Tag: M.W:200-300

Synthetic Route 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.

A.21 (400 mg, 1.43 mmol), benzenesulphonyl chloride (272 muL, 2.13 mmol), DMAP (18 mg, 0.15 mmol) and Hnig base (350 muL, 2.17 mmol) are taken up in 10 mL DCM and stirred for 16 h at 200C. The solvent is eliminated in vacuo, the residue is purified by column chromatography (method prep. HPLC2; 10 % acetonitrile to 95 % in 12 min) and A.21-PG (HPLC-MS: tRet. = 1.98 min; MS(M+H)+ = 420; method FEC3) is obtained.

According to the analysis of related databases, 1060815-90-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ENGELHARDT, Harald; BOEHMELT, Guido; KOFINK, Christiane; KUHN, Daniel; McCONNELL, Darryl; STADTMUELLER, Heinz; WO2010/7114; (2010); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 74840-34-9, 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. 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.

2 g (6.6 mmol) of the starting material 1 ‘was dissolved in 10 ml of absolute ethanol,0.68 g of NaOH solid, 10 ml of water,Raise the temperature to reflux.After 1 h, TLC showed complete reaction.Rotate the ethanol, adjust the pH to 3 with 6NHCl,There is a lot of solid precipitation.Extraction can be obtained in white crystals 1.69g, the yield of 91.8percent.

According to the analysis of related databases, 74840-34-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; China Pharmaceutical University; Xiang, Hua; Lao, Kejing; He, Conghui; Tang, Zhengpu; Yan, Ming; Xiao, Hong; You, Qidong; (14 pag.)CN104356192; (2017); B;,
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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 31462-58-5, name is 5-Iodopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 31462-58-5

A mixture of Example 5d (0.300 g, 0.618 mmol), 5-iodopynmidine (0382 g, 1.353 mmo-i cesium carb onate (0.403 g, 1 36 mmol), dicyclohexyli^^’^-triisopropyl-tl,’- bipher^2-yl)phosphine (XPhos)(0.147 g, 0.309 mmo and palladium (Pi) acetate (0035 g, 0.154 mmol) in toluene ( 12 mL) and ter i-tutanol (3 mL) under argonwas heated in a sealed tube in a rraciowave reactor at 160 * C for 1 hour. The reaction mixture was cooled to amb ient tenperature and filtered tluDugh filter paper. The resulting filtrate was concentrated to near dryness and mixed with ethanol ( 10 mL), dioxane (20 mL j, and excess 5N s odium hydroxide solution ( 10 niL). The reaction mixture: was stirred at ant ient temperature for 1 hour and then concentrated to 5 niL and partitioned between s aturated anmionium chloride aqueous solution and ethyl acetate . The aqueous phase was extracted once more with ethyl acetate. The combined organic layers were was hed with s aturated aqueous sodium cliloride, dried over ar-hydro s mag esi m sulfate, filtered, and concentrated. The res idue was purified by flash column chromatograp ^ on s ilica gel elating with 5 % methanol in dichlorortrethane to afford the title conpou d (0.066 g, 0.1 1 mmol, 26 % yield) .

With the rapid development of chemical substances, we look forward to future research findings about 31462-58-5.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; FIDANZE, Steven D.; LIU, Dachun; MANTEI, Robert A.; MCDANIEL, Keith F.; PRATT, John; SHEPPARD, George S.; WANG, Le; BOGDAN, Andrew; HOLMS, James H.; DIETRICH, Justin D.; MARJANOVIC, Jasmina; HASVOLD, Lisa A.; DAI, Yujia; WO2014/139324; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1137576-38-5, name is 4,6-Dichloro-5-iodopyrimidine, the common compound, a new synthetic route is introduced below. HPLC of Formula: C4HCl2IN2

To the solution of 4,6-dichloro-5-iodopyrimidine (5.50 g, 20.00 mmol) (prepared according to the ref of Organic Letters; English; 11; 8; 2009; 1837 – 1840; ) in dioxane (100 mL) was slowly added the solution of tert-butyl l-(4-aminophenyl)cyclobutylcarbamate (5.2 g, 20.00 mmol) in dioxane (20 mL) and Et3N(5 ml). The reaction mixture was stirred at 80C for overnight, lc-ms indicated 4,6-dichloro-5-iodopyrimidine was completed consumed. After removed the excess solvents under the reduced pressure to get a residue, which was dissolved in Ethyl acetate (250 mL) and washed water and brine. The combined organic layer was dried over Na2S04 and then filtered, the filtrate was concentrated to give the crude product, which was further purified by flash chromatography to afford tert-butyl l-(4-(6-chloro-5-iodopyrimidin-4- ylamino)phenyl)cyclobutylcarbamate. (5.00 g 50% yield).LC/MS: (ESI+): 501 [M+l], 523 [M+Na].

The synthetic route of 1137576-38-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; SKELTON, Nicholas; GRADL, Stefan; BLAKE, James F.; GRAHAM, James M.; GUNAWARDANA, Indrani W.; HENTEMANN, Martin; MARLOW, Allison L.; TANG, Tony P.; WO2013/78254; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
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Reference of 1235451-38-3, 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 1235451-38-3 as follows.

To a mixture of compound S1 (1 equiv), AcOK (3 equiv), and compound 2 (1.2 equiv) in dioxane (10 vol) stirred at room temperature under nitrogen was added Pd(dppf)Cl2(0.05 equiv) in one portion. The resulting mixture was stirred at 90 C. under nitrogen for 3 h. After cooling the reaction mixture to room temperature and directly used in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1235451-38-3, its application will become more common.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAK, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (905 pag.)WO2017/35353; (2017); A1;,
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Pyrimidine – Wikipedia

Reference of 53557-69-0 ,Some common heterocyclic compound, 53557-69-0, molecular formula is C4H4IN3, 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 16: tert-Butyl 4-(6-aminopyrimidin-4-yI)-2-(5-chloro-2-methylphenyl)-1 H-pyrrole-1 -carboxylate (XXI) The crude tert-butyl 2-(5-chloro-2-methylphenyl)-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrrole-1 -carboxylate (392 mg, 0.94 mmol), Na2003 (250 mg, 2.36 mmol), PdC2(dppf) (77 mg, 0.094 mmol) and 6-iodopyrimidin-4-amine (311 mg, 1.41 mmol) were degassed and purged with argon and suspended in degassed 1,4-dioxane (3 mL) and water (1 mL). The reaction mixture was heated to 110 00 (oil bath temperature) for 2 h. Thesolution was diluted with EtOAc and washed with water. After drying over anhydrous Na2SO4, the organic layer was evaporated. The crude was purified by chromatography on silica gel (hexane/EtOAc 8:2) providing the title compound (220 mg, 58%).1H NMR (600 MHz, DMSQ-d6) 8.55 (s, 1 H), 7.79 (s, 1H), 7.41 (d, 1H), 7.29 (d, 1H), 7.16 (m, 1H), 6.98 (s, 1H),6.66 (s, 1H), 2.30 (s, 3H), 1.44 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,53557-69-0, its application will become more common.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; BRASCA, Maria Gabriella; BINDI, Simona; CALDARELLI, Marina; NESI, Marcella; ORRENIUS, Sten Christian; PANZERI, Achille; WO2014/19908; (2014); A2;,
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Reference of 313339-35-4, 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.313339-35-4, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid, molecular formula is C6H4Cl2N2O2S, molecular weight is 239.08, as common compound, the synthetic route is as follows.

(3) A mixture of 4,6-dichloro-5-carboxy-2-methylthiopyrimidine (prepared in Example 320(1)) 5.00 g, N,N-dimethylacetamide 50 ml, tetrahydrofuran 20 ml and sodium hydride (60%) 1.673 g is stirred for 20 minutes on an ice bath. Methanol 5 ml is dropped thereto over a period of 30 minutes and the mixture is stirred for 15 minutes. The reaction mixture is diluted with a 10% aqueous citric solution and extracted with ethyl acetate. The organic layer is washed, dried and concentrated in vacuo. The resulting solid is triturated with hexane in ice to give 4-chloro-5-carboxy-6-methoxy-2-methylthiopyrimidine as a slightly brown crystalline powder, 4.61 g. mp 179-181 C.

The chemical industry reduces the impact on the environment during synthesis 313339-35-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Yamada, Koichiro; Matsuki, Kenji; Omori, Kenji; Kikkawa, Kohei; US2004/142930; (2004); 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.60186-89-2, name is 4-Bromo-2,6-dimethoxypyrimidine, molecular formula is C6H7BrN2O2, molecular weight is 219.036, as common compound, the synthetic route is as follows.Safety of 4-Bromo-2,6-dimethoxypyrimidine

To a solution of 4-bromo-2,6-dimethoxy-pyrimidine (6.80 g, 27.94 mmol) in THF (190 mL) and diethylether (190 mL) n-butyllithium (in hexane/THF, 2.01 g, 30.74 mmol) is added dropwise with stirring at -78 C. After 4 min ethyl trifluoroacetate (4.46 g, 30.74 mmol) in THF (50 mL) is added dropwise at -78 C. The reaction mixture is stirred for 30 min at -78 C. and then the reaction is allowed to warm to room temperature slowly and stirred over night at room temperature. To the reaction mixture 1 N HCl solution is added. The resulting mixture is extracted with EA and washed with sat. sodium chloride solution and water. The organic phase is dried over sodium sulfate, filtered and the solvent is evaporated in vacuo. The residue is purified by flash column chromatography (silica gel, PE/EA=8/2) to give the product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60186-89-2, 4-Bromo-2,6-dimethoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Boehringer Ingelheim International GmbH; EICKMEIER, Christian; GERLACH, Kai; HEINE, Niklas; WEBER, Alexander; GROSS, Ulrike; US2013/225593; (2013); 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. 43024-61-9, name is Ethyl 7-hydroxypyrazolo[1,5-a]pyrimidine-6-carboxylate. A new synthetic method of this compound is introduced below., Formula: C9H9N3O3

Ethyl 7-hydroxypyrazolo[1,5-a]pyrimidine-6-carboxylate () (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.

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, 43024-61-9, Ethyl 7-hydroxypyrazolo[1,5-a]pyrimidine-6-carboxylate.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; YAMAMOTO, Keisuke; ARATAKE, Seiji; HEMMI, Kazuki; EP2543670; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 22276-97-7 ,Some common heterocyclic compound, 22276-97-7, molecular formula is C6H4BrN3O, 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.

Ste 2: (0345) (0346) Preparation of tert-butyl 5-bromo-4-oxo-3H-pyrrolo[2,3-d]pyrimidine-7(4H)-carboxylate: (0347) [00157] To a solution of 5-bromo-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (7.1 g, 33.17 mmol) in N,N-dimethyl formamide (150 mL) were added 4-dimethylaminopyridine (DMAP) (0.406 mL, 3.31 mmol)) and di-tert-butyl dicarbonate [(Boc)2O] (6.46 mL, 28.19 mmol) at 0C. The reaction mixture was stirred at 0C for 2 h. The reaction mixture was quenched with cold water (1000 mL) and stirred for 30 minutes. The precipitated solid was filtered and dried under suction to afford the title compound tert-butyl 5-bromo-4-oxo-3H-pyrrolo[2,3-d]pyrimidine- 7(4H)-carboxylate as off white solid (8.1 g, crude). Calculated (M+H): 314.1; Found (M+H): 314.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22276-97-7, its application will become more common.

Reference:
Patent; LUC THERAPEUTICS; ANDERSON, David, R.; VOLKMANN, Robert, A.; MENNITE, Frank, S.; FANGER, Christopher; (390 pag.)WO2017/100591; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia