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; Dr. Reddy’s Laboratories Ltd.; US2010/144722; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 126728-20-9 ,Some common heterocyclic compound, 126728-20-9, molecular formula is C7H3Cl2N3, 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.

2,4-Dichloropyrido[2,3-d]pyrimidine (170.0 mg, 0.85 mmol) and 2-(4-nitrophenyl)ethan-1-amine hydrochloride (172.0 mg, 0.85 mmol) were dissolved in iPrOH (8.5 mL), and Et3N (250.0 muL, 1.80 mmol) was added thereto at room temperature. The reaction mixture was stirred at 21C for 5 hours and distilled under reduced pressure. After addition of CH2Cl2and water, the residue was stirred. The obtained solid was filtered and dried to obtain the white solid compound, 2-chloro-N-(4-nitrophenethyl)pyrido[2,3-d]pyrimidin-4-amine (250.0 mg, 89%).[735][736]1H NMR (300 MHz, DMSO-d6) delta = 9.15 (t,J= 5.3 Hz, 1H), 8.97 (d,J= 2.7 Hz, 1H), 8.71 – 8.61 (m, 1H), 8.20 – 8.12 (m, 2H), 7.62 – 7.52 (m, 3H), 3.86 – 3.74 (m, 2H), 3.17 – 3.06 (m, 2H)[737]LC/MS ESI (+): 330 (M+1)

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. 126728-20-9, 2,4-Dichloropyrido[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; C&C RESEARCH LABORATORIES; PARK, Chan Hee; IM, Jun Hwan; LEE, Soon Ok; LEE, Sang Hwi; KO, Kwang Seok; KIM, Byung Ho; MOON, Hyung Jo; KIM, Jae Ill; PARK, Heon Kyu; HONG, Yeon Ju; (0 pag.)WO2019/231271; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 75833-38-4 , The common heterocyclic compound, 75833-38-4, name is 2-Chloropyrimidine-4-carbonitrile, molecular formula is C5H2ClN3, 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.

a) 2-Chloropyrimidine-4-carboxamide 338 g of 98% strength formic acid are introduced into a 1–1 round bottom flask fitted with magnetic stirring and containing 131.9 g (946 mmol) of 2-chloropyrimidine-4-carbonitrile, and a stream of gaseous hydrochloric acid is passed through slowly for 1 h 30 min. The mixture is allowed to stand overnight, the solid is isolated on sintered glass and is then purified by recrystallisation with filtration while hot, from a mixture of nitromethane and ethyl acetate. In this way, 107.03 g of grey solid are isolated as three crops, after drying under vacuum and with heating. Melting point: 152.5-154 C.

The synthetic route of 75833-38-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Synthelabo; US5164397; (1992); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 74-69-1, 2-Methyl-4-pyrimidinamine, 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-Methyl-4-pyrimidinamine, blongs to pyrimidines compound. Application In Synthesis of 2-Methyl-4-pyrimidinamine

Example 1; 3-Chloro-2-methyl-N-(2-methyl-pyrimidin-4-yl)-benzenesulfonamide; 2-Methyl-pyrimidin-4-ylamine (91 mg, Gabriel, Chem. Ber. 37, 1904, 3641) and 3-chloro-2-methyl-benzenesulfonyl chloride (179 mg) were dissolved in pyridine (5 mL) and the resulting mixture was allowed to stir at 50 to 60 C. for 48 hours. The mixture was then evaporated in vacuo and the residue was dissolved in ethyl acetate. The solution was washed with 1M CuSO4 solution twice, dried over Na2SO4, filterd and evaporated. The residue was purified by flash chromatography (CH2Cl2MeOH/NH3 90:10:0.5) to give the desired product 3-chloro-2-methyl-N-(2-methyl-pyrimidin-4-yl)-benzenesulfonamide as a yellow powder (22 mg). MS (ESI-): 297.1 ([M-H]-).

The synthetic route of 74-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Amrien, Kurt; Hunziker, Daniel; Kuhn, Bernd; Mayweg, Alexander; Neidhart, Werner; US2005/288308; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 219599-99-2, Adding some certain compound to certain chemical reactions, such as: 219599-99-2, name is 2-(tert-Butyl)-4-(piperazin-1-yl)-6-(trifluoromethyl)pyrimidine,molecular formula is C13H19F3N4, 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 219599-99-2.

b) 1-(4-{4-[2-tert-Butyl-6-(trifluoromethyl)pyrimidin-4-yl]piperazin-1-yl}butyl)-3,4-dihydro-1H-1-benzazepine-2,5-dione 1-(4-Chlorobutyl)-3,4-dihydro-1H-1-benzazepine-2,5-dione (3.29 mmol, 1.75 g, 70%), 2-tert-butyl-4-piperazin-1-yl-6-(trifluoromethyl)pyrimidine (3.56 mmol, 1.03 g; preparation according to WO 99/02503) and triethylamine (13.17 mmol, 1.33 g) in dimethylformamide (100 ml) were stirred at 100 C. for 12 h. Afterward, ethyl acetate was added and the mixture was washed twice with water. The combined organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure. The oily residue was purified by chromatography on silica gel (eluent: 95:5 v/v dichloromethane:methanol); yield 0.42 g. ESI-MS: 519.2, [M+H+]=518.2, 259.6; 1H NMR (500 MHz, CDCl3) delta (ppm): 7.57-7.52 (2H, m), 7.29 (1H, t), 7.25 (1H, d+CHCl3), 6.57 (1H, s), 3.92 (2H, s br.), 3.63 (4H, s br.), 3.01-2.95 (2H, m), 2.80 (2H, t), 2.41 (4H, t), 2.28 (2H, t), 1.53 (2H, quint.), 1.42 (2H, quint.), 1.34 (9H, s).

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. 219599-99-2, 2-(tert-Butyl)-4-(piperazin-1-yl)-6-(trifluoromethyl)pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Lubisch, Wilfried; Haupt, Andreas; US2007/219182; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 4270-27-3 , The common heterocyclic compound, 4270-27-3, name is 6-Chloropyrimidine-2,4(1H,3H)-dione, molecular formula is C4H3ClN2O2, 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.

[Example 31] Preparation of 1-(4-chlorobenzyl)-3-(2-methoxycarbonyl-2-methylpropyl)-6-(6-trifluoromethyl-2-pyridylamino)pyrimidine-2,4(1H, 3H)-dion (I-108) To a mixture of 6-chlorouracil (5.00 g, 34.1 mmol) and DMF (100 mL) were added 60% sodium hydride (1.64 g, 40.9 mmol) and lithium bromide (2.96 g, 34.18 mmol), and the resulting mixture was stirred at room temperature for 1 hour. To the reaction mixture was added 4-chlorobenzylbromide (7.71 g, 37.5 mmol), and the resulting mixture was stirred for additional 21 hours. To the reaction mixture was added water (100 mL), and the precipitated solid was filtered off. The solid was purified by silica gel column chromatography (ethyl acetate/hexane) and precipitated by methanol/ethyl acetate/hexane to give 6-chloro-1-(4-chlorobenzyl)pyrimidine-2,4(1H, 3H)-dion (3.87 g, Yield: 42%) as colorless solid. 1H-NMR (delta ppm TMS/DMSO-d6): 5.14 (2H, s), 5.96 (1H, s), 7.31 (2H, d, J=8.0 Hz), 7.43 (2H, d, J=8.0 Hz), 11.76 (1H, s).

The synthetic route of 4270-27-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi & Co., Ltd.; KAI, Hiroyuki; ENDOH, Takeshi; JIKIHARA, Sae; ASAHI, Kentaro; HORIGUCHI, Tohru; EP2604260; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia