Category: pyrimidines

Synthetic Route of 2915-16-4 , The common heterocyclic compound, 2915-16-4, name is 2-Chloro-4,6-diphenylpyrimidine, molecular formula is C16H11ClN2, 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.

After introducing compound 4-1 (5.2 g, 12.3 mmol),2-chloro-4,6-diphenylpyrimidine (CAS: 2915-16-4, 3.3 g, 12.3 mmol), tetrakis(triphenylphosphine)palladium (0.71 g, 0.62 mmol), potassium carbonate (4.2 g, 30 mmol), toluene (60 mL), ethanol (20 mL), and distilled water (20 mL) into a reaction vessel, the mixture was stirred for 4 hours at 120C. After completing the reaction, the mixture was added dropwise to methanol, and the obtained solid was filtered. The obtained solid was purified by column chromatography and recrystallization to obtain compound C-75 (5.3 g, 82 %).

The synthetic route of 2915-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.; AHN, Hee-Choon; (41 pag.)WO2017/30283; (2017); A1;,
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Reference of 5413-85-4, 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 5413-85-4 as follows.

EXAMPLE 13; 6-r4-(Aminophenylmethyl)piperidin-1-yll-7,9-dihydropurin-8-one; 13A. 5,6-Diamino-4-chloropyrimidine; A mixture of 4,6-dichloro-5-aminopyrimidine (Aldrich Chemical Co.) (2.0 g, 12.2 mmol) and concentrated aqueous ammonia (20 ml) was heated to 100 0C in a sealed glass tube with vigorous stirring for 18 hours. The cooled tube was recharged with concentrated aqueous ammonia (8 ml), aggregates were broken up, and the mixture was reheated at 100 0C for a further 28 hours. The mixture was evaporated to dryness and the solids were washed with water (20 ml) and dried to give the product as yellow crystals (1.71 g, 97%). LC/MS (LCT1): R, 1.59 [M+H]+ 147, 145.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5413-85-4, its application will become more common.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; THE INSTITUTE OF CANCER RESEARCH:ROYAL CANCER HOSPITAL; CANCER RESEARCH TECHNOLOGY LIMITED; WO2007/125315; (2007); A2;,
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Reference of 213265-83-9, 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. 213265-83-9, name is 4,6-Dichloro-5-fluoropyrimidine, molecular formula is C4HCl2FN2, 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.

tert-butyl 4-[(2-{[6-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-benzim idazol-2-yl]am ino}pyridin-4-yl)methyl]piperazine-1 -carboxylate (500 mg, see Compound 01.04), 4,6- dichloro-5-fluoropyrimidine (469 mg), aqueous Na2CO3 (1.4 ml, 2.0 M) and 1,1?- bis(diphenylphosphino)ferrocene-palladium(I I )dichloride dichloromethane complex (76.4 mg) were stirred in a sealed tube in a mixture of 1,4-dioxane (10 ml) and water (2.0 ml) overnight at110?C. The mixture was then filtered over a silicone filter and concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica gel to give 556 mg (60 % purity) of the title compound.LC-MS (method 2): R = 1.36 mm; MS (ESlpos): m/z = 537 [M-H]1H..NMR (400 MHz, DMSO-d6) O [ppm]: 1.065 (16.00), 1.155 (1.74), 1.299 (1.42), 1.393 (2.88),1.414 (1.32), 2.539 (0.70), 3.334 (0.76), 3.937 (0.68), 8.097 (0.85).

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 213265-83-9, 4,6-Dichloro-5-fluoropyrimidine.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; HEINRICH, Tobias; PRINZ, Florian; LEFRANC, Julien; SCHROeDER, Jens; MENGEL, Anne; BONE, Wilhelm; BALINT, Joszef; WENGNER, Antje; EIS, Knut; IRLBACHER, Horst; KOPPITZ, Marcus; BOeMER, Ulf; BADER, Benjamin; BRIEM, Hans; LIENAU, Philip; CHRIST, Clara; STOeCKIGT, Detlef; HILLIG, Roman; (1256 pag.)WO2017/102091; (2017); A1;,
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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. 274693-26-4, name is 2-(((3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol, the common compound, a new synthetic route is introduced below. Formula: C26H32F2N6O4S

a, preparation of crude ticagreride: 56gIsopropyl ticagreIntermediate(0.1 mol, 1.0 eq) was placed in 500 mL of dichloromethane and stirred to dissolve;1.1 g of trifluoroacetic acid (0.01 mol, 0.1 eq) was added dropwise at 0-5 C.The dichloromethane solution was dripped in 30 minutes; after the dropwise addition, the reaction was carried out at 5-10 C.The reaction was monitored by TLC; after 1 hour, TLC showed the reaction of the starting material was completed and 200 mL of water was added.The pH was adjusted to 6-7 with potassium carbonate, and the aqueous layer was extracted with dichloromethane (200 mL×2). The organic phase was combined and then water (300 mL×2).Wash with saturated brine (300 mL × 2), dry over anhydrous sodium sulfate, and filter.Evaporated to dryness under reduced pressure to give 45.8 g of crude ticagrei, yield 88%b, the preparation of ticagrelor amorphous: take 10g crude ticagrei,Placed in 100 ml of tetrahydrofuran solvent, stirred, and warmed to 65-70 C,Maintain this temperature for 30 min, add 1 g of activated carbon, stir for 10 min, filter with hot heat, rinse the filter cake with tetrahydrofuran, and gradually cool the filtrate to 30-35 C with stirring.Then slowly distill off the solvent under reduced pressure, and recycle the tetrahydrofuran.Made a foamy solid, crushed, dried,9.8 g of ticagrelor amorphous product was obtained.Its X-ray powder diffraction pattern is shown in Figure 1.

The synthetic route of 274693-26-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nantong Changyou Pharmaceutical Technology Co., Ltd.; Li Zebiao; Ding Haiming; Zhang Qinghai; Li Keying; Tang Rongjie; Lin Yanfeng; (7 pag.)CN110183436; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 3993-78-0, 2-Amino-4-chloropyrimidine, 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, COA of Formula: C4H4ClN3, blongs to pyrimidines compound. COA of Formula: C4H4ClN3

A microwave vial was charged with 4-chloropyrimidin-2-amine (300 mg, 2.32 mmol), isopropylamine (828 mg, 1.2 ml, 14.0 mmol) and water (1.0 mL). The vial was flushed with argon, closed and stirred at 180 C for 30 min under microwave irradiation (caution: the pressure reached >20 bar). The reaction mixture was cooled to room temperature and extracted with dichloromethane and water. The organic layer was washed with water and the aqueous layers were back-extracted with dichloromethane. The organic layers were combined, dried over Na2S04, filtered and concentrated. The product was obtained after triturating the residue with diethyl ether and a few drops of ethyl acetate as off-white solid (282 mg, 80 ).MS: m/z = 153.4 (M+H)+

The synthetic route of 3993-78-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GOBBI, Luca; KNUST, Henner; KOERNER, Matthias; MURI, Dieter; WO2014/187762; (2014); A1;,
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Synthetic Route of 24410-19-3, 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. 24410-19-3, name is Pyrido[2,3-d]pyrimidin-4(1H)-one, molecular formula is C7H5N3O, 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.

EXAMPLE 8 4-chloro-pyrido[2,3-d]pyrimidine A mixture of pyrido[2,3-d]pyrimidin-4(3H)-one (1.471 g, 10 mM) and POCl3 (16 ml) is stirred for 1 h at reflux. The excess of POCl3 is removed under vacuum. Then dichloromethane and iced water is added and the mixture stirred until the black solid dissolves. The organic layer is separated, washed with bicarbonate solution, dried over Na2 SO4 and then evaporated to dryness. The yellow residue is recrystallized from toluene/hexane to give almost pure title compound in 70% yield. mp 137 C.

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 24410-19-3, Pyrido[2,3-d]pyrimidin-4(1H)-one.

Reference:
Patent; Pharmacia & Upjohn S.p.A.; US5965563; (1999); A;,
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Adding a certain compound to certain chemical reactions, such as: 14080-56-9, Thieno[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, 14080-56-9, blongs to pyrimidines compound. Quality Control of Thieno[2,3-d]pyrimidin-4-amine

To a solution of 100 mg (253 pmol) 6-bromo-4-hydroxy-8-methyl-4-(trifluoromethyl)-2H-spiro[cyclohexane-1 ,3-imidazo[1 ,5-a]pyridine]-1 ,5-dione (prepared according to example127a) and 42 mg (278 pmol) thieno[2,3-d]pyrimidin-4-amine (GAS-No.: 14080-56-9) in 8.2 mL 1 ,4-dioxane was added 247 mg cesium carbonate and the mixture was degassed and purged with argon several times. 15.7 mg 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, 12.9 mg 2-(dicyclohexyl-phosphino)-2,4,6-triisopropylbiphenyl, 6.1 mg palladium(ll)acetateand 24.8 mg tris(dibenzylideneacetone)dipalladium(0) were added and the mixture was stirred at 1000 for 2 hours. After concentration t he residue was purified by flash chromatography (Biotage SNAP cartridge silica 25 g, methanol: dichloromethane) and crystallization from methanol to give 42 mg (32%) of the title compound. LC-MS: m/z = 466.2 [M÷H].1HNMR (400 MHz, DMSO-d6), 6 [ppm]= 1.43 (2H), 1.83 (2H), 1.96 (2H), 2.52 (3H*), 3.46(2H), 5.99 (1H), 7.82 (1H), 7.87 (1H), 8.65 (1H), 8.70 (1H), 9.07 (1H), 10.43 (1H);*: at least partially hidden by solvent or water signal

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14080-56-9, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAYER AKTIENGESELLSCHAFT; KLAR, Ulrich; BOHLMANN, Rolf; SCHAeCKE, Heike; SUeLZLE, Detlev; MENZ, Stephan; PANKNIN, Olaf; (249 pag.)WO2018/134148; (2018); A1;,
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Application of 1312535-78-6, 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. 1312535-78-6, name is 1-(2-Chloropyrimidin-4-yl)ethanone, molecular formula is C6H5ClN2O, 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 solution of l-(2-chloropyrimidin-4-yl)ethanone 2 (1.0 g, 6.4 mmol) in acetic acid (15.0 mL), bromine (0.3 mL, 6.4 mmol) and HBr (47%, 0.7 mL, 6.4 mmol) were added. The resulting mixture was stirred at room temperature for 6h. After completion of the reaction, solvent was distilled off, and the residue obtained was washed with diethyl ether to afford INT- 27 (0.7 g, 46%) as a light brown solid. 1H NMR (400 MHz, CDC13+ DMSO-d6) delta 4.68 (s, 2H), 8.86 (d, J = 4.9 Hz, 1H), 8.80 (d, J = 4.8 Hz, 1H).

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 1312535-78-6, 1-(2-Chloropyrimidin-4-yl)ethanone.

Reference:
Patent; CELGENE AVILOMICS RESEARCH, INC.; ALEXANDER, Matthew David; MCDONALD, Joseph John; NI, Yike; NIU, Deqiang; PETTER, Russell C.; QIAO, Lixin; SINGH, Juswinder; WANG, Tao; ZHU, Zhendong; WO2014/149164; (2014); A1;,
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Application of 171887-03-9, Adding some certain compound to certain chemical reactions, such as: 171887-03-9, name is N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide,molecular formula is C5H4Cl2N4O, 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 171887-03-9.

Example 25 Preparation of (1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene 145.2 ml of a solution of (1R,4S)-1-amino-4-hydroxymethyl-2-cyclopentene (preparation similar to that in Example 14) were concentrated to 25.5 ml and filtered through Celite. The filter cake was washed with 7.5 ml of water. The filtrate contained 17.7 mmol of the above compound (HPLC) and was adjusted from pH 6.6 to pH 1 with conc. HCl and then extracted 3 times with 20 ml of isobutanol. The organic phase was discarded. The aqueous phase was adjusted to pH 12 with 30% strength NaOH and extracted 3 times with 10 ml of isobutanol. The combined organic phases were evaporated to 15 ml and 2.53 g of triethylamine were added. A solution of 2.07 g of N-(2-amino-4,6-dichloro-5-pyrimidinyl)formamide in 40 ml of ethanol was added to the mixture as in Example 24. The mixture was stirred at 80 C. for 16 h. Working up as in Example 22 resulted in 2.4 g of title compound. The yield was 85%.

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. 171887-03-9, N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Lonza AG; US6137007; (2000); A;,
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Electric Literature of 58347-49-2, 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 58347-49-2, name is 7-Chloropyrazolo[1,5-a]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 15Ethyl (4- { 8 -chloro-3 – IY 1 S)- 1 -(pyrazolof 1 ,5 -a]pyrimidin-7-ylamino)ethyllquinolin-2- yl } piperazin- 1 – vDacetateIntermediate 22 (500 mg, 1.05 mmol), EtOH (5 mL) and 2N HCl in Et2O (5 mL) were combined and stirred at r.t. for 4 days. The reaction mixture was then concentrated to give a yellow glass (526 mg, quantitative). A portion of this material (50 mg, 0.11 mmol), «-BuOH (6 mL), DIPEA (1 mL) and 7-chloropyrazolo[l,5-alpha]pyrimidine (50 mg, 0.25 mmol) were combined in a sealed tube and heated under microwave irradiation to 14O0C for 1 h. The reaction mixture was then concentrated and purified by preparative HPLC to give the title compound (39.3 mg, 72%) as a tan glass. deltaH (DMSOd6) 8.68 (IH, s), 8.47 (IH, d, J7.70 Hz), 8.14-8.09 (2H, m), 7.86-7.76 (2H, m), 7.40 (IH, t, J7.81 Hz), 6.44 (IH, d, J2.27 Hz), 6.26 (IH, d, J5.28 Hz), 5.14-5.05 (IH, m), 4.16 (2H, q, J7.10 Hz), 3.47-3.38 (2H, m), 3.42 (2H, s), 3.38-3.29 (2H, m), 3.00-2.93 (2H, m), 2.90-2.82 (2H, m), 1.90 (3H, d, J 6.69 Hz), 1.25 (3H, t, J 7.09 Hz). LCMS (ES+) 494/496 (M+H)+, RT 3.50 minutes {Method 1).

According to the analysis of related databases, 58347-49-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB PHARMA S.A.; ALLEN, Daniel, Rees; BROWN, Julien, Alistair; BUeRLI, Roland; HAUGHAN, Alan, Findlay; LANGHAM, Barry, John; MATTEUCCI, Mizio; OWENS, Andrew, Pate; RAPHY, Gilles; SHARPE, Andrew; WO2010/133836; (2010); A1;,
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