Pyrimidines

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. 149849-94-5, name is Methyl 2-chloropyrimidine-4-carboxylate. A new synthetic method of this compound is introduced below., Recommanded Product: 149849-94-5

To a solution of 2-oxa-6-azaspiro[3.3]heptane hemioxalate (1.04 g) in dioxane (10 mL) was added triethylamine (1.55 mL) and the reaction mixture was stirred for 10 minutes at ambient temperature. Methyl 2-chloropyrimidine-4-carboxylate (500 mg) was added and the reaction mixture was stirred at 80 C for 6 hours in a Biotage Initiator microwave unit. To the reaction mixture was added water and the aqueous phase was extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude product was used without any further purification in the next step. MS (ESI) m/z 230.4 (M+H)+

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, 149849-94-5, Methyl 2-chloropyrimidine-4-carboxylate.

Reference:
Patent; ABBVIE INC.; ABBVIE DEUTSCHLAND GMBH & CO. KG; BRAJE, Wilfried; DOHERTY, George; JANTOS, Katja; JI, Cheng; JUDD, Andrew; KUNZER, Aaron; MASTRACCHIO, Anthony; SONG, Xiaohong; SOUERS, Andrew; SULLIVAN, Gerard; TAO, Zhi-Fu; LAI, Chunqui; KLING, Andreas; POHLKI, Frauke; TESKE, Jessc; WENDT, Michael; BRADY, Patrick; WANG, Xilu; PENNING, Thomas; MICHAELIDES, Michael; (448 pag.)WO2019/35927; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 14080-23-0, 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. 14080-23-0, name is 2-Cyanopyrimidine, molecular formula is C5H3N3, 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.

Step A: Preparation of methylpyrimidine-2-carboxylate: HCl gas was bubbled through methanol (“MeOH”, 700 mL) at a temperature of 0 C. for 30 minutes to give a saturated solution. Pyrimidine-2-carbonitrile (21.585 g, 205.38 mmol) was added to this solution, and the mixture was stirred at room temperature for 16 hours and then at a temperature ranging from about 40 to about 50 C. for 3 hours. The reaction mixture was concentrated, and the residue was dissolved in water. The pH was adjusted to about 7.0 using solid NaHCO3. The aqueous layer was extracted with 20% isopropyl alcohol (“iPrOH”)/dichloromethane (“DCM”) (3*). The combined organics were dried over sodium sulfate, filtered and concentrated under vacuum to give the desired product as white solids (23.0 g, 81%). 1H NMR (400 MHz, CDCl3) delta 8.97-8.96 (d, J=4.7 Hz, 2H), 7.53-7.50 (t, J=4.7 Hz, 1H), 4.09 (s, 3H).

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 14080-23-0, 2-Cyanopyrimidine.

Reference:
Patent; Array Biopharma, Inc.; US2010/63066; (2010); 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. 1202759-91-8, name is N4-(3-Aminophenyl)-5-fluoro-N2-(4-(2-methoxyethoxy)phenyl)pyrimidine-2,4-diamine. A new synthetic method of this compound is introduced below., Application In Synthesis of N4-(3-Aminophenyl)-5-fluoro-N2-(4-(2-methoxyethoxy)phenyl)pyrimidine-2,4-diamine

Weigh 24mg pentafluorobenzoic acid, 42mg HATU, 15mg HOAT in a 25ml round bottom flask and add 0.8mlDCM, 0.2 ml of DMF and 33 mul of DIEA as solvents were stirred at room temperature for about 10 minutes. 37 mg of the A1 intermediate was added to the reaction system. After stirring at room temperature for about 1 hour, 100 ml of saturated aqueous sodium bicarbonate solution was added, followed by 15 ml of DCM. The mixture was extracted 3 times and the resulting organic phase was dried under reduced pressure. The residue was applied to a silica gel column with DCM_MeOH=70:1 (v/v) to give 29 mg of the compound represented by Formula III-3 in 52% yield.

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, 1202759-91-8, N4-(3-Aminophenyl)-5-fluoro-N2-(4-(2-methoxyethoxy)phenyl)pyrimidine-2,4-diamine.

Reference:
Patent; Tsinghua University; Rao Yu; Liu Wanli; Yang Maojun; Sun Yonghui; (22 pag.)CN107973754; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 4595-59-9, Adding some certain compound to certain chemical reactions, such as: 4595-59-9, name is 5-Bromopyrimidine,molecular formula is C4H3BrN2, 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 4595-59-9.

Dissolve 5-bromopyrimidine (50.0 g, 314.4 mmol) in triethylamine (400 mL), add copper (1) iodide (1.20 g, 6.2 mmol) and stir mixture under nitrogen. After 15 minutes, add trimethylsilyl acetylene (53.3 mL, 377.3 mmol), followed by dichlorobis (triphenylphosphine) palladium (II) (8.82 g, 12.5 mmol) and stir at room temperature. After 3 hours, filter the solution through Celiteo, rinsing with ether. Concentrate the filtrate under reduced pressure. Purification by flash chromatography on silica gel eluting first with hexanes (100%), then with hexanes: ethyl acetate (3: 1) gives the title compound : lH NMR (CDC13) 8 9. 10 (s, 1H), 8.77 (s, 2H), 0.27 (s, 9H).

According to the analysis of related databases, 4595-59-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; WO2003/91226; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 148550-51-0, Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate, 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 Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate, blongs to pyrimidines compound. Application In Synthesis of Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate

To a solution of intermediate B (150mg, 0.76mmol) in MeCN (0.7ml) was added K2CO3. To this, a solution of intermediate A (174mg, 0.76mmol) in MeCN (0.7ml) was added dropwise resulting in a white suspension. Stirring at r.t. was continued for 30 EPO min after which the white suspension turned pale yellow. The reaction mixture was evaporated, re dissolved in EtOAc (10ml) and washed with water (5ml). The EtOAc layer was dried (Na2SO4) filtered and concentrated to dryness. Purification by flash chromatography (100percent DCM to 2percent MeOH/DCM) gave the title compound as an off- white solid (0.15g, 57percent). LCMS purity 89percent, m/z 349 [M+H]+.

The synthetic route of 148550-51-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHROMA THERAPEUTICS LTD; WO2006/123121; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 56844-12-3 , The common heterocyclic compound, 56844-12-3, name is 6-Bromo-4-chlorothieno[2,3-d]pyrimidine, molecular formula is C6H2BrClN2S, 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.

General procedure: 6-Bromo-4-chlorothieno[2,3-d]pyrimidine(5a) (200 mg, 0.802 mmol) was mixed with 1-phenylethanol (2a) (118 mg, 0.962 mmol), Cs2CO3( 313 mg, 0.962 mmol) and acetonitrile (2 mL). The reaction was then stirredunder nitrogen atmosphere at reflux and followed by GC. The mixture was cooledto rt, diluted with EtOAc (40 mL), washed with sat. aq. KHCO3 (20mL), water (2×20 mL) and brine (30 mL). The combined organic fractions weredried over Na2SO4 and concentrated in vacuum. Crudeproduct was absorbed onto Celite 545 and purified by silica gel columnchromatography (n-pentane/EtOAc,6/1). This gave 245 mg (0.730 mmol, 91%) of 6a as an off-white solid.

The synthetic route of 56844-12-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Han, Jin; Sundby, Eirik; Hoff, Bage H.; Journal of Fluorine Chemistry; vol. 153; (2013); p. 82 – 88;,
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 51421-99-9, name is 4-Chloro-2-methoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C5H5ClN2O

General procedure: This compound was prepared using a method analogousto that of Example 102 (intermediate 102.1 ), 4-chloro-2-methoxypyrimidine replacing 2,6-difluoropyridine andintermediate 132.4 replacing 2-chloro-5-hydroxybenzoicacid except that the reaction mixture was stirred for 30 min at80 C. LC-MS (B): tR=0.65 min; [M+H]+: 297.04

With the rapid development of chemical substances, we look forward to future research findings about 51421-99-9.

Reference:
Patent; Actelion Pharmaceuticals Ltd.; Hilpert, Kurt; Hubler, Francis; Murphy, Mark; Renneberg, Dorte; US2014/73651; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 3177-24-0, 2,4-Dichloropyrimidine-5-carbonitrile, 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, Recommanded Product: 3177-24-0, blongs to pyrimidines compound. Recommanded Product: 3177-24-0

General procedure: DIPEA (0.86mmol) was added to the solution of 2,4-dichloropyrimidine-5-carnonitrile (0.57mmol) in DMF (0.5ml) and stirred at room temperature for 10min. A solution of aminobenzene reagent corresponding to desired product (0.57mmol) in DMF (0.5ml) was added dropwise to the reaction mixture and stirred for 1h. The resultant was evaporated under vacuum and extracted with EtOAc. The organic layer was collected, washed with brine, dried over MgSO4, filtered, and dried under reduced pressure. 4c was obtained from the reaction of 4b, whereby substitution at the 2-position occurred.

The synthetic route of 3177-24-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Phuangsawai, Oraphan; Beswick, Paul; Ratanabunyong, Siriluk; Tabtimmai, Lueacha; Suphakun, Praphasri; Obounchoey, Phongphat; Srisook, Pimonwan; Horata, Natharinee; Chuckowree, Irina; Hannongbua, Supa; Ward, Simon E.; Choowongkomon, Kiattawee; Gleeson, M. Paul; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 896 – 905;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1195768-23-0, N-(3-(2-(tert-Butyl)-5-(2-chloropyrimidin-4-yl)thiazol-4-yl)-2-fluorophenyl)-2,6-difluorobenzenesulfonamide, 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, Recommanded Product: N-(3-(2-(tert-Butyl)-5-(2-chloropyrimidin-4-yl)thiazol-4-yl)-2-fluorophenyl)-2,6-difluorobenzenesulfonamide, blongs to pyrimidines compound. Recommanded Product: N-(3-(2-(tert-Butyl)-5-(2-chloropyrimidin-4-yl)thiazol-4-yl)-2-fluorophenyl)-2,6-difluorobenzenesulfonamide

Preparation Example 1 The preparation of the Known Crystal Form 1: Refer to the preparation method described in example 58a of patent document WO2009/137391A2 or U.S. Pat. No. 7,994,185B2, with the details as follows: Add N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide (196 mg, 0.364 mmol) and 7M methanol solution of ammonia (8 ml, 56 mmol) into a 25 mL autoclave, heat to 90 C. and react for 24 h; when the TLC shows the raw material is completely reacted, cool the above reaction system to room temperature, filter to get N-{3-[5-(2-amino-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide (i.e. Dabrafenib). 1H-NMR (400 MHz, DMSO-d6) delta ppm 10.83 (s, 1H), 7.93 (d, J=5.2 Hz, 1H), 7.55-7.70 (m, 1H), 7.35-7.43 (m, 1H), 7.31 (t, J=6.3 Hz, 1H), 7.14-7.27 (m, 3H), 6.70 (s, 2H), 5.79 (d, J=5.13 Hz, 1H), 1.35 (s, 9H). The XPRD pattern is as shown in FIG. 25 and is substantially the same as that of the Known Crystal Form 1 of Dabrafenib prepared in example 58a of patent document U.S. Pat. No. 7,994,185B2. The PLM plot is as shown in FIG. 26. It shows small block-shaped crystals. PSD shows: D10, D50 and D90 are 40 mum, 104 mum and 151 mum, respectively. The dynamic vapor sorption isothermal is as shown in FIG. 27. It shows: the weight change is 1.9% between 20% RH80% RH.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1195768-23-0, N-(3-(2-(tert-Butyl)-5-(2-chloropyrimidin-4-yl)thiazol-4-yl)-2-fluorophenyl)-2,6-difluorobenzenesulfonamide, and friends who are interested can also refer to it.

Reference:
Patent; Hangzhou Pushai Pharmaceutical Technology Co., LTD.; LAO, Haiping; SHENG, Xiaoxia; Sheng, Xiaohong; US2015/307484; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 33581-98-5, 4-(Hydroxymethyl)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-(Hydroxymethyl)pyrimidine, blongs to pyrimidines compound. Application In Synthesis of 4-(Hydroxymethyl)pyrimidine

To a mixture of 5-[4-(trifluoromethoxy)phenyl]-3H-l,3-benzoxazol-2-one (100 mg, 0.34 mmol), pyrimidin-4-ylmethanol (111.9 mg, 1.02 mmol) and PPh3 (177.7 mg, 0.68 mmol) in THF (6 mL) was added the DIAD (136.99 mg, 0.68 mmol) at 0 C and the mixture was stirred under N2 at 20 C for 16 hours. The mixture was concentrated to dryness, diluted with H20 (10 mL), and the mixture was extracted with EtOAc (10 mL x 2). The combined organic phase was washed with brine (10 mL), dried over Na2SC>4, filtered and the filtrate was concentrated to give the crude product. The crude product was purified by flash chromatography on silica gel (EtOAc in PE = 0% to 30% to 40% to 55%) to give the product (62.94 mg, 160.4 muiotaetaomicron, 47% yield) as colorless oil. 1H NMR OMSO-d6 400MHz deltaH = 9.09 (s, 1H), 8.79 (d, 1H), 7.74 (d, 2H), 7.63 – 7.59 (m, 2H), 7.51 – 7.41 (m, 4H), 5.30 (s, 2H). LCMS Rt = 1.27 min in 2 min chromatography, MS ESI calcd. for C19H13F3N3O3 [M+H]+ 388.1, found 387.8.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,33581-98-5, 4-(Hydroxymethyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; PRAXIS PRECISION MEDICINES , INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (244 pag.)WO2018/148745; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia