Pyrimidines

Synthetic Route of 4994-86-9, 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. 4994-86-9, name is 4-Chloro-2-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.

A solution of 4-chloro-2-methylpyrimidine (0.050 g, 0.389 mmol), 5-(5- bromo-2-fluoropyridin-3-yl)oxazole (0.100 g, 0.389 mmol) and hexamethylditin (0.097 mL, 0.467 mmol) in 1,4-dioxane (0.1 mL) was purged with argon for 15 min and tetrakis(triphenylphosphine)palladium (0) (0.045 g, 0.039 mmol) was added. The reaction mixture was again purged with argon for 5 min and heated in a microwave for 1 h at 110C. The reaction mixture was diluted with ethyl acetate (8 mL) and water (5 mL) and the organic layer separated. The aqueous layer was extracted again with ethyl acetate (2×5 mL). The combined ethyl acetate layers were washed with brine, dried over Na2S04, filtered, and concentrated under reduced pressure. The reaction mixture was purified by Preparative TLC (70% ethyl acetate in hexanes). The required spot was collected, dissolved 5% methanol in dichloromethane (30 mL), filtered and concentrated under reduced pressure to afford 5-(2-fluoro-5-(2-methylpyrimidin-4-yl)pyridin-3-yl)oxazole (0.070 g, 0.098 mmol, 25% yield) as an off-white solid. LCMS (ESI) m/e 257.0 [(M+H) +, calcd for C13H10FN4O, 257.1]; LC/MS retention time (method B): /R = 0.86 min.

According to the analysis of related databases, 4994-86-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (485 pag.)WO2017/59085; (2017); A1;,
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Application of 4994-86-9, 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 4994-86-9 as follows.

To a solution of N-((rac)-8-endo-3-benzyl-3-azabicyclo[3.2.1]octan-8-yl)-8-(3,4-difluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine (70 mg, 157 mumol) in methanol (1.6 mL) was added one drop of 25% aqueous hydrogen chloride solution under an atmosphere of nitrogen and stirring. The reaction was hydrogenated over night at 1 bar. The catalyst was filtered off and washed with ethanol. The solvent was evaporated under reduced pressure. The residue was dissolved in ethanol (1.6 mL). Triethylamine (47.7 mg, 65.7 muL, 471 mumol) and 4-chloro-2-methylpyrimidine (25.0 mg, 189 mumol) were added and the reaction was heated to 150 C. for 30 minutes in a microwave oven. The solvent was removed under reduced pressure after cooling to room temperature and the residue was purified by column chromatography on silica gel using a gradient from ethyl acetate to ethyl acetate/methanol (v/v 9:1) as eluent. The title compound was obtained as a light yellow solid (36 mg, 51%).MS ISP (m/e): 448.5 (100) [(M+H)+], 225.0 (80).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4994-86-9, its application will become more common.

Reference:
Patent; Baumann, Karlheinz; Green, Luke; Limberg, Anja; Luebbers, Thomas; Thomas, Andrew; US2012/225884; (2012); A1;,
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Related Products of 10070-92-5, 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 10070-92-5 as follows.

Step 1 : Pyrimidin-5-ylmethanolPyrimidine-5-carboxaldehyde (14.97 g, 138 mmol) in methanol (80 mL) at 0 0C was treated portionwise with sodium borohydride (5.24 g, 138 mmol). When the addition of sodium borohydride was complete the mixture was stirred for 1 hour at 0 0C. The mixture was quenched carefully with acetone and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 4OM, eluting with 5% methanol in dichloromethane to give pyrimidin-5-ylmethanol as a white crystalline solid.1H NMR (CDCl3): delta 9.18 (s, 1 H), 8.78 (s, 2 H), 4.81 (s, 2 H) MS: m/e 111.04 (M + H)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10070-92-5, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2009/45381; (2009); A1;,
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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. 16357-83-8, name is 4-Aminopyrimidine-5-carbaldehyde, molecular formula is C5H5N3O, 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. Formula: C5H5N3O

General procedure: To a soln. of aldehyde C-3 (1 eq) and amine BB-9 (1 eq) in THF (4 mL/mmol) were added AcOH (2 eq) and the rxn mixture was stirred for 20 min at RT. NaBH(OAc)3 (4 eq) was added portionwise and the rxn mixture was stirred at RT for a given time (see Table 34). When necessary to reach the complete reduction of the intermediate imine, NaBm (1.2 eq) can be added at 0C and the rxn mixture stirred at RT. It was quenched with a 1 M aq. soln. of NaOH and extracted with EtOAc (3x). The combined org. phases were washed with brine, dried over MgSC>4 and concentrated in vacuo. The crude was purified by CC using Hept/EtOAc/MeOH.

With the rapid development of chemical substances, we look forward to future research findings about 16357-83-8.

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; FROIDEVAUX, Sylvie; HUBLER, Francis; MURPHY, Mark; RENNEBERG, Dorte; STAMM, Simon; (97 pag.)WO2019/141808; (2019); A1;,
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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. 1044145-59-6, name is (4-Chloro-2-(methylthio)pyrimidin-5-yl)methanol. A new synthetic method of this compound is introduced below., HPLC of Formula: C6H7ClN2OS

General Procedure 5-2: 4-Chloro-2-(methylthio)pyrimidine-5-carbaldehyde[00195] A mixture of (4-chloro-2-(methylthio)pyrimidin-5-yl) methanol (9.0 g, 47 mmol) and activated MnO2 (70 g, 800 mmol, Aldrich Cat. No. 217646) in 120 mL CH2Cl2 was stirred at the room temperature for 24 hours. The mixture was filtered through Celite (Acros Celite 521, Cat.No. 206350010). The filter cake was washed with CH2Cl2 until no UV-active material was seen. The combined CH2Cl2 solution was concentrated and passed through a thin silica gel plug, using 25% EtOAc/Hexanes. The filtrate was concentrated to give an off white solid (6.37 g,71.6% yield).HPLC Rt: 5.53 min.1H-NMR (CDCl3): delta 10.32 (s, IH), 8.88 (s, IH), 2.65 (s, 3H).

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, 1044145-59-6, (4-Chloro-2-(methylthio)pyrimidin-5-yl)methanol.

Reference:
Patent; BIOGEN IDEC MA INC.; WO2008/94575; (2008); A2;,
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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;,
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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;,
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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,
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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;,
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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