Tag: M.W:200-300

Electric Literature of 43024-61-9, 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.43024-61-9, name is Ethyl 7-hydroxypyrazolo[1,5-a]pyrimidine-6-carboxylate, molecular formula is C9H9N3O3, molecular weight is 207.19, as common compound, the synthetic route is as follows.

(a) 7-Hydroxypyrazolo[1,5-a]pyrimidine-6-carboxylic acid A mixture of ethyl 7-hydroxypyrazolo[1,5-a]pyrimidine-6-carboxylate (0.50g., 2.4mM) and 10% sodium hydroxide solution (5ml) was heated on a steam bath for 3 hours. The reaction mixture was cooled and acidified with acetic acid to give the required product as white crystals in 76.3% weight yield (0.33%), m.p. 319-320 C (decomposition), numax (nujol) 1740 (acid C=O) and 1675 (lactam C=O)cm-1.

The chemical industry reduces the impact on the environment during synthesis 43024-61-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Beecham Group Limited; US4081545; (1978); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 494194-61-5, 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.494194-61-5, name is 2,4-Dibromo-5-methylpyrimidine, molecular formula is C5H4Br2N2, molecular weight is 251.91, as common compound, the synthetic route is as follows.

Intermediate 32- IY2-Bromo-5 -methyl-4-pyrimidinyl)amino1 -N-( 1 -methylethvDbenzamideIn a tube were combined Intermediate 1 (4.0 g, 15.9 mmol)), Intermediate 2 (2.8 g, 15.9 mmol), isopropanol (30 mL), and di-isopropyl-ethylamine (3.7 mL, 21.2 mmol). The vessel was sealed and the mixture was heated to 110 0C for 3 days. The reaction mixture was poured onto EtOAc and water. The layers were separated and the aqueous layer was further extracted with more EtOAc. The combined organic layer was washed with brine, dried (MgSO4), filtered and concentrated. Purification by flash chromatography on silica gel (0 – 30% EtOAc/hexanes) afforded the desired product (2.8 g, 50%) as a white solid. LC-MS (ES) m/z = 349, 351 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 494194-61-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/147831; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1060815-90-8, 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. 1060815-90-8, name is 2-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H3ClIN3, 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.

-lodopropane (2.1 mL, 19.68 mmol) was added to a mixture of 2-chloro-5-iodo-7H- pyrrolo[2,3-d]pyrimidine (5.50 g, 19.8 mmol) and cesium carbonate (19.18 g, 59.04 mmol) in DMF (30 mL). The mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with EtOAc, washed with water, brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 10% EtOAc in hexane to afford the title compound as a white solid (5.5 g, 87%). 1H NMR (400 MHz, CDCl3): delta ppm 1.50 (d, 6H), 5.10 (m, 1 H), 7.36 (s, 1 H), 8.55 (s, 1 H). LCMS (System 10) Rt = 3.6 minutes MS m/z 322 [M+H]+

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 1060815-90-8, 2-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; PFIZER LIMITED; ANDREWS, Mark, David; BAGAL, Sharanjeet, Kaur; BROWN, David, Graham; GIBSON, Karl, Richard; OMOTO, Kiyoyuki; RYCKMANS, Thomas; SABNIS, Yogesh; SKERRATT, Sarah, Elizabeth; STUPPLE, Paul, Anthony; WO2014/53967; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.83255-86-1, name is 3-Bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine, molecular formula is C5H4BrN5, molecular weight is 214.02, as common compound, the synthetic route is as follows.HPLC of Formula: C5H4BrN5

Intermediate 5 (2 g, 9.34 mmol), 4-phenoxyphenylboronic acid (4 g, 18.69 mmol),Pd(PPh3)4 (531 mg, 0.46 mmol), K3PO4.3H2O (7.45 g, 28.02 mmol),Add into a 250 ml two-necked flask and add 100 ml of solvent 1,4-dioxane: water = 4:1 (v/v) to dissolve.Nitrogen protection, ultrasonically removes oxygen from the solution, and replaces the air in the device with nitrogen.The oil was heated to reflux in a 135 C oil bath, and the reaction was completed after TLC detection for 30 h.The reaction mixture was cooled to room temperature, filtered over Celite, and evaporated.Obtained a pale yellow solid of 2.23 g, a yield of 78.8%.The elution system was dichloromethane: methanol = 100:1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,83255-86-1, 3-Bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; Shandong University; Zhao Guisen; Ran Fansheng; Liu Meixia; Liu Yang; Wang Luhua; (48 pag.)CN109369654; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 149765-15-1 ,Some common heterocyclic compound, 149765-15-1, molecular formula is C11H13ClN4O, 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.

4-Chloro-2-pivaloylamino-7H-pyrrolo[2,3-d]pyrimidine 34 (150 mg, 0.59 mmol) and selectfluor (320 mg, 0.90 mmol) were placed in a round-bottom flask, followed by the addition of anhydrous MeCN (6 mL) and AcOH (0.6 mL). The mixture was then heated at 50 00 for 30 mm under N2. The mixture was then cooled by ice-water and diluted with CH2CI2 (50 mL). The organic layer was washed with sat. NaHCO3 (50 mL). The inorganic layer was separated and extracted with CH2CI2 (2 x 20 ml). The combined organic layers were dried with Na2SO4, filtered and concentrated under reduce pressure. The residue was then purified by column chromatography on silica gel (gradient DCM/MeOH, 200:1) to give 35 (48 mg, 30%) as a colorless foam. 1H NMR (300 MHz, CDCI3): 611.79 (s, 1H, NHOO), 8.25 (s, 1H, H-6), 1.39 (s, 9H, (0H3)30); 130 NMR (75 MHz, 0D013): 176.5 (NHCO), 151.3 (0-2), 150.8 (0-4), 147.8 (0-7a), 141.4 (d, 1JC,F = 248.8 Hz, 0-5), 111.2 (d, 2JC,F = 26.0 Hz, 0-6), 103.6 (d, 2JC,F = 14.9 Hz, C-4a), 40.5 (C(0H3)3), 27.7 (C(CH3)3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,149765-15-1, its application will become more common.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN; ANDREI, Graciela; DE JONGHE, Steven; GROAZ, Elisabetta; HERDEWIJN, Piet; LUO, Min; SCHOLS, Dominique; SNOECK, Robert; (81 pag.)WO2018/55071; (2018); 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. 1256353-15-7, name is 8-Bromopyrido[4,3-d]pyrimidin-4(3H)-one. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 1256353-15-7

Step B: 8-Bromopyrido[4,3-Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; ALIAGAS, Ignacio; GRADL, Stefan; GUNZNER, Janet; LEE, Wendy; MATHIEU, Simon; RUDOLPH, Joachim; WEN, Zhaoyang; ZHAO, Guiling; BUCKMELTER, Alexandre J.; GRINA, Jonas; HANSEN, Joshua D.; LAIRD, Ellen; MORENO, David; REN, Li; WENGLOWSKY, Steven Mark; WO2011/25938; (2011); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 74840-34-9, name is 4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid, molecular formula is C6H5ClN2O2S, 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. COA of Formula: C6H5ClN2O2S

A suspension of ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate (3 g, 12.9 mmol) in 40 mL methanol and 20 mL 1N NaOH solution was heated at 50° C. for 12 hrs. The reaction mixture was poured onto ice water and acidified with conc. HCl. The white creamy mixture was extracted with EtOAc. The organic fractions were dried (Na2SO4) filtered and the filtrate was concentrated to give a white solid (2 g). The solid was dissolved in 50 mL of CH2Cl2, and cooled under N2 in an ice-water bath. To the reaction was slowly added oxalyl chloride (2 mL, 19 mmol) and a drop of DMF. The reaction mixture was stirred at rt for 5 h. The reaction mixture was concentrated to give the title compound as a brown solid. This material was used in the next step without further purification.

With the rapid development of chemical substances, we look forward to future research findings about 74840-34-9.

Reference:
Patent; Player, Mark R.; Parsons, William H.; Huang, Hui; Hutta, Daniel A.; Hu, Huaping; Rinker, James; US2008/114007; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 634468-96-5, tert-Butyl 4-(pyrimidin-5-yl)piperazine-1-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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

(2) Preparation of tert-butyl 4-(2-bromopyrimidin-5-yl)piperazin-1-carboxylate Tert-butyl 4-(pyrimidin-5-yl)piperazin-1-carboxylate (2.64 g, 10 mmol) was weighed and added to acetonitrile (125 mL). N-bromobutanimide (1.78 g, 10 mmol) was added under stirring, and the mixture was stirred at 25C for 16 h. The reaction solution was concentrated. Acetic ether (100 mL) and water (100 mL) were added to separate the phases. The organic phase was concentrated and then subjected to silica gel column chromatography (dichloromethane: methanol=30:1) to get the title compound (40 mg, yield: 1.17%).

The synthetic route of 634468-96-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; WU, Frank; CHEN, Bo; (105 pag.)EP3091008; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 219915-13-6, 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 219915-13-6 as follows.

To a solution of 12 (0.89 g, 3.79 mmol) in anh. DMF (50 mL)under direct nitrogen bubble was added bis(tributyltin) (2.29 mL, 4.55 mmol) and Pd2dba3CHCl3(0.39 g, 0.38 mmol). Then, the reaction was stirred at 65 C for 2.5 h. After completion, the reaction wascooled to room temperature, and the solvent was removed in vacuo to give a black oil. The crude mixturewas resuspended in EtOAc (100 mL) and filtered over a celite pad. The filtrated was concentrated invacuo to give a brown oil. Then, the crude product was purified by flash column chromatography onsilica (0-70% EtOAc in hexanes) to give the pure product as a pale yellow oil (1.40 g, 93%); Rf = 0.64(1:1 EtOAc: Hex); 1H NMR (500 MHz, CDCl3)delta 8.46 (s, 1H), 8.11 (s, 1H), 3.65 (s, 3H), 1.20-1.31 (m, 6H),1.03-1.06 (m, 6H), 0.81-0.89 (m, 6H), 0.58-0.62 (m, 9H); 13C NMR (126 MHz, CDCl3) delta 188.5, 163.3, 158.5,128.7, 53.1, 28.9, 27.3, 13.6, 9.6; MS (ESI+) m/z calcd for C17H32N2OSn [M + H]+ 401.15, found: 401.18.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,219915-13-6, its application will become more common.

Reference:
Article; Yates, Mary K.; Chatterjee, Payel; Flint, Mike; Arefeayne, Yafet; Makuc, Damjan; Plavec, Janez; Spiropoulou, Christina F.; Seley-Radtke, Katherine L.; Molecules; vol. 24; 17; (2019);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 43024-61-9, 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. 43024-61-9, name is Ethyl 7-hydroxypyrazolo[1,5-a]pyrimidine-6-carboxylate, molecular formula is C9H9N3O3, 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.

Ethyl 7-hydroxypyrazolo[1,5-a]pyrimidine-6-carboxylate (Journal of Medicinal Chemistry, vol. 49, page 2526, 2006) (3.20 g, 15.5 mmol) was dissolved in phosphorus oxychloride (30 mL), N,N-diisopropylethylamine (5.4 mL, 30.9 mmol) was added, and the mixture was stirred with heating at 100 C. for 3 hr. After confirmation of consumption the starting materials, phosphorus oxychloride was evaporated under reduced pressure, and the residue was dissolved in ethyl acetate. The solution was added dropwise to a saturated aqueous sodium hydrogen carbonate solution under ice-cooling. To the saturated aqueous sodium hydrogen carbonate solution was added ethyl acetate, and the mixture was extracted 3 times. The combined organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.

According to the analysis of related databases, 43024-61-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KYOWA HAKKO KIRIN CO., LTD.; Yamamoto, Keisuke; Aratake, Seiji; Hemmi, Kazuki; Mizutani, Mirai; Seno, Yuko; US2014/221340; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia