Day: June 25, 2021

Synthetic Route of 1195-08-0, 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.1195-08-0, name is 2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde, molecular formula is C5H4N2O3, molecular weight is 140.1, as common compound, the synthetic route is as follows.

General procedure: To a stirred solution of free amine ester (1 equiv was previously isolated: 1 equiv of the corresponding hydrochloride with 1.3 equiv K2CO3, in a mixture of AcOEt/H2O during 1h. It was washed with water and the organic fase evaporated), in toluene (2 mL) was added 5-formyluracile (1 equiv, 0.5 mmol). After that, dipolarophile (1.0 equiv, 0.5 mmol) and AgOAc (5 mol%). The solvent was removed under reduced pressure. The crude mixture was filtrated through Celite with warm EtOH to furnish the corresponding product.

Statistics shows that 1195-08-0 is playing an increasingly important role. we look forward to future research findings about 2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde.

Reference:
Article; Selva, Elisabet; Castello, Luis M.; Mancebo-Aracil, Juan; Selva, Veronica; Najera, Carmen; Foubelo, Francisco; Sansano, Jose M.; Tetrahedron; vol. 73; 49; (2017); p. 6840 – 6846;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 58536-46-2, 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.58536-46-2, name is 4-(4-Bromophenyl)-2,6-diphenylpyrimidine, molecular formula is C22H15BrN2, molecular weight is 387.27, as common compound, the synthetic route is as follows.

250ml four-necked flask, under a nitrogen atmosphere,Add 0.01 mol of raw material A8, 0.025 mol of raw material B4,0.04 mol of sodium tert-butoxide, 2 x 10-4 mol of Pd2(dba)3,2×10-4 mol of tri-tert-butylphosphine, 150 ml of toluene,Heat reflux for 24 hours, sample the plate, reaction is complete;Cool naturally, filter, rotate the filtrate, pass the silica gel column,Got the target product 78,Purity 97.8%, yield 64.3%.

Statistics shows that 58536-46-2 is playing an increasingly important role. we look forward to future research findings about 4-(4-Bromophenyl)-2,6-diphenylpyrimidine.

Reference:
Patent; Jiangsu March Optoelectric Technology Co., Ltd.; Cai Xiao; Li Chong; Zhang Zhaochao; Tang Dandan; Zhang Xiaoqing; (53 pag.)CN107586299; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 5018-38-2, 4,6-Dichloro-5-methoxypyrimidine, 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, 5018-38-2, blongs to pyrimidines compound. Quality Control of 4,6-Dichloro-5-methoxypyrimidine

Example 1 4-(6-Chloro-5-methoxy-pyrimidin-4-yloxy)-piperidine-1-carboxylic acid isopropyl ester A 500 ml, 4-necked flask equipped with thermometer, mechanical stirrer and condenser with gas inlet was purged with N2 and charged with NaH (4.4 g; 0.1 1 mol) and N,N-dimethylformamide (50 ml). In a separate flask were dissolved 4-hydroxy-piperidine-1-carboxylic acid isopropyl ester (18.7 g; 0.1 mol) and 4,6-dichloro-5-methoxy-pyrimidine (17.9 g; 0.1 mol) in DMF (50 ml; 0.5 L/mol). The prepared solution was then added dropwise to the above- mentioned NaH/DMF suspension while maintaining the temperature between – 10 and -5C. The resulting mixture is then stirred for one hour, then allowed to warm up to room temperature and stirred for 17 hours. Water (300 ml; 3 L/mol) was added dropwise while maintaining the temperature between 15-300C by cooling with tap water. Heptane (125 ml; 1.25 L/mol) was added and the resulting mixture was heated up to 55C. The aqueous layer was discarded; the organic layer was cooled down to 200C and stirred for another 3-2Oh. The resulting precipitate was filtered and dried in vacuum at 500C for 2Oh to yield the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5018-38-2, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LI, Xun; WELLS, Ken; BRANUM, Shawn; DAMON, Sandra; WO2010/135506; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 5177-27-5, 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 5177-27-5 as follows.

To 2,4-dichloro-pyrimidin-5-ylamine (3.03 g, 18.1 mmol)In n-BuOH (40 mL)(1S,2S)-2-Amino-cyclopentanol hydrochloride (2.50 g, 17.2 mmol) was added to the stirred suspensionAnd DIEA (9.20 mL, 51.8 mmol).The mixture was stirred at 130 C for 4 h.Then the reaction mixture under reduced pressure and EtOAc was concentrated and the crude product was triturated in the heptane and filtered to yield a solid BT-1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5177-27-5, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BAKONYI,JOHANNA; BRUNETTE,STEVEN RICHARD; COLLIN,DELPHINE; HUGHES,ROBERT OWEN; LI,XIANG; LIANG,SHUANG; SIBLEY,ROBERT; TURNER,MICHAEL ROBERT; WU,LIFEN; ZHANG,QIANG; (169 pag.)TW2018/38997; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 3177-20-6, Methyl 2,4-dichloropyrimidine-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, SDS of cas: 3177-20-6, blongs to pyrimidines compound. SDS of cas: 3177-20-6

Alternatively, instead of the hydrazone linkage describe above, the compounds may have an amide linkage (see Scheme I below). The synthesis consists of 3 steps. First, to a stirred solution of 4-(2-hydroxyethyl)morpholine (B) (2.8 g, 21.3 mmol) in anhydrous THF (45 mL) at 0 0C, sodium hydride, 60percent dispersion in mineral oil, (0.9 g, 22.5 mmol) is added in three portions under nitrogen purge. Ice-bath was removed and a mixture is stirred at room temperature for 20-30 minutes. The mixture is cooled to 0 0C and added drop-wise (using syringe or dropping funnel) under nitrogen purge to a solution of methyl 2,4-dichloropyrirnidine carboxylate (A) (4.03 g, 19.4 mmol) in anhydrous THF (35 mL) at 0 0C. The resultant solution is stirred for 30 minutes at 0 0C, followed by 30 minutes at room temperature. It is then quenched carefully with ice-water (115mL) and diluted with ethyl acetate (115 mL). Organic layer is separated, water layer extracted once with ethyl acetate, combined ethyl acetate extracts are washed with brine and dried over anhydrous sodium sulfate. Concentration, followed by column chromatography with gradient eluation (hexane : ethyl acetate, 1:1; hexane : ethyl acetate,l:2; ethyl acetate; dichloromethane-acetone-methanol, 3:1:01) affords 3 fractions: first (0.56 g, 9.5percent ) – mostly isomer C, second (1.28 g, 21.8percent)- a mixture of C and D, and byproduct (E), third (0.7 g, 11.9percent) – mostly isomer (D). EPO In the second step, a solution of compound C (0.6 g, 2 mmol), 5-amino-2,3- dimethylindole (F) (0.32 g, 2 mmol) and DIPEA (0.28 g, 2.2 mmol)in dioxane is heated at reflux for two hours. Ethyl acetate and water are added to the concentrated reaction mixture, water layer extracted with ethyl acetate, combined ethyl acetate extracts washed with brine and dried over anhydrous sodium sulfate. Product G (0.64 g, 75percent) is isolated by column chromatography with gradient eluation (ethyl acetate; dichloromethane- acetone-methanol, 3:1:01).In the same manner compound D is converted into product H.Compounds H is then converted into their corresponding amides (I) using appropriate amines following general procedure for amide formation.To a stirred mixture of ester (1 mmol) and amine (1.05 mmol) in toluene (3.2 mL)., 2 M solution of trimethylaluminum in toluene (1.6 eq) is added drop-wise under nitrogen purge. The reaction mixture is stirred until gas evolution halted, and then mixture is micro waved at 120 0C for 5-7 minutes (Emrys Optimizer). To the reaction mixture were added IN NaOH solution and dichloromethane, organic layer separated, washed with water, brine and dried over anhydrous sodium sulfate. Flash column chromatography purification affords about 65-75percent of a desired amide (I).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3177-20-6, Methyl 2,4-dichloropyrimidine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; SYNTA PHARMACEUTICALS CORP.; WO2006/53109; (2006); 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.22715-27-1, name is 2,5-Diaminepyrimidine, molecular formula is C4H6N4, molecular weight is 110.12, as common compound, the synthetic route is as follows.SDS of cas: 22715-27-1

EXAMPLE 73. Synthesis of N-(2-Amino-Pyrimidin-5-vn-2-ChIoro-S-(3- Trifluoromethvl-BenzovlaimnoVBenzamide (Compound XXXV)XXXV[0254] A solution of intermediate 1 (Example 2) (380 mg, 1.11 mmol) in DCM was charged with CDMT (233 mg, 1.33 mmol), and NMM (0.3 mL, 2.73 mmol). After 1 hr of stirring, 2,5-diaminopyrimidine (121 mg, 1.10 mmol) was added and the solution was allowed to stir for 48 h. The mixture was concentrated and purified by HPLC to afford the title compound as a white solid (350 mg, 73%).[0255] 1H NMR (500 MHz, DMSOd6): delta 7.59 (d, J= 8.8 Hz, IH), 7.81 (t, J= 7.9 Hz, IH), 7.93 (dd, J= 8.8 Hz, J= 2.5 Hz, IH), 8.00 (d, J= 7.8 Hz, IH), 8.02 (d, J= 2.7 Hz, IH), 8.28 (d, J= 8.0 Hz, IH), 8.32 (s, IH), 8.54 (s, 2H), 10.45 (s, IH), 10.71 (s, IH). MS (ES+): m/z 436.0 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22715-27-1, 2,5-Diaminepyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; TARGEGEN, INC.; WO2008/8234; (2008); A1;,
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 22536-61-4, name is 2-Chloro-5-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. name: 2-Chloro-5-methylpyrimidine

Preparation example 1: Preparation of 5-(bromomethyl)-2-chloropyrimidine 2-chloro-5-methylpyrimidine (12.86 g, 0.1 mol) was dissolved in carbon tetrachloride (300 mL), and N-bromobutanimide (25.72 g, 0.14 mol) and benzoyl peroxide (1.29 g, 5 mmol) were added under stirring. The resultant mixture was heated to reflux by oil bath, and was cooled to room temperature after reacting for 8 h. The mixture was filtrated under suction. The filtrate was concentrated and then subjected to silica gel column chromatography (petroleum ether: acetic ether=1:1) to get the title compound (8.7 g, yield: 42percent).

With the rapid development of chemical substances, we look forward to future research findings about 22536-61-4.

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

Electric Literature of 4595-59-9, 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 4595-59-9 as follows.

General procedure: In the reaction tube with a magnetic bar was added the solution of aryl bromides (0.5 mmol) and phenylboronic acid (91 mg, 0.75 mmol), NaOH (24 mg, 0.6 mmol), complex 1 (0.0001-0.02 mol%, dissolved in DMA) and ethanol (3 mL). After stirred for the required time in the preset conditions, the reaction mixture was cooled to room temperature, and then quenched by 1 mL brine and 3 mL water, and extracted with ethyl acetate (3×5 mL). The combined organic layer was dried over anhydrous MgSO4 and the filtrate was concentrated to dryness under reduced pressure. The crude products were purified by column chromatography (petroleum ether, ethyl acetate) on silica gel.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4595-59-9, its application will become more common.

Reference:
Article; Wu, Qinxu; Wu, Leilei; Zhang, Lei; Fu, Haiyan; Zheng, Xueli; Chen, Hua; Li, Ruixiang; Tetrahedron; vol. 70; 21; (2014); p. 3471 – 3477;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 287714-35-6, 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. 287714-35-6, name is Methyl 2-chloropyrimidine-5-carboxylate, molecular formula is C6H5ClN2O2, 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 suspension of (5,6,7, 8-tetrahydroimidazo[1,2-a]pyrazin-2-yl)-methanol hydrochloride (V, 0.35 g, 1.85 mmol) was added potassium carbonate (0.51 g, 3.71 mmol) at 0 C and stirred at that temperature for 5 min. Then, 2-chloro-pyrimidine-5-carboxylic acid methyl ester (0.38 g, 2.22 mmol) was added and the resulting mixture was stirred at room temperature for 15 h. The reaction mixture was quenched with ice and the solvent was evaporated to get the residue. Water was added and precipitate formed was filtered,ashed with water and n-hexane to afford the pure product as an off-white solid (VI, 0.36 g, 68%). LC-MS m/z calcd for Ci3Hi5N503, 289.1 ; found 290.1 [M+H]+.

According to the analysis of related databases, 287714-35-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JUBILANT BIOSYS LIMITED; RAJAGOPAL, Sridharan; HALLUR, Mahanandeesha S.; DEWANG, Purushottam; MURUGAN, Kannan; KUMAR C.H., Durga Prasanna; IYER, Pravin; MULAKALA, Chandrika; SIVANANDHAN, Dhanalakshmi; NAIR, Sreekala; ZAINUDDIN, Mohd.; TANTRY, Subramanyam Janardhan; GAJENDRAN, Chandru; RAJAGOPAL, Sriram; (334 pag.)WO2017/195216; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 28485-17-8, 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. 28485-17-8, name is 5-Carbethoxyuracil, molecular formula is C7H8N2O4, 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 2. A mixture of ethyl 2,4-dioxo-l,2,3,4-tetrahydropyrimidine-5-carboxylate obtained in step 1 (8.5 g, 46.2 mmol, 1.0 eq), N,N-dimethylbenzenamine (1.12 g, 9.24 mmol, 0.2 eq), POCl3 (21.25 g, 138.6 mmol, 3.0 eq) in benzene (300 mL) was stirred at 9O 0C under a nitrogen atmosphere for 8 h. The reaction mixture was allowed to cool to room temperature and throw into ice (300 g). The mixture was extracted by EtOAc (2×300 mL). The combined organic phases were washed (brine), dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel chromatography (PE/EtOAc=500:l to 15:1 as eluent) to afford ethyl 2,4- dichloropyrimidine-5-carboxylate (3.83 g, 37%) as white solid. LC-MS (m/z) =220.9 [M+H]+.

According to the analysis of related databases, 28485-17-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WANG, Tiansheng; HANZELKA, Brian; MUH, Ute; BEMIS, Guy; ZUCCOLA, Harmon, J.; WO2011/19405; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia