Day: July 27, 2021

Electric Literature of 22536-66-9, 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. 22536-66-9, name is 2-Chloropyrimidine-4-carboxamide, molecular formula is C5H4ClN3O, 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.

Example 591 2-(2-{[2-amino-6-(3-chloro-2-methylphenyl)pyrimidin-4- yl]amino}ethoxy)pyrimidine-4-carboxamide A mixture of 2-[[2-amino-6-(3-chloro-2-methyl-phenyl)pyrimidin-4- yl]amino]ethanol, 2-chloropyrimidine-4-carboxamide (1.5 equiv.) and CS2CO3 (2.0 equiv.) in DMSO was heated in a sealed tube at 90 C for 16 h. After cooling was methanol added to the solution followed by filtration and purification by preparative HPLC to give the title compound. LCMS [M+H]+ 400. 1 H NMR (400 MHz, METHANOL-^) delta ppm 8.78 (d, J=5.1 Hz, 1 H), 7.68 (d, J=5.1 Hz, 1 H), 7.40 (dd, J=7.4, 1.7 Hz, 1 H), 7.16 – 7.24 (m, 2 H), 5.82 (br. s., 1 H), 4.67 (t, J=5.5 Hz, 2 H), 3.73 – 3.92 (m, 2 H), 2.31 (s, 3 H).

According to the analysis of related databases, 22536-66-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THOMAS HELLEDAYS STIFTELSE FOeR MEDICINSK FORSKNING; SCOBIE, Martin; WALLNER, Olov; KOOLMEISTER, Tobias; VALLIN, Karl Sven Axel; HENRIKSSON, Carl Martin; HOMAN, Evert; HELLEDAY, Thomas; JACQUES, Sylvain; DESROSES, Matthieu; JACQUES-CORDONNIER, Marie-Caroline; FISKESUND, Roland Julius Yu; (359 pag.)WO2015/187089; (2015); 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. 5177-27-5, name is 5-Amino-2,4-dichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 5-Amino-2,4-dichloropyrimidine

To a round-bottomed flask equipped with a magnetic stirrer was added 2,4-dichloropyrimidin-5-amine B (1.89 g, 11.52 mmol), DIPEA (8.05 mL, 46.1 mmol), morpholine-3-carboxylic acid A (1.66 g, 12.68 mmol), and DMSO (5 mL). The reaction was stirred at 100oC overnight. The mixture was poured into water and extracted with EtOAc for three times. The pH of the aqueous layer was adjusted (about 5) with 10 percent citric acid and extracted again with EtOAc. The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo to furnish a tan solid. The solid was triturated in diethyl ether containing a small amount of EtOH, filtered, and dried to give 2-chloro-6a,7,9,10-tetrahydro -[1,4]oxazino[3,4-h]pteridin -6(5H)-one C: 1.95 g (70.3% yield). MS [M+H] found 241.

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, 5177-27-5, 5-Amino-2,4-dichloropyrimidine.

Reference:
Article; Jin, Stanley; Mikami, Satoshi; Scorah, Nick; Chen, Young; Halkowycz, Petro; Shi, Lihong; Kahana, Jason; Vincent, Patrick; de Jong, Ron; Atienza, Joy; Fabrey, Robyn; Zhang, Lilly; Lardy, Matthew; Bioorganic and Medicinal Chemistry Letters; vol. 29; 21; (2019);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 3977-48-8, 4,6-Diphenylpyrimidine, 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, SDS of cas: 3977-48-8, blongs to pyrimidines compound. SDS of cas: 3977-48-8

Step 2: Synthesis of di-mu-chloro-bis[bis(4,6-diphenylpyrimidinato)iridium(III)] (abbreviation: [Ir(dppm)2Cl]2) Next, into a recovery flask equipped with a reflux pipe, 15 mL of 2-ethoxyethanol, 5 mL of water, 1.10 g of Hdppm obtained in the above Step 1, and 0.69 g of iridium chloride hydrate (IrCl3.H2O) were put, and the air in the flask was replaced with argon. After that, irradiation with microwaves (2.45 GHz, 100 W) was performed for one hour. After the solvent was distilled off, the obtained residue was washed with ethanol to give a dinuclear complex [Ir(dppm)2Cl]2 (reddish brown powder, yield of 88%). A synthesis scheme (a-2) of Step 2 is shown below.

The synthetic route of 3977-48-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SEMICONDUCTOR ENERGY LABORATORY CO., LTD.; Kitano, Yasushi; Osaka, Harue; Shitagaki, Satoko; US2013/48971; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 3764-01-0, 2,4,6-Trichloropyrimidine, 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, Formula: C4HCl3N2, blongs to pyrimidines compound. Formula: C4HCl3N2

To an ice-cold solution containing 2, 4, 6-trichloropyrimidine (8 g, 44 mmol) in MeOH (80 mL) and NAHCO3 (10 g) add slowly and dropwise a methanolic solution (20 mL) of morpholine (4 mL, 46 mmol). Allow the mixture to warm to 25C and stir overnight. Before diluting with water, vigorously stir for 1 hour, and filter to give white crystalline solid (10 g) as a mixture of regioisomers. Carefully recrystallize from toluene to give 6-morpholino-2, 4- dichloropyrimidine. Concentrate the mother liquor and carefully recrystallize from ETOH to give 4, 6-dichloro-2-morpholinopyrimidine.

The synthetic route of 3764-01-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEUROGEN CORPORATION; WO2005/7648; (2005); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1546-78-7, 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 1546-78-7 as follows.

Take 0.17g (0.001mol) 4- hydroxy-6-trifluoromethyl-pyrimidine (prepared as described in Example 1), 0.23g (0.001mol) 4- chloro-1- (4-chlorophenyl) -1H – pyrazole (prepared as in Example 2), 0.14g (0.001mol) of potassium carbonate in 50ml single neck flask, 10mlN, N- dimethylformamide as a solvent, was heated to 100 deg.] C, the reaction 4-10 hours, TLC after completion of the reaction was monitored, the solvent was distilled off under reduced pressure, was added (3 × 50ml) and extracted with ethyl acetate, the organic phase was washed with saturated brine 50ml, after solvent removal the residue by column chromatography (eluent, ethyl acetate and petroleum ether , a volume ratio of 1: 2) to obtain 0.26 g of a white solid, yield 72.5%,

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1546-78-7, its application will become more common.

Reference:
Patent; Shenyang Sinochem Agrochemicals R&D Co., Ltd.; Sun, Xufeng; Guan, Aiying; Zhao, Jie; Ma, Sen; Sun, Qin; Chen, Xuanming; Liu, Zhangling; (40 pag.)CN105777717; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1683-75-6, 2-Amino-4-chloro-5-fluoropyrimidine, 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: C4H3ClFN3, blongs to pyrimidines compound. HPLC of Formula: C4H3ClFN3

General procedure: To a mixture of (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl)-1H-benzo[d]imidazole derivatives (7 mmol, 1 eq.), which was commercially available or prepared according to the literature procedure [WO2016192630], amino aromatic chloride (1.1 eq.) in DMF (20 mL) was added Na2CO3 aq. (3 eq.). The mixture was bubbled with Ar for 15 mins and then Pd(dppf)Cl2 (0.1 eq.) was added. The mixture was heated to 80oC and stirred for 4-6 hours under Ar atmosphere, then cooled to room temperature and concentrated to remove the organic solvent after reaction completion. The residue was diluted with water (100 mL) and extracted with EA (150 mL×3). The organic layer was separated and washed with saturated brine, then dried with anhydrous Na2SO4. The organic phase was then concentrated and the residue was further purified with flash chromatography or preparative HPLC to afford the desired intermediate compounds 3a-3j, which were characterized by LC-MS.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1683-75-6, 2-Amino-4-chloro-5-fluoropyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Zha, Chuantao; Deng, Wenjia; Fu, Yan; Tang, Shuai; Lan, Xiaojing; Ye, Yan; Su, Yi; Jiang, Lei; Chen, Yi; Huang, Ying; Ding, Jian; Geng, Meiyu; Huang, Min; Wan, Huixin; European Journal of Medicinal Chemistry; vol. 148; (2018); p. 140 – 153;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 50270-27-4, 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.50270-27-4, name is 2,4,6-Trichloropyrimidine-5-carbaldehyde, molecular formula is C5HCl3N2O, molecular weight is 211.4332, as common compound, the synthetic route is as follows.

N-{4-[1-(1-benzylpiperidin-4-yl)-4-(3,6-dihydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]phenyl}acetamide (Scheme 6)Example 3To a solution of 2,4,6-trichloro-pyrimidine-5-carbaldehyde (1.53 g, 7.19 mmol) in anhydrous ethanol (25 mL) at -78° C. was added (1-benzyl-piperidin-4-yl)-hydrazine hydrochloride (2 g, 7.19 mmol) and triethylamine (5.01 mL). After 30 min allow the reaction mixture to warm to 0° C. After 1 h warm to 25° C. Add ethyl acetate and extract with saturated aqueous sodium bicarbonate, water (2.x.) and brine. Dry over anhydrous magnesium sulfate. Concentrate in vacuo to give an oil. Add diethyl ether and remove precipitate by filtration. Concentrate mother liquor and add diethyl ether and remove precipitate by filtration. Add 2N HCl in diethyl ether to mother liquor and collect the precipitate. 1-(1-Benzyl-piperidin-4-yl)-4,6-dichloro-1H-pyrazolo[3,4-d]pyrimidine hydrochloride is obtained as a white solid is obtained. A mixture of this white solid (530 mg, 1.34 mmol), tributyl-(3,6-dihydro-2H-pyran-4-yl)-stannane (500 mg), PdCl2(PPh3)2 (50 mg), diisopropylethyl amine (230 muL) in dimethylformamide (6 mL) is heated to 70° C. After 3 h at 70° C. and 18 h at 60° C.° the dimethylformamide is removed in vacuo. The residue is dissolved in dichloromethane and washed with saturated aqueous sodium bicarbonate. The organic phase is dried over anhydrous magnesium sulfate and concentrated in vacuo to give a dark oil. The oil is treated with 4-acetamidophenylboronic acid (72 mg, 0.402 mmol), Pd(PPh3)4 (5 mg) and 2M aqueous sodium carbonate (0.281 mL, 0.563 mmol) in dimethoxyethane (1 mL) and heated in a microwave at 175° C. for 15 min. The reaction mixture is purified by reverse phase HPLC (CH3CN/H2O/CF3CO2H) followed by silica gel chromatography (CH2Cl2/MeOH) to give the title compound as a trifluoroacetate salt (7.7 mg).

The chemical industry reduces the impact on the environment during synthesis 50270-27-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Wyeth; US2009/192176; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 2434-56-2, Adding some certain compound to certain chemical reactions, such as: 2434-56-2, name is 4,6-Diaminopyrimidine,molecular formula is C4H6N4, 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 2434-56-2.

Compound 2~(5-chloro-2,4-dimethoxypheny])imidazo[l ,2-c]pyrimidin-7-amme 195 was prepared in the same manner as 2-(5-chloro-2,4-dimethox phenyl)-7-(pyrrolidin-l – yl)-imidazo[l ,2-o]pyridine 5a. Solid was basified with aqueous ammonia, washed with water, collected by filtration and dried. The product was obtained as a white solid (52 mg, 18% yield). 1H NMR (300 MHz, DMSO-d6): delta 8.96 (s, III), 8.14 (s, 1H), 7,99 (s, 1 H), 6.87 (s, 1H), 6.15 (tn, 2H), 4.01 (s, 3H), 3.94 (s, 3H); HPLC (Method 3) 95.12% (AUC), = 16.24 niin; ESI MS m/z 305 [M+H|+. A solution of 2-bromo-1-(5-chloro-2,4-dimethoxyphenyl)ethanone 3 (70 mg, 0.24 mmol) and 4-(pyrrolidin-1-yl)pyridin-2-amine 4a (39 mg, 0.24 mmol) in acetone (3 mL) was heated at 75 C for 16 h. The reaction mixture was cooled to room temperature; the white precipitate was collected by filtration, washed with acetone, and dried under reduced pressure to afford 2-(5-chloro-2,4-dimethoxyphenyl)-7-(pyrrolidin-1-yl)imidazo[1 ,2-a]pyridine hydrobromide 5a (45 mg, 43%) as a pink solid. 1H NMR (300 MHz, DMSO-d6) . delta 13.03 (s, 1H), 8.50 (d, J = 7.6 Hz, 1H). 8.20 (s, 1H), 7.89 (s, 1H), 6.97 (s, 1H), 6.95 (dd, J=2.2, 7.6 Hz, 1H), 6.30 (d, J= 2.0 Hz, 1H), 4.05 (s, 3H), 3.99 (s, 3H). 3.48-3.38 (m, 4H), 2.08- 1.98 (m, 4H); HPLC ( Method 4) 98.7% (AUG), tR = 19.02 min. APCI MS m/z 358 [M + H]+ .

According to the analysis of related databases, 2434-56-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ONCOTHERAPY SCIENCE, INC.; MATSUO, Yo; HISADA, Shoji; NAKAMURA, Yusuke; CHAKRABARTI, Anjan; RAWAT, Manish; RAI, Sanjay; SATYANARAYANA, Arvapalli, Venkata; DUAN, Zhiyong; TALUKDAR, Arindam; RAVULA, Srinivas; DECORNEZ, Helene; (491 pag.)WO2017/58503; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 42754-96-1 , The common heterocyclic compound, 42754-96-1, name is 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C5H2Cl2N4, 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 4,6-dichloro-1H-pyrazolo [3,4-d] pyrimidine 1a (120 mg, 0.63 mmol),4-methoxybenzylamine 1b (87.1 mg, 0.63 mmol)And triethylamine (64.13 mg, 0.63 mmol) were dissolved in 2 mL of a tetrahydrofuran solution and stirred at room temperature for 1 hour.The reaction was stopped and distilled under reduced pressure. The residue was purified by silica gel column chromatography using eluent system A,The title product 1c (140 mg) was obtained in a yield of 76.1%.

The synthetic route of 42754-96-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Hengrui Pharmaceutical Co., Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; Yang Shibo; You Lingfeng; Feng Jun; He Feng; (49 pag.)CN110526918; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 69034-12-4, 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.69034-12-4, name is 2-Chloro-5-(trifluoromethyl)pyrimidine, molecular formula is C5H2ClF3N2, molecular weight is 182.531, as common compound, the synthetic route is as follows.

To a stirred solution of methyl-2-(2-fluorophenyl)-2-(4-(4,4,5,5-tetramethyl- l ,3,2-dioxaborolan-2-yl)phenyl)acetate (1.83 g, 4.8 mmol) in dioxane (80 mL) and water (20 mL) was added 2-chloro-5-trifluoromethylpyrimidine (1.0 g, 5.5 mmol) and K2C03 (1.35 g, 9.8 mmol). The mixture was degassed with N2 for 5 min, treated with Pd(PPh3)4 (280 mg, 0.24 mmol) and heated at 110 C overnight (LCMS indicated completion of the reaction). The mixture was cooled to r.t., treated with water (100 mL) and extracted with DCM (2 x 100 mL). The combined organic phase was separated, dried (MgS0 ), and evaporated in vacuo. Purification by chromatography (Si02) eluting with isohexane/ethyl acetate (95:5) afforded the subtitle compound as a white solid (1.45 g, 74% yield). LCMS (Rt 3.54 min, [M+H]+ 391). N.M.R. (CDC13) 9.01 (s, 2H), 8.48 (d, 2H, J = 8.4 Hz), 7.47 (d, 2H, J = 8.4 Hz), 7.30-7.25 (m, 2H), 7.13-7.05 (m, 2H), 5.38 (s, 1H), 3.78 (s, 3H).

Statistics shows that 69034-12-4 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-(trifluoromethyl)pyrimidine.

Reference:
Patent; CHDI FOUNDATION, INC.; DOMINGUEZ, Celia; MUNOZ-SANJUAN, Ignacio; BEAUMONT, Vahri; BECONI, Maria; BUeRLI, Roland, W.; HAUGHAN, Alan, F.; LUCKHURST, Christopher, A.; WALL, Michael; RAPHY, Gilles; THOMAS, Beth; WO2014/159210; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia