Month: May 2021

Electric Literature of 22536-61-4, 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 22536-61-4, name is 2-Chloro-5-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

[0409j (E)-5-methyl-2-(prop-1-en-1-yl)pyrimidine, Example 14.01. To a 500 mL round bottomed flask was added 2-chloro-5-methylpyrimidine (12 g, 93 mmol), potassium (E)-trifluoro(prop-1-en-1-yl)borate (17.27 g, 117 mmol), and potassium phosphate (59.4 g, 280 mmol). The flask was purged with N2 (5x) and then 1,4-dioxane (200 mL) and water (20 mL) were added. The resulting yellow suspension was bubbled with Ar for 15 mm and then 1,1 -bis [(di-t-butyl-p-methylaminophenyljpalladium(II) chloride (Amphos, commercially avaliable from Strem, 2.64 g, 3.73 mmol) was added, a reflux condenser was attached and the reaction warmed to 90 C in an oil bath and stirred under N2 for 16.5 h. The reaction was then cooled to RT. The reaction was diluted with water (250 mL), and extracted with EtOAc (2 x 250 mL). The organic layers were combined, dried (MgSO4), and concentrated. The residue was purified by flash chromatography on silica gel eluting with 0-20% EtOAc/hexanes) to afford (E)-5-methyl- 2-(prop-1-en-1-yl)pyrimidine 14.01 (12.96 g, 97 mmol, 100% yield) as a yellow/orange oily solid. ?H NMR (300 MHz, CDC13) = 8.49 (s, 2H), 7.0 1-7.20 (m, 1H), 6.57 (dd, J= 15.6, 1.7 Hz, 1H), 2.29 (s, 3H), 1.97 (dd, J= 6.8, 1.6 Hz, 3H). MS (ESI pos. ion) m/z:(M–H).

According to the analysis of related databases, 22536-61-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HEATH, Julie Anne; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KHAKOO, Aarif Yusuf; KOPECKY, David John; LAI, Su-Jen; MA, Zhihua; MCGEE, Lawrence R.; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; YANG, Kevin; YEH, Wen-Chen; DEBENEDETTO, Mikkel V.; FARRELL, Robert P.; HEDLEY, Simon J.; JUDD, Ted C.; KAYSER, Frank; (1266 pag.)WO2016/187308; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 35265-82-8, 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 35265-82-8, name is 2,4-Dichloro-6-methylthieno[3,2-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 2,4-dichloro-6-methylthieno[3,2-d]pyrimidine (450 mg, 2.05 mmol), aqueous NaOH (1N, 4 mL) and THF (4 mL) was stirred at room temperature under N2. The reaction was monitored by HPLC until the reaction was completed. Then the mixture was neutralized to PH 5 by addition of 2N aqueous HCl. The solid was filtrated and dried to give 380 mg of 2-chloro-6-methylthieno[3,2-d]pyrimidin-4(3H)-one (yield was 92%) as a yellow solid. MS obsd. (ESI+) [(M+H)+]: 201.

According to the analysis of related databases, 35265-82-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc; Liang, Chungen; Wang, Lisha; Yun, Hongying; Zheng, Xiufang; US2013/90328; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 90905-32-1, 2-Methoxypyrimidine-5-carbaldehyde, 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, Product Details of 90905-32-1, blongs to pyrimidines compound. Product Details of 90905-32-1

To a stirred solution of 4-bromothiazole (50.0 mg, 0.3 05 mmol) in THF (2 mL) under nitrogen atmosphere was added n-butyllithium (2.5 molar solution in hexane) (0.183 mL, 0.45 7 mmol) at – 78 C. Resulting pale yellow solution was stirred at -78 C for 30 mm. Then, 2- methoxypyrimidine-5-carbaldehyde (37.9 mg, 0.274 mmol) in 0.5 mL THF was added and the reaction mixture was stirred at -78 C for 1 h. Reaction was quenched with water (2 mL) anddiluted with ethyl acetate (5 mL). The organic layer was separated, washed with brine, dried over anhydrous sodium sulphate and evaporated under vacuum to get the crude product. The crude product was purified by combiflash chromatography (4 g Redisep Si02 column, eluting with 72% EtOAc in n-hexanes) to afford the title compound 143A (30 mg, 32%) as a pale yellow oil. LC-MS retention time = 0.84 mm; m/z = 304.0 [M+Hf AQUITY UPLC BEH C18 (3.0 x 50mm)1.7 micron column; Mobile Phase A: 5 mM ammonium acetate in 95% Water/ 5% ACN; Mobile Phase B: 5 mM ammonium acetate in 5% Water/ 95% ACN; Gradient time 1.7 mm. 20% B to 90% B over 1.7 mm. Flow rate 0.7 mL/min; Detection: UV at 220 nm. 1H NMR (400 MHz, CD3OD) oe ppm 8.63 (s, 2H), 7.55 (s, 1H), 6.05 (s, 1H), 4.03 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90905-32-1, 2-Methoxypyrimidine-5-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHAO, Guohua; DEVASTHALE, Pratik; YE, Xiang-Yang; SELVAKUMAR, Kumaravel; DHANUSU, Suresh; BALASUBRAMANIAN, Palanikumar; GUERNON, Leatte R.; CIVIELLO, Rita; HAN, Xiaojun; PARKER, Michael F.; JACUTIN-PORTE, Swanee E.; (290 pag.)WO2018/89353; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 425394-89-4 , The common heterocyclic compound, 425394-89-4, name is 4,6-Dichloropyrimidin-5-ol, molecular formula is C4H2Cl2N2O, 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 No.31 4-(hydroxymethyl)cyclohexan-1-ol (0.237 g, 1.82 mmol) in No.13 THF (15 mL) was added No.23 triphenylphosphine (0.718 g, 2.74 mmol) and No.23 4,6-Dichloropyrimidin-5-ol (0.3 g, 1.82 mmol). To the mixture was added No.31 di-tert-butyl azodicarboxylate (0.63 g, 2.74 mmol) at 0C., the mixture was stirred at room temperature for 18 hr. The reaction mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=9:1 as eluent) to afford the 4-(((4,6-dichloropyrimidin-5-yl)oxy)methyl)cyclohexan-1-ol (0.15 g, 30% yield). LC/MS APCI: Calculated 276.04; Observed m/z [M+H)]+ 277.0.

The synthetic route of 425394-89-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Arrien Pharmaceuticals LLC; Vankayalapati, Hariprasad; US2020/131154; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 13036-57-2, 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. 13036-57-2, name is 2-Chloro-4-methylpyrimidine, molecular formula is C5H5ClN2, 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.

To a solution of 2-chloro-4-methylpyrimidine (Ig5 7.78mmol) and zinc cyanide (475mg, 4.04mmo) in anhydrous DMF (10ml) was added Pd(PPh3)4 (449mg, 0.366mmol) and nitrogen flushed through the mixture for 5 min. The mixture was heated at 180C for 30 min in a microwave reactor. The reaction was repeated on the same scale and the reaction mixtures were combined. The mixture was partitioned between EtOAc and water (filtered through celite to remove some insolubles), and the organic layer washed with sat. NaCl5 dried over MgStheta4, filtered and evaporated. The residue was purified by MPLC (Biotage Horizon; FLASH 25+M) eluent: 100% Hexanes (90ml), gradient rising from 100% Hexanes to 15% EtOAc in Hexanes (900ml), then 15% EtOAc in Hexanes (500ml) to give Ig of the title compound (54%) as an off- white solid. 1H NMR (CDCl3): 2.62 (s, 3H), 7.42 (d, J 5.1 Hz, 1H)5 8.69 (d, J 5.1 Hz, 1H).

According to the analysis of related databases, 13036-57-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; EDMONDSON, Scott, D.; CHANG, Lehua; KAR, Nam Fung; MORRIELLO, Gregori, J.; MOYES, Christopher, J.; SHEN, Dong-Ming; ZHU, Cheng; ANTHONY, Neville, J.; JONES, Philip; SMITH, Graham, F.; SCOTT, Mark, E.; THOMPSON, Christopher, F.; JUNG, Joon; CAMMARANO, Carolyn; HOFFMAN, Dawn Marie; WO2011/25774; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 55583-59-0, 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 55583-59-0, name is 2,5-Diamino-4,6-dichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 2 Preparation of N-(2-amino-4,6-dichloropyrimidin-5-yl)-formamide 2,5-Diamino-4,6-dichloropyrimidine (0.01 mol; 2.0 g) and water (0.25 mol; 4.55 ml) were stirred at room temperature. 98% strength formic acid (0.4 mol; 18.27 g; 14.97 ml) was then added to the reaction. The reaction was subsequently heated to 50-55 C. and kept at this temperature for 3 h. Toluene (0.38 mol; 34.6 g; 40 ml) was then added for the azeotropic distillation under high vacuum at 50 C. (toluene was added twice to guarantee a good distillation, i.e. a total of 80 ml). The product was subsequently filtered, washed with water and then dried at 60 C. in vacuo. 0.01 mol (2.0 g) of the abovementioned product was obtained, corresponding to a yield of about 90%.

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 55583-59-0, 2,5-Diamino-4,6-dichloropyrimidine.

Reference:
Patent; Lonza AG; US6271376; (2001); B1;,
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. 3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine

To a stirred solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (5.0 g, 32.56 mmol, 1 equiv) in DMF (50 mL) was added 60% sodium hydride (1.5 g, 39.07 mmol, 1.2 equiv) at 000 and stirred for 15 mm followed by addition of (2-(chloromethoxy)ethyl)trimethylsilane(5.7 mL, 32.56 mmol, 1.0 equiv) at same temperature. The reaction mixture was warmed to room temperature and stirred for 1 h. The reaction mixture was quenched with ice water. The crude product was extracted in to ethyl acetate. The organic layer was dried over sodium sulphate and evaporated to obtain 4-chloro-7-((2-(trimethylsilyl) ethoxy) methyl)-7H-pyrrolo [2,3-d]pyrimidine as brown liquid (8.0 g, 66.0 %). LCMS (ES) m/z =284.10 [M+H]. 1H NMR (400 MHz, DMSO-d6) O ppm -0.11 (s, 9H), 0.79-0.81 (m, 2H),3.50 (t, J= 8.0 Hz, 2H), 5.62 (s, 1H), 6.68-6.69 (m, 1H), 7.85 (d, J=4.0 Hz, 1H), 8.62 (s, 1H).

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, 3680-69-1, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AXTEN, Jeffrey Michael; FAUCHER, Nicolas Eric; DAUGAN, Alain Claude-Marie; (110 pag.)WO2017/46738; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 332133-92-3, 4-(Tributylstannyl)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 4-(Tributylstannyl)pyrimidine, blongs to pyrimidines compound. Application In Synthesis of 4-(Tributylstannyl)pyrimidine

A mixture of 3 -(8-amino-S -bromo-2-(2-chloro-6-fluorobenzyl)-[1,2,4jtriazolo[1,5-ajpyrazin-6-yl)benzonitrile(51 mg, 0.11 mmol), CuT (4.2 mg,0.021 mmol), CsF (33 mg, 0.22 mmol), tetrakis(triphenylphosphine)palladium(0) (12mg, 0.012 mmol), and 4-(tributylstannyl)pyrimidine (49 mg, 0.13 mmol) in 1,4- dioxane (2 mL) was heated at 140 C for 1 h in a microwave reactor. The reaction mixture was concentrated under vacuum and the resulting residue was purified with flash chromatography to give the desired product as a light yellow oil. LC-MScalculated for C23H15C1FN8 (M+H): m/z = 457.1 found 457.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,332133-92-3, 4-(Tributylstannyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; INCYTE CORPORATION; HOANG, Gia; WANG, Xiaozhao; CARLSEN, Peter Niels; GAN, Pei; LI, Yong; QI, Chao; WU, Liangxing; YAO, Wenqing; YU, Zhiyong; ZHU, Wenyu; (333 pag.)WO2020/10197; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 355806-00-7, 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. 355806-00-7, name is (3R,5S,6E)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-[(methanesulfonyl) methylamino]pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoic acid tert-butyl ester, molecular formula is C26H36FN3O6S, 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 1; Hydrolysis of terf-butyl ester of rosuvastatin in aqueous solution of amines; 7.5 g of terf-butyl ester of rosuvastatin 38 ml of demineralized water 2 to 5 equivalents of amineThe reactants and water as the solvent are stirred in the autoclave from 98 to 1000C for 1 to 4 hours. The reaction mixture is sampled and analyzed by HPLC (“High Pressure Liquid Chromatography”) to find out the completion of reaction. Results are shown in Table 1. EPO

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 355806-00-7, (3R,5S,6E)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-[(methanesulfonyl) methylamino]pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoic acid tert-butyl ester.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; WO2006/136407; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 3435-25-4, 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 3435-25-4, name is 4-Chloro-6-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A solution of (S)isopropyl 2-(tert-butoxy)-2-(4-(8-fluorochroman-6-yl)-2,6-dimethyl-5 -(1,2,3,4- tetrahydroi soquinolin-6-yl)pyridin-3 -yl)acetate, 2 HC1 (0.015 g, 0.024 mmol), potassium carbonate (0.03 g, 0.217 mmol) and 4-chloro-6-methylpyrimidine (4.57 mg, 0.036 mmol) in dioxane (0.5 mL) was stirred at 100 C for 20 h in a sealed vial, and then treated withsodium hydroxide (0.02 g, 0.500 mmol) in EtOH (lml) at 85 C for 2 h. Then, cooled and purified by prep HPLC to afford (S)-2-(tert-butoxy)-2-(4-(8-fluorochroman-6-yl)-2,6- dimethyl-5-(2-(6-methylpyrimidin-4-yl)- 1,2,3 ,4-tetrahydroisoquinolin-6-yl)pyridin-3 – yl)acetic acid (0.0082 g, 0.013 mmol, 56.7% yield). LCMS (M+H) = 611.2.

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 3435-25-4, 4-Chloro-6-methylpyrimidine.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; KADOW, John F.; NAIDU, B. Narasimhulu; TU, Yong; (133 pag.)WO2017/29631; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia