Day: March 11, 2021

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
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. 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;,
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. 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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 22536-61-4, 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. 22536-61-4, name is 2-Chloro-5-methylpyrimidine. A new synthetic method of this compound is introduced below.

A 40 mL pressure vial was charged with Example 29.4 (71 mg, 0.16 mmol) which was then dissolved in DMSO (1.6 mL). To that solution was added 2-chloro-5-methylpyrimidine (83 muL, 0.80 mmol) followed by Hunig’s base (277 muL, 1.59 mmol). The vial was sealed and placed into a reaction block preheated to 100 ¡ãC. After 4 h, the reaction was cooled to RT and diluted with DCM and water. The contents of the vial were transferred into a separatory funnel and the layers were separated. The organic layer was washed with water (x3). The aqueous layer was analyzed for product and showed a large presence of product. The aqueous layer was re-extracted using 3:1 EtOAc/EtOH (x3). The combined organic layers were dried with magnesium sulfate, filtered and concentrated under reduced and purified by flash chromatography: Redi-Sep Rf Gold 12g – CV = 16.8mL, eluting with EtOAc:EtOH 3:1 (v/v) in DCM 0percent (2 CV), 0-40percent (15 CV), 40percent (5 CV) to provide Example 29.5 (54 mg, 0.10 mmol, 63 percent yield) as an orange solid. LCMS-ESI (pos.) m/z: 538.2 (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,22536-61-4, its application will become more common.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Yinhong; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HEATH, Julie Anne; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; KREIMAN, Charles; (308 pag.)WO2018/93579; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 165807-05-6 ,Some common heterocyclic compound, 165807-05-6, molecular formula is C7H11N3O2, 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.

Intermediate P: 1-(4-((2-Aminopyrimidin-4-yl)methoxy)naphthalen-1-yl)-3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)ureaHydrochloric acid (2M, 207 mL, 414 mmol) was added to 4-(dimethoxymethyl)pyrimidin-2-amine (68) (WO 2007/096764) (14.0 g, 83 mmol) and the mixture heated at 48¡ã C. for 16 hr.The mixture was cooled to RT and was neutralized with solid Na2CO3 which produced a precipitate at pH 7.The suspension was diluted with EtOAc (300 mL) and the solid removed by filtration.The organic layer was separated and the aqueous layer was extracted with 1percent MeOH in THF (4*300 mL).The organics were combined, dried and then evaporated in vacuo.The residue (ca. 4.0 g) was suspended in a mixture of MeOH (100 mL), THF (100 mL) and water (100 mL) and treated with NaBH4 (1.57 g, 41.4 mmol).After stirring for 1 hr a solution of NaOH (1M, 20 mL) was added and the mixture was allowed to stand at RT for 48 hr.The solvents were evaporated to give a yellow solid which was partitioned between water (50 mL) and EtOAc (100 mL).The solid which formed at the interface was removed by filtration and the aq layer was extracted with THF (3*300 mL) then dried and evaporated to give a yellow solid.The material was suspended in THF (100 mL) and MeOH (50 mL) and absorbed onto silica gel (20 g) and subjected to column chromatography (80 g, 15percent MeOH in DCM isocratic elution) to give (2-aminopyrimidin-4-yl)methanol (69) as an off-white solid (720 mg, 7percent): m/z 126 (M+H)+ (ES+).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 165807-05-6, 4-Dimethoxymethylpyrimidin-2-ylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Charron, Catherine Elisabeth; Fenton, Robert; Crowe, Scott; Ito, Kazuhiro; Strong, Peter; Rapeport, William Garth; Ray, Keith; US2012/244120; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1514-96-1, 4-Chloro-2-(trifluoromethyl)pyrimidine, 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, 1514-96-1, blongs to pyrimidines compound. Quality Control of 4-Chloro-2-(trifluoromethyl)pyrimidine

To a solution of (S)-2-amino-4-((3,3-difluoropropyl) (4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl) butyl)amino) butanoic acid (140 mg, 328 mumol) in THF (4 mL) and H2O (1 mL) was added 4-chloro-2-(trifluoromethyl)pyrimidine (66 mg, 361 mumol) and NaHCO3 (138 mg, 1.64 mmol) and the resulting mixture was stirred at 70 C. for 18 h and then allowed to cool to rt and then concentrated in vacuo. The crude residue was purified by reverse phase prep-HPLC to give the title compound. LCMS (ESI+): m/z=531.2 (M+H)+. 1H NMR (400 MHz, D2O) delta ppm 8.22 (br d, J=5.75 Hz, 1H) 7.49 (br d, J=7.09 Hz, 1H) 6.84 (d, J=6.24 Hz, 1H) 6.52 (br d, J=7.34 Hz, 1H) 5.91-6.26 (m, 1H) 4.72 (br s, 1H) 3.14-3.50 (m, 8H) 2.61-2.78 (m, 4H) 2.21-2.52 (m, 4H) 1.82-1.94 (m, 2H) 1.69 (br s, 4H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1514-96-1, its application will become more common.

Reference:
Patent; Pliant Therapeutics, Inc.; CHA, Jacob; DONG, Chengguo; HOM, Timothy; JIANG, Lan; LEFTHERIS, Katerina; LI, Hui; MORGANS, JR., David J.; MUNOZ, Manuel; REILLY, Maureen; ZHENG, Yajun; (232 pag.)US2019/276449; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 3764-01-0, 2,4,6-Trichloropyrimidine, 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, Product Details of 3764-01-0, blongs to pyrimidines compound. Product Details of 3764-01-0

Preparation of Compound 1-4 2,4,6-trichloropyrimidine (10 g, 54.51 mmol), phenylboronic acid (16.6 g, 136,29 mmol), Pd(PPh3)4 (3.15 g, 2.72 mmol), 2M K2CO3 (50 mL), toluen (100 mL) and ethanol (30 mL) were stirred under reflux. 4 hours later, the mixture was cooled to room temperature and extracted with EA after adding distilled water. After drying with MgSO4 and distillation under reduced pressure, Compound 1-4 (7 g, 48.%) was obtained by column separation.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3764-01-0, 2,4,6-Trichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.; AHN, Hee Choon; KIM, Nam Kyun; CHO, Young Jun; KWON, Hyuck Joo; KIM, Bong Ok; KIM, Sung Min; WO2011/99718; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 611-08-5, 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. 611-08-5, name is 5-Nitrouracil. A new synthetic method of this compound is introduced below.

General procedure: In a double-necked round-bottom flask (100 mL) wasadded a mixture consisting of nucleobase (0.01 mol),alcohol (0.012 mol), TsCl (2.86 g, 0.015), TEA (1.01 g,0.01 mol) and K2CO3 (1.38 g, 0.010 mol) in bmim[Br](10 mL). The flask was immersed in an oil bath, kept at80 C and stirred for the time when TLC indicated no furtherprogress in the conversion (Tables 4, 5, 6). The mixturewas then diluted with water (200 mL) and extracted withEtOAc (3 ¡Á 50 mL). The organic layer was dried (Na2SO4)and evaporated to afford the crude product which was purifiedby traditional column chromatography on silica geleluting with proper solvents.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,611-08-5, 5-Nitrouracil, and friends who are interested can also refer to it.

Reference:
Article; Rad, Mohammad Navid Soltani; Behrouz, Somayeh; Zarenezhad, Elham; Kaviani, Narjes; Journal of the Iranian Chemical Society; vol. 12; 9; (2015); p. 1603 – 1612;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1500-85-2, 7H-Pyrrolo[2,3-d]pyrimidin-4-amine, 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, name: 7H-Pyrrolo[2,3-d]pyrimidin-4-amine, blongs to pyrimidines compound. name: 7H-Pyrrolo[2,3-d]pyrimidin-4-amine

To a solution of 7H-pyrrolo[2,3-d]pyrimidin-4-ylamine (1.3 g, 9.7 mmol, 1.0 eq) in CHC13 (45 mL) was added NIS (2.18 g, 9.7 mmol, 1.0 eq) at rt. The solution was refluxed for 2 h. The precipitate was filtered and dried in vacuo to give 5-iodo-7H- pyrrolo[2,3-d]pyrimidin-4-ylamine (2.09 g, 83%) as a white solid.

The synthetic route of 1500-85-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; QIAN, Shawn; (346 pag.)WO2018/11628; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia