Pyrimidines

Adding a certain compound to certain chemical reactions, such as: 115617-41-9, 4,5-Dichloro-6-ethylpyrimidine, 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, 115617-41-9, blongs to pyrimidines compound. COA of Formula: C6H6Cl2N2

(1) Synthesis of 5-chloro-6-ethyl-4-[alpha-(2,2,3-trifluorobenzo-1,4-dioxane-6-yl) ethylamino] pyrimidine 0.7 g (4.0 mmol) of 4,5-dichloro-6-ethylpyrimidine which is a material compound (IIb), 0.8 g (3.4 mmol) of 1-(2,2,3-trifluorobenzo-1,4-dioxane-6-yl)ethylamine which is a material compound (IIIc) and a catalytic amount of 4-(N,N-dimethylamino)pyridine were suspended in 5 ml of triethylamine and the suspension was heated under reflux for 5 hours. After the reaction, extraction with toluene and washing with water were conducted. After drying with anhydrous sodium sulfate, toluene was removed by evaporation under reduced pressure. The resulting oily product was purified by silicagel column chromatography (Wako gel C-200, eluted with toluene:ethyl acetate = 5:1) to give 0.5 g of the desired compound as colorless oily product (indicated in Table 12 as Compound No. 41).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,115617-41-9, its application will become more common.

Reference:
Patent; UBE INDUSTRIES, LTD.; EP424125; (1991); A2;,
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Pyrimidine – Wikipedia

Electric Literature of 22536-66-9 ,Some common heterocyclic compound, 22536-66-9, molecular formula is C5H4ClN3O, 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.

A mixture of DIEA (0.111 ml, 0.635 mmol), (S)-3-(1-aminoethyl)-6-chloroquinolin-2(1H)-one II-1 (70.7 mg, 0.317 mmol), and 2-chloropyrimidine-4-carboxamide (50 mg, 0.317 mmol) in DMSO (2 ml) was heated to 110 C. for overnight, added EtOAc, washed with water, dried and concentrated. The biotage purification with 0-5% MeOH/DCM on a 25 g column afforded (S)-2-((1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl)amino)pyrimidine-4-carboxamide I-114 (49 mg, 44.9%). 1H NMR (300 MHz, DMSO-d6): delta 11.02 (br s, 1H), 8.45 (d, J=4.7 Hz, 1H), 8.00 (br, 1H), 7.79 (br, 2H), 7.72 (s, 1H), 7.47 (d, J=8.79 Hz, 1H), 7.28 (d, J=8.8 Hz, 1H), 7.02 (d, J=4.69 Hz, 1H), 5.29 (m, 1H), 1.41 (d, J=7.04 Hz, 3H).

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. 22536-66-9, 2-Chloropyrimidine-4-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Forma Therapeutics, Inc.; Lin, Jian; Ericsson, Anna; Campbell, Ann-Marie; Gustafson, Gary; Wang, Zhongguo; Diebold, R Bruce; Ashwell, Susan; Lancia, JR., David R.; Caravella, Justin Andrew; Lu, Wei; (171 pag.)US2016/83365; (2016); A1;,
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Reference 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 mixture of 4-chloro-2-methylpyrimidine (0.2 g, 1.556 mmol), (3-fluoro-4- methoxyphenyl)boronic acid (0.264 g, 1.556 mmol), and CS2CO3 (1.014 g, 3.11 mmol) in 1,4-dioxane (5 mL) and water (3 mL) was purged with nitrogen gas for 30 min. The reaction mixture was added PdCh (dppfJ-CfhCh adduct (0.127 g, 0.156 mmol) and was again purged with nitrogen gas for 10 min. The reaction mixture was heated at 80 C for 12 h. The reaction mixture was allowed to cool to room temperature and was concentrated under reduced pressure. The residue was taken up in ethyl acetate (50 mL) and water (40 mL), then the biphasic mixture was filtered through celite. The celite was washed with ethyl acetate (50 mL). The aqueous layer was separated out and the organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to afford a brown solid. The crude solid was purified by silica gel chromatography (EtOAc in pet ether) to afford 4-(3- fluoro-4-methoxyphenyl)-2-methylpyrimidine (0.128 g, 0.587 mmol, 38% yield) as a light yellow solid as an off-white color solid. LCMS (ESI) m/e 219.1 [(M+H)+, calcd for C12H12FN2O 219.1]; LC/MS retention time (method B): fe. = 0.69 min.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 4994-86-9, 4-Chloro-2-methylpyrimidine.

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 10397-13-4, 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.10397-13-4, name is 4-(4,6-Dichloropyrimidin-2-yl)morpholine, molecular formula is C8H9Cl2N3O, molecular weight is 234.08, as common compound, the synthetic route is as follows.

(4S,5R)-4-Methyl-5-thiazol-2-yl-oxazolidin-2-one (4.70 g, 20.1 mmol) was dissolved in 70 mL of DMF and cooled to 0 C. NaH (964 mg, 60% in oil, 24.1 mmol) was added under argon, and the reaction mixture was stirred for 30 minutes at 0 C. 4-(4,6-dichloropyrimidin-2-yl)morpholine (3.70 g, 20.1 mmol) dissolved in 30 mL of DMF was added, and the reaction mixture was stirred for 3 hours at 0 C., followed by stirring at RT for 2 hours. The reaction was then quenched by addition of aqueous NH4Cl, followed by dilution with EtOAc; the organic solvents were separated, washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography (80 g SiO2) using EtOAc in hexane from 0% to 100% in order to give the title compound (3.64 g, 48%). LC-MS: [M+H] 382.2, 384.1; Rt 1.10 min; (LCMS method 1). 1H NMR (400 MHz, CHCl3-d): 7.77 (d, 1H), 7.38-7.33 (m, 2H), 5.39 (d, 1H), 5.07-4.98 (m, 1H), 3.75-3.55 (m, 8H), 1.64 (d, 3H).

Statistics shows that 10397-13-4 is playing an increasingly important role. we look forward to future research findings about 4-(4,6-Dichloropyrimidin-2-yl)morpholine.

Reference:
Patent; NOVARTIS AG; Fairhurst, Robin Alec; Furet, Pascal; Kalthoff, Frank Stephan; Lerchner, Andreas; Rueeger, Heinrich; US2014/135330; (2014); A1;,
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Synthetic Route 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.

To a solution of tert-butyl (3S)-3-ethylpiperazine-l -carboxylate (0.5 g, 2.3 mmol) and 2-amino-4,6-dichloropyrimidine-5-carbaldehyde (0.45 g) in 1,4-dioxane (8.0 mL) was added DIPEA (1.2 mL, 7.0 mmol). The reaction mixture was heated at 120C overnight in a sealed Wheaton vial, then cooled and stirred at room temperature over the weekend. The solvent was removed in vacuo, and the residue was partitioned between water and DCM. The organic layers were phase separated and concentrated in vacuo to give the title compound (0.85 g, 99%) as a yellow glass. LCMS (ES+) [M+H]+ 370, RT 1.81 minutes (method 2).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 5604-46-6, 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde.

Reference:
Patent; UCB PHARMA S.A.; KATHOLIEKE UNIVERSITEIT LEUVEN, K.U.LEUVEN R&D; FORD, Daniel James; FRANKLIN, Richard Jeremy; GHAWALKAR, Anant Ramrao; HORSLEY, Helen Tracey; HUANG, Qiuya; REUBERSON, James Thomas; VANDERHOYDONCK, Bart; WO2014/96423; (2014); A1;,
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Reference of 171887-03-9, 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. 171887-03-9, name is N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide, molecular formula is C5H4Cl2N4O, 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.

5.7 mmol) and DIPEA (2.6 mL; 15.2 mmol) were added to a solutionof 3-amino-1-trityloxymethylphospholane 1-oxide 15 (1.5 g;3.8 mmol) in n-butanol (50 mL). The reaction mixture was stirredfor 40 h at 130 C and evaporated. 3-(2-Amino-6-chloropurine-9-yl)-1-trityloxymethylphospholane 1-oxide 23 was purified bychromatography on silica gel (first isocraticwash with 50% acetone/toluene, second elution with gradient of 0e10% ethanol in chloroform).ESI-MS calcd for C29H28ClN5O2P (M H) 544.2, 546.2 found544.1, 546.1.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 171887-03-9, N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide.

Reference:
Article; Pav, Ond?ej; Bud??insky, Milo?; Rosenberg, Ivan; Tetrahedron; vol. 73; 34; (2017); p. 5220 – 5228;,
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Electric Literature of 76780-96-6 ,Some common heterocyclic compound, 76780-96-6, molecular formula is C9H10Cl2N2, 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.

General procedure: To a solution of 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (4a) (0.5 g, 2.7 mmol) in 2-Propanol (6 mL) was added (S)-pyrrolidin-2-ylmethanol (0.39 mL, 4.0 mmol), DIPEA (1.39 mL, 8.0 mmol) and heated at 90 C for 1 hr. The reaction was cooled to room temperature and solid obtained was collected by filtration to afford (S)-(l-(2-chloropyrrolo[2,l-f][l,2,4]triazin-4- yl)pyrrolidin-2-yl)methanol (96a) (0.49 g, 73 % yield) as a white solid; NMR (300 MHz, DMSO-i/e): delta 7.70 (dd, J= 2.6, 1.4 Hz, 1H), 6.97 (dd, J= 4.7, 1.6 Hz, 1H), 6.80 – 6.57 (m, 1H), 5.15 (t, J = 5.7 Hz, 1H, D2O exchangeable), 4.87 (t, J= 5.7 Hz, 1H), 4.44 (d, J= 17.8 Hz, 1H), 4.05 – 3.82 (m, 1H), 3.72 – 3.39 (m, 2H), 2.22 – 1.84 (m, 4H). MS (ES+): 253.3, 255.3 (M+2); MS (ES-): 287.2, 289.2 (M+Cl).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,76780-96-6, its application will become more common.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2927-71-1, 2,4-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, Safety of 2,4-Dichloro-5-fluoropyrimidine, blongs to pyrimidines compound. Safety of 2,4-Dichloro-5-fluoropyrimidine

Under N2 atmosphere, 2,4-dichloro-5-fluoro-pyrimidine (6.3 g), commercially available, was dissolved in 1,2-dimethoxyethane (60 mL). Bis(triphenylphosphine)palladium(II) chloride (2.5 g) and 2M aqueous sodium carbonate solution (50 mL) were then added. Mixed solution was dropped at 80 C4-fluoro-1-isopropyl-2-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolane-2-yl) -1H-benzimidazole(10 g) 1,2-dimethoxyethane (50 mL) solution. The reaction was stirred at 84 C for 1 hour and the reaction was monitored by TLC. Cooled to room temperature, the resulting mixture was extracted with EtOAc (40 mL X 3) and the combined organic phases were washed with saturated brine (40 mL X 3). After drying over anhydrous sodium sulfate, the crude product was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to obtain the target Compound (5g).

The synthetic route of 2927-71-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhenjiang Sheng’an Pharmaceutical Co., Ltd.; Peng Kuai; (13 pag.)CN104892580; (2018); B;,
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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. 51940-64-8, name is Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate, the common compound, a new synthetic route is introduced below. HPLC of Formula: C7H6Cl2N2O2

To a flask charged with a solution of ethyl 2,4-dichloropyrimidine-5-carboxylate (0766) (200 mg, 0.905 mmol) and fert-butyl (4-amino-2-methylbutan-2-yl)carbamate, HCl (216 mg, 0.905 mmol) in acetonitrile (3.6 mL) was added Hiinig’s Base (474 mu, 2.71 mmol). The reaction mixture was stirred at ambient temperature under N2 (g) for 1 h. The crude material was purified using silica gel chromatography eluting with a gradient from 0 to 25% ethyl acetate in hexanes to afford ethyl 4-((3-((tert-butoxycarbonyl)amino)-3- methylbufyl)amino)-2-chloropyrimidine-5-carboxylate (248 mg, 0.641 mmol, 71 % yield) as a yellow oil. ES [MS] m/z: 387.05 [M+H]+.

The synthetic route of 51940-64-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ARAUJO, Erika M. V.; CHEN, Yan; DASGUPTA, Bireshwar; DEGNAN, Andrew P.; HILL, Matthew D.; KUMI, Godwin Kwame; MASTALERZ, Harold A.; WITTMAN, Mark D.; PEARCE, Bradley C.; ZHANG, Guifen; (172 pag.)WO2019/90198; (2019); A1;,
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Application of 55583-59-0, 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.55583-59-0, name is 2,5-Diamino-4,6-dichloropyrimidine, molecular formula is C4H4Cl2N4, molecular weight is 179.01, as common compound, the synthetic route is as follows.

In a reaction vessel, 4,6-dichloropyrimidine-2,5-diamine (500 mg, 2.79 mmol), trans-2-phenylvinylboronic acid (0.945 g, 6.42 mmol), sodium carbonate (1.48 g, Ethanol (7 mL) and distilled water (7 mL) were added to a solution of 14.0 mmol) and tetrakis (triphenyl phosphine) palladium (0) (322 mg, 0.279 mmol) in toluene (28 mL) at room temperature, and argon was added. After stirring under heating and reflux conditions for 20 hours under an atmosphere, the reaction solution was cooled to room temperature. Distilled water (8 mL) was added and stirred, and the separated aqueous layer was extracted three times with ethyl acetate (12 mL). After that, the whole organic layer is combined, saturated aqueous sodium chloride solution (12 mL) is added thereto, the mixture is stirred and washed, anhydrous sodium sulfate is added to the separated organic layer for dehydration, and the filtrate after filtration is depressurized. Concentrated. The concentrate thus obtained is purified by flash column chromatography (silica gel, n-hexane / ethyl acetate),4,6-Di ((E) -styryl) pyrimidine-2,5-diamine(0.72 g, 82% yield).

Statistics shows that 55583-59-0 is playing an increasingly important role. we look forward to future research findings about 2,5-Diamino-4,6-dichloropyrimidine.

Reference:
Patent; Microbial Chemistry Research Foundation; Kumagai, Naoya; Noda, Hidetoshi; Asada, Yasuko; Shibazaki, Masakatsu; (48 pag.)JP2019/64981; (2019); A;,
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