Pyrimidines

Adding a certain compound to certain chemical reactions, such as: 51940-63-7, Ethyl 6-chloropyrimidine-4-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, Application In Synthesis of Ethyl 6-chloropyrimidine-4-carboxylate, blongs to pyrimidines compound. Application In Synthesis of Ethyl 6-chloropyrimidine-4-carboxylate

Step 1: ethyl 6-(2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-5-ylamino)pyrimidine-4-carboxylate 0.10 g (0.55 mmol) ethyl 6-chloropyrimidine-4-carboxylate and 13 muL (50 mumol) 4M HCl were added to 0.16 g (0.60 mmol) 5-amino-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1’H)-one in 1.0 mL 2-propanol. The reaction mixture was refluxed for 2 h, then cooled to RT and the resulting solid was filtered off and dried. Yield: 165 mg (54% of theory) ESI-MS: m/z=402 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,51940-63-7, Ethyl 6-chloropyrimidine-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/21500; (2011); A1;,
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Electric Literature of 1032452-86-0 ,Some common heterocyclic compound, 1032452-86-0, molecular formula is C13H10ClN3, 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.

P-Toluenesulfonic acid hydrate (22.73 g, 119.5 mmol)Was added to a solution of 3- (2-chloropyrimidin-4-yl) -1-methyl-indole (Intermediate 20, 24.27 g, 99.58 mmol)And 4-fluoro-2- (methyloxy-d3) -5-nitroaniline (Intermediate 21, 18.54 g, 99.58 mmol)In a mixture of 2-pentanol (500 mL).The resulting mixture was stirred at 105 C for 2.5 hours.Then cooled to room temperature. The resulting precipitate was collected by filtration,Washed with 2-pentanol (50 mL)Dried under vacuum to give some desired product as a yellow solid.The filtrate was cooled, the resulting precipitate was collected by filtration,Washed with 2-pentanol (10 mL). The two batches of products were combined,Grinding with CH3CN gave a solid which was collected by filtration,And dried under vacuum to give the title compound (37.4 g, 95%) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1032452-86-0, its application will become more common.

Reference:
Patent; Jiao Yuqi; (53 pag.)CN107043369; (2017); A;,
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Application of 3764-01-0, 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.3764-01-0, name is 2,4,6-Trichloropyrimidine, molecular formula is C4HCl3N2, molecular weight is 183.42, as common compound, the synthetic route is as follows.

Reference Example 13 2,6-Di-morphoIin-4-yl-f4<5'lbipyrimidinvI-2'-ylamineTo a cold solution of 2,4,6-trichloropyrimidine (16g) in methanol (20OmL) was added morpholine (15.2ml). The reaction mixture was stirred for 24 hours and the solvent was then removed in vacuo. The residue was dissolved in dichloromethane, washed with water, dried (MgSO4) and the solvent removed in vacuo. The residue was purified using flash chromatography to yield 4-(6-chloro-2-morpholin-l-yl-pyrimidin-4- yl)-morpholine.Reaction of 4-(6-chloro-2-morpholin-l-yl-pyrimidin-4-yl)-morpholine with 2- aminopyrimidine-5-boronic acid, pinacol ester using standard Suzuki conditions yielded the desired title compound. 400MHz IH NMR CDC133.64-3.66 (m, 4H, 2 x CH2), 3.7-3.86 (m, 12H, 6 x CH2), 5.22 (sbr, 2H, NH2), 6.17 (s,H, ArH), 8.89 (s, 2H, 2 x ArH).

Statistics shows that 3764-01-0 is playing an increasingly important role. we look forward to future research findings about 2,4,6-Trichloropyrimidine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; WO2009/66084; (2009); 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 3934-20-1, name is 2,4-Dichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2,4-Dichloropyrimidine

A round bottom flask containing 10 g (67.1 mmol) of the compound B-12 was charged with 9.8 g (80.5 mmol) of the compound B-11 and 2.33 g (2.01 mmol) of Pd(PPh3)4 was charged and filled with argon gas. 240 mL of toluene, 120 mL of ethanol and 120 mL of 2M K2CO3 were added and the mixture was refluxed and stirred for 4 hours. Cooled to room temperature, extracted with EA and washed with water. The obtained organic layer was dried and purified by silica column to obtain 11 g (86%) of Compound B-13.

With the rapid development of chemical substances, we look forward to future research findings about 3934-20-1.

Reference:
Patent; Rohm and Haas Electronic Materials Korea Co., Ltd.; LEE, SOO YONG; KIM, YOUNG GIL; CHO, YOUNG JUN; KWON, HYUK JOO; KIM, BONG OKH; KIM, SUNG MIN; YOON, SUNG SOO; (30 pag.)KR2015/34146; (2015); A;,
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Related Products of 3764-01-0, 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 3764-01-0, name is 2,4,6-Trichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

2-Chloro-4,6-diphenylpyrimidine 750 g (0.41 mmol) of 1,3,5-trichloropyrimidine, 100 g (0.82 mol) of phenylboronic acid and 625 ml of 4 M NaHCO3 solution are suspended in 2.5 l of ethylene glycol dimethyl ether. 2.3 g (10.23 mmol) of Pd(OAc)2 and 10.35 g (34 mmol) of P(o-Tol)3 are added to this suspension, and the reaction mixture is heated under reflux for 16 h. The mixture is subsequently partitioned between ethyl acetate and water, and the organic phase is washed three times with water and dried over Na2SO4 and evaporated in a rotary evaporator. The residue remaining is recrystallised from heptane/toluene. The yield is 43 g (0.15 mol, 38%).

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 3764-01-0, 2,4,6-Trichloropyrimidine.

Reference:
Patent; Merck Patent GmbH; Pflumm, Christof; Buesing, Arne; Parham, Amir Hossain; Fortte, Rocco; Heil, Holger; Stoessel, Philipp; Mujica-Fernaud, Teresa; US2013/53558; (2013); 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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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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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: 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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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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