Pyrimidines

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. 720-01-4, name is Ethyl 4-chloro-2-trifluoromethylpyrimidine-5-carboxylate, molecular formula is C8H6ClF3N2O2, 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. Product Details of 720-01-4

(3,5-Bis-trifluoromethyl-ben2yl)-(5-morpholin-4-yl-pyrimidin-2-yl)-[2- (4 , 4 , 5 , 5 -tetramethyl- [ 1 , 3 , 2] dioxaborolan- 2 -yl) – 5 – trifluoromethyl-benzyl] – amine (250mg) is dissolved in 1,4-dioxane (5ml) and thereto are added ethyl 4-chloro-2-trifluoromethyl-pyrimidine-5-carboxylate (140mg), [I5 I1- bis(diphenylphosphino)ferrocene]dichloropalladium dichloromethane complex (30mg) and cesium carbonate (177mg), and the mixture is stirred under nitrogen atmosphere at 80C overnight. The reaction solution is cooled to room temperature, and thereto are added water and ethyl acetate and the insoluble materials are removed by filtration through Celite. The filtrate is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane : ethyl acetate = 9: 1-?4: 1) to give ethyl 4-(2-{[(3,5-bis- trifluoromethyl-benzyl) – (5-morpholin-4-yl-pyrimidin-2 -yl) -amino] -methyl}- 4-trifluoromethyl-phenyl)-2-trifluoromethyl-pyrimidine-5-carboxylate (199mg). MS (m/z): 783 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 720-01-4.

Reference:
Patent; TANABE SEIYAKU CO., LTD.; WO2007/88996; (2007); A1;,
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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.13544-44-0, name is 2,4-Dichloro-5-iodopyrimidine, molecular formula is C4HCl2IN2, molecular weight is 274.88, as common compound, the synthetic route is as follows.Recommanded Product: 2,4-Dichloro-5-iodopyrimidine

To a solution of 2,4-dichloro-5-iodopyrimidine (5.50 g, 20.00 mmol) in dioxane (100 mL) was slowly added a solution of tert-butyl l-(4-aminophenyl) cyclobutylcarbamate (5.2 g, 20.00 mmol) in dioxane (20 mL) and triethylamine (5 ml). The reaction mixture was stirred at 80 C overnight. Lc-ms indicated 2,4-dichloro-5-iodopyrimidine was completed consumed. The solvents were removed under reduced pressure to produce a residue, which was dissolved in ethyl acetate (250 mL). The mixture was washed with brine. The combined organic layer was dried over Na2S04 and then filtered. The filtrate was concentrated to give the crude product, which was purified by flash chromatography to afford tert-butyl l-(4-(2-chloro-5- iodopyrimidin-4-ylamino)phenyl)cyclobutylcarbamate. (5.00 g, 50% yield). LC/MS: (ESI+): 501 [M+l]+ , 503 [M+l]+ .

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13544-44-0, 2,4-Dichloro-5-iodopyrimidine, and friends who are interested can also refer to it.

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;,
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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 2435-50-9, name is Pyrimidine-4-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 2435-50-9

A mixture of N1 -methyl-4-trifluoromethyl-benzene-1 , 2- diamine (0.29 g) , pyrimidine-4-carbaldehyde (0.20 g) , sodium sulfite (0.48 g) , and D F (8 ml) was stirred at 80 C for 2 hours, then at 100 C for 2.5 hours. After standing to cool the reaction mixture to room temperature, to the reaction mixture, saturated aqueous ammonium chloride solution was added, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.20 g of the compound of the formula: (Compound 2 ) .

With the rapid development of chemical substances, we look forward to future research findings about 2435-50-9.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; TAKAHASHI, Masaki; TANABE, Takamasa; NOKURA, Yoshihiko; WO2012/74135; (2012); A1;,
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Application of 941685-26-3, 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. 941685-26-3, name is 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below.

233 mg (0. 82mmo 1) 2- [(4-chloropyrrolo [2,3 -d]pyrimidin-7-yl)methoxy] ethyl-trimethylsilane was dissolved in 4 ml dry THF and cooled down to -78 C and 500 jiL (1.8 M stocksolution, 0.9 mmol, 1.1 eq.) LDA was added. The mixture was stirred under nitrogen for40 minutes at -78 C then 208 mg iodine (0.82 mmol, 1 eq.) was added and allowed to warm to r.t. It was stirred for 40 minutes, then water was added. The solution was extracted with EEO (2 x 15 ml), combined organic phase was dried (magnesium sulfate) and evaporated. The residue was purified by flash chromatography (Eluent: heptane-EEOgradient).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,941685-26-3, 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; LES LABORATOIRES SERVIER; VERNALIS (R&D) LIMITED; KOTSCHY, Andras; WEBER, Csaba; VASAS, Attila; MOLNAR, Balazs; KISS, Arpad; MACIAS, Alba; MURRAY, James Brooke; LEWKOWICZ, Elodie; GENESTE, Olivier; CHANRION, Maia; DEMARLES, Didier; (105 pag.)WO2017/212012; (2017); A1;,
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Related Products of 5604-46-6, 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. 5604-46-6, name is 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde. A new synthetic method of this compound is introduced below.

The compound of formula () (2.4g, 12.5mmol) and 37.5mL THF was added 12.5mL H 2 O mixed solution Were heated to 50 C, was added hydrazine hydrate (1.5g, 25.2mmol), 50 C After stirring for 5min, stirred at room temperature for 20min, was added 100mL of ice water stirring 15min, after unscrew the THF was filtered and dried under vacuum to give a yellow solid 2.06 g, yield 97.6%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5604-46-6, 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai Jiao Tong University; Shen, YuMei; Wei, XiaoFei; Gong, Bing; Hu, Yu; Jiang, Yu; Zhao, XioaDong; Shao, Zhifeng; Li, Xiaowei; Wu, XinYan; Tang, Daonian; Liu, Yazhi; (28 pag.)CN103804447; (2016); B;,
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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 29274-24-6, name is 5-Chloropyrazolo[1,5-a]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 29274-24-6

To a solution of 5-chloropyrazolo[1,5-a]pyrimidine (295 mg, 1.92 mmol) in DCM (10 mL) was added (chloromethylene)dimethyliminium chloride (1.06 g, 6 mmol). The reaction was stirred at 45 C. overnight, and concentrated in vacuo. The residue was dissolved in saturated NaHCO3 aqueous solution (50 mL) and the resulted mixture was then extracted with EtOAc (50 mL¡Á3). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound as a light yellow solid (380 mg, 100%). MS (ESI, pos. ion) m/z: 182.2 [M+H]+

With the rapid development of chemical substances, we look forward to future research findings about 29274-24-6.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; Xi, Ning; US2014/234254; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 213265-83-9, 4,6-Dichloro-5-fluoropyrimidine, 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, Quality Control of 4,6-Dichloro-5-fluoropyrimidine, blongs to pyrimidines compound. Quality Control of 4,6-Dichloro-5-fluoropyrimidine

Preparation 1 – 4-Chloro-5-fluoro-6-vinyl pyrimidine 5 A mixture of 4,6-dichloro-5-fluoropyrimidine (5.0 g, 30.0 mmol, 1.0 equiv) and tributyl(vinyl)tin (10.4 g, 33.0 mmol, 1.1 equiv) in dichloromethane(50 mL)was degassed with a stream of with nitrogen for 10 minutes. Bis(triphenylphosphine) palladium(ll) chloride (0.53 g, 0.75 mmol, 0.025 equiv) was added. The resulting mixture was degassed with a stream of nitrogen for an additional 15 minutes and heated at10 reflux for 72 hours. The reaction mixture was cooled to room temperature and quenched with an aqueous potassium fluoride solution (2 M, 75 mL, 5 equiv). The resulting mixture was allowed to stir for 2 hours and filtered through Celite. The filtrate was poured intoseparatory funnel and separated. The organic layer was washed with water (20 mL) and saturated brine (20 mL), dried over sodium sulfate, filtered and concentrated under15 reduced pressure at 20C. The resulting crude product was purified on an AnaLogix (SF40-i 1 5g) column. The gradient utilized for the purification was 10 minutes isocratic pentane, followed by a 20 minutes ramp to 5% diethyl ether in pentane. The pure fractions were combined and concentrated under reduced pressure at 20 C to give 4- chloro-5-fluoro-6-vinylpyrimidine (3.0 g, 63% yield).20+ 1Mass spectrum (positive mode): m/z 158.0 (M ). H NMR (300 MHz, CDCI3): oe (ppm)8.71 (s, 1H), 6.99 (m, 1H), 6.75 (dd, J=17.4 Hz, 1.8 Hz, 1H), 5.90 (dd, J=i0.5 Hz, 1.5 Hz, 1H). 19F NMR (282 MHz, CDCI3): oe 133.88 (s).

The synthetic route of 213265-83-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER IRELAND PHARMACEUTICALS; BURRELL, Adam, James, Musgrave; O’NEILL, Padraig, Mary; PETTMAN, Alan, John; WO2014/60900; (2014); A1;,
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Related Products of 5604-46-6, 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 5604-46-6, name is 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

Example 1; 2-Amino-4-[methoxyimino-(4-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-7-yl)-methyl]-thieno[2,3-d]pyrimidine-6-carboxylic acid ethylamide; Step 1; 2-Amino-4-chloro-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester; To a stirred mixture of 2-amino-4,6-dichloro-5-formyl-pyrimidine (available from Bionet Research Intermediates, UK) (5.Og 1 eq.) and potassium carbonate (9.0 g; 2.5 equiv.) in acetonitrile (160ml) at ambient temperature was added ethyl-2-mercaptoacetate (2.86 ml; 1.0 equiv.). The resulting mixture was stirred at reflux for three hours. After cooling, the solvents were removed in vacuo and the residue partitioned between ethyl acetate and water, the phases separated and the organic phase washed with saturated aqueous sodium chloride solution. Phases were separated and the organic phase was dried over Na2SO4 then filtered and filtrate solvents removed in vacuo. The crude product was purified by column chromatography on silica gel, eluting with ethyl acetate and hexanes, to afford 2-Amino-4-chloro- thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester as a yellow powder (60%).LC-MS: RT = 2.371 minutes, m/z = 258.0 [M+H]+ (Total run time = 3.5 minutes)

According to the analysis of related databases, 5604-46-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERNALIS R & D LTD; CANCER RESEARCH TECHNOLOGY LTD; THE INSTITUTE OF CANCER RESEARCH; WO2006/79789; (2006); A1;,
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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. 18592-13-7, name is 6-(Chloromethyl)pyrimidine-2,4(1H,3H)-dione, molecular formula is C5H5ClN2O2, 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. Product Details of 18592-13-7

Referential Example 1 Synthesis of 5-chloro-6-chloromethyluracil To a suspension of 6-chloromethyluracil (163 g) in acetic acid (500 ml), sulfuryl chloride (120 ml) was added dropwise at room temperature over 20 minutes, followed by stirring at the same temperature for 3 hours. The reaction mixture was poured into ice water (500 ml), and a crystallized matter was collected by filtration, whereby 182.3 g of the title compound were obtained (yield: 92%). Melting point: 225 C. min. (decomposed). NMR spectrum (DMSO-d6) delta: 4.46(2H,s), 11.57(1H,s), 11.71(1H,s).

With the rapid development of chemical substances, we look forward to future research findings about 18592-13-7.

Reference:
Patent; Taiho Pharmaceutical Co., Ltd.; US5744475; (1998); A;,
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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. 51957-32-5, name is 4-Chloro-5-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C5H5ClN2

General procedure: EtOH (1.9 mL) was added into a mixture of Intermediate 1J (100 mg, 0.24 mmol), B2(OH)4 (64 mg, 0.71 mmol), XPhos-Pd-G2 (19 mg, 0.024 mmol), XPhos (23 mg, 0.048 mmol), and KOAc (70 mg, 0.71 mmol). The reaction was degassed with N2 and stirred at 80C for approximately 55 minutes. After cooling to room temperature, methyl 4- chloronicotinate hydrochloride (64 mg, 0.31 mmol) and K2C03 (1.8 M, 400 mu, 0.71 mmol) were added respectively. The reaction was degassed with N2 again, stirred at 85C for approximately 3 hours, and cooled to room temperature. The reaction was filtered through celite and washed with EtOAc (3X). The combined organic layers were washed with brine (IX), dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0 – 100% EtOAc/Hexanes) to afford the title compound (70 mg, 61%). LCMS (method A): m/z 479.5 (M+H)+. 1H NMR (CDCI3) delta 9.00 (s, IH), 8.72 (d, IH), 7.82 (d, IH), 7.77 (d, IH), 7.55 (t, IH), 7.47 (t, IH), 7.29 (m, 2H), 7.21-7.14 (m, 3H), 5.18 (s, IH), 3.77 (s, 3H), 1.68 (s, 6H).

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, 51957-32-5, 4-Chloro-5-methylpyrimidine.

Reference:
Patent; VENENUM BIODESIGN LLC; HUANG, Chia-Yu; SHI, Dongchuan; KULTGEN, Steven G.; MCGUINNESS, Brian F; LETOURNEAU, Jeffrey J.; COLE, Andrew G.; BEASLEY, James R.; (358 pag.)WO2018/5801; (2018); A2;,
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