Pyrimidines

A common compound: 7752-82-1, name is 5-Bromopyrimidin-2-amine,molecular formula is C4H4BrN3, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below., 7752-82-1

Conditions B (procedure using an in situ prepared boronic or boronate partner, see example 9) The halogenated substrate (1 eq), bis(pinacolato)diboron (1-2 eq), a suitable base (usually potassium acetate (1-6 eq), a suitable palladium catalyst with its ligands (usually Pd(dppf)Cl2.DCM 1-30 mol%) are stirred in a degassed solvent (usually dimethylformamide) at 60-120C for 1-16h under argon. After cooling down to room temperature, the halogenated tricyclic template (3-(7-bromo-imidazo[1,2-a]quinoxalin-4-ylamino)-propan-1-ol or 3-(7-iodo-imidazo[1,2-a]quinoxalin-4-ylamino)-propan-1-ol) (0.5 eq) is added with base (usually an aqueous solution of sodium or potassium carbonate, 1-6 eq) and a suitable palladium catalyst (usually Pd(PPh3)4 1-30 mol%). The resulting mixture is stirred under argon at 60-120C for 2 to 48h. Concentration, partition (water / ethyl acetate), extraction of the aqueous phase (ethyl acetate), reunion of the organic phases, drying over sodium or magnesium sulfate and purification by flash chromatography or prep TLC over silicagel using a suitable eluent (usually a mixture dichloromethane / methanol or cyclohexane / ethyl acetate or dichloromethane / ethyl acetate or dichloromethane / methanol / ammonia) affords the desired compound. The following examples were prepared according to these procedures. The following table provides a summary of the operating conditions. Example 20: 3-{[1-(2-aminopyrimidin-5-yl)-7-(trifluoromethyl)imidazo[1,2-a]quinoxalin-4-yl]amino}propan-1-ol [Show Image] Prepared as mentioned beforehand 1H NMR (DMSO-d6), delta (ppm): 8.45 (s, 2H), 8.05 (t, J = 5.7 Hz, 1 H), 7.82 (s, 1 H), 7.66 (d, J = 8.6 Hz, 1 H), 7.58 (s, 1 H), 7.45 (d, J = 8.6 Hz, 1H), 7.15 (s, 2H), 4.62 (t, J = 5.1 Hz, 1 H), 3.65 (q, J = 6.3 Hz, 2H), 3.54 (q, J = 6.0 Hz, 2H), 1.84 (qt, J = 6.6 Hz, 2H) ESI-MS m/z 404 (M+H)+

With the rapid development of chemical substances, we look forward to future research findings about 7752-82-1.

Reference:
Patent; Mutabilis SA; EP1972629; (2008); A1;,
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Pyrimidine – Wikipedia

271-80-7, 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. 271-80-7, name is 1H-Pyrazolo[3,4-d]pyrimidine, molecular formula is C5H4N4, 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.

520 mg (4.331 mmol) of 1H-pyrazolo[3,4-d]pyrimidine and 1.461 g (6.496 mmol) of N-iodosuccinimide were dissolved in 10 ml of DMF and the mixture was heated at 80 C. for 3 h. After cooling, the mixture was concentrated on a rotary evaporator and the residue was stirred with dichloromethane, filtered off with suction and dried under high vacuum. 569 mg (53% of theory) of the target compound were obtained. LC-MS (Method 3): Rt=1.23 min; MS (ESIpos): m/z=247 (M+H)+

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. 271-80-7, 1H-Pyrazolo[3,4-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; FOLLMANN, Markus; STASCH, Johannes-Peter; REDLICH, Gorden; GRIEBENOW, Nils; LANG, Dieter; WUNDER, Frank; PAULSEN, Holger; Huebsch, Walter; US2013/210824; (2013); A1;,
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96702-03-3 ,Some common heterocyclic compound, 96702-03-3, molecular formula is C6H10N2O2, 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.

Example 8 6-Carboxy-2-methyl-1,4,5,6-tetrahydropyrimidinium palmitate 20 g of ectoin are dissolved in 25 ml of water in a 250 ml plastic beaker with magnetic stirrer, and 36.894 g of palmitic acid are subsequently added at room temperature with stirring. This reaction mixture is stirred at room temperature for a further half an hour and subsequently evaporated to dryness in a rotary evaporator with a water bath at about 90 C., leaving a white solid. Melting point 61 C.

According to the analysis of related databases, 96702-03-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK PATENT GESELLSCHAFT; US2011/152292; (2011); A1;,
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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 591-55-9 as follows., 591-55-9

Example 4 3-Cyclopentyl-3-(4-(2-(pyrimidin-5-ylamino)thieno[3,2-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)propanenitrile T-04 Synthetic Route Preparation of Compound T-04 To a solution of compound 3 (50 mg, 0.14 mmol) and 5-aminopyrimidine (40 mg, 0.42 mmol) in isobutanol (0.5 mL) was added p-toluene sulfonic acid monohydrate (53 mg, 0.28 mmol). The mixture was heated to 110 C. and stirred for 16 hours. The mixture was then concentrated in vacuum and the residue was purified by preparation HPLC (mobile phase:acetonitrile, water (0.05% trifluoroacetic acid); gradient: 60%-90%-10%) to give compound T-04 (7 mg, yield: 12%) as a yellow solid. LC-MS (ESI): m/z=417 [M+H]+.1H-NMR (400 MHz, CD3OD) delta: 9.37 (s, 2H), 8.76 (s, 1H), 8.65 (s, 1H), 8.41 (s, 1H), 8.21 (d, J=6 Hz, 1H), 7.43 (d, J=6 Hz, 1H), 4.53 (m, 1H), 3.123.28 (m, 2H), 2.56 (m, 1H), 1.97 (m, 1H), 1.411.72 (m, 7H) ppm

The chemical industry reduces the impact on the environment during synthesis 591-55-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SHANGHAI CHEMEXPLORER CO., LTD.; XU, Zusheng; ZHANG, Nong; SUN, Qingrui; WANG, Tinghan; US2015/336982; (2015); A1;,
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137281-39-1, Adding a certain compound to certain chemical reactions, such as: 137281-39-1, 4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid, 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, 137281-39-1, blongs to pyrimidines compound.

4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic acid(64,6g 0.19mol) was added to a 1L four-neck bottle.Add 650 ml of DMF and stir to dissolve, and warm to 50 C.Add 0.38 mol of N,N-carbonyldiimidazole, and incubate at 60 C for 2 hours.Add L-glutamic acid diethyl ester (0.38 mol), and raise the temperature to 80 C for 3 hours.Evaporated to dryness under reduced pressure, and dissolved in 800 ml of dichloromethane.Pour into a mixed solution of 1600 ml of pure water and 160 ml of triethylamine, and mix and discard.The organic phase was separated and washed twice with pure water 1600 ml X 2 .Dry and evaporated to dryness, add 500 ml of absolute ethanol and stir to dissolve.72 g of water p-toluenesulfonic acid and 200 ml of absolute ethanol solution were added dropwise under reflux.After the addition, reflux reaction for 1 hour, cooling and crystallization,The mixture was suction filtered and dried to give a crude material (yield: 77.2 g (yield: 70.1%, purity: 92.3%, impurity V content: 6.52%).Add 87.2 g of the above crude product to a three-neck reaction flask.Add 350 ml of N,N-dimethylformamide,Heat to 40-45C to stir and dissolve. After total dissolution, add 700ml of absolute ethanol.The solid was slowly precipitated, cooled to room temperature, and stirred for 1-2 h.The solid obtained by filtration was 69.8 g, and the yield was 80.0%.The above-mentioned refining operation was repeated once to obtain a solid 55.4 g (purity 98.2%, impurity V includedThe amount is 0.07%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,137281-39-1, its application will become more common.

Reference:
Patent; Lunan Pharmaceutical Group Co., Ltd.; Zang Chao; Xia Mingjun; (11 pag.)CN110305136; (2019); A;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 32779-36-5, 5-Bromo-2-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, 32779-36-5, blongs to pyrimidines compound. 32779-36-5

In a pressure tube with one end sealed, add 193 mg 5-bromo-2-chloropyrimidine (1.0 mmol) and 285 mg cyclopropylamine (5.0 mmol) in 3.0 mL ethanol, and the mixture is heated to 80 ¡ãCand stirred for 3 h. The reaction mixture was cooled to room temperature, and 203 mg solid product was collected by filitration for direct useyield: 95percent).MS (ESI), m/z: 215 (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,32779-36-5, its application will become more common.

Reference:
Patent; Guangzhou Institute Of Biomedicine And Health, Chinese Academy Of Sciences; DING, Ke; WANG, Deping; PEI, Duanqing; ZHANG, Zhang; SHEN, Mengjie; LUO, Kun; FENG, Yubing; EP2594567; (2013); 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.5750-76-5, name is 2,4,5-Trichloropyrimidine, molecular formula is C4HCl3N2, molecular weight is 183.4231, as common compound, the synthetic route is as follows.5750-76-5

2,4,5-Trichloropyrimidine (250 mg, 1.36 mmol) and ferric acetylacetonate (24 mg, 0.07 mniol) were taken up in tetrahydroruran (2.7 ml) and the reaction was cooled to -78 C.Methylmagnesium bromide (0.45 ml of 3 M in THF, 1.36 mmol) was added dropwise and the mixture was stirred at -78 C for one hour. The mixture was quenched with aqueous ammonium chloride and extracted with ethyl acetate. The combined organic fractions were dried over magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure. The resulting residue was purified by Combiflash (0-10% diethylether in hexanes) to provide 2,5- dichloro-4-methylpyrimidine (99 mg, 0.61 mmol, 45 %) as a white solid. MS APCI: [M+H]+ m/z 163.0.

Statistics shows that 5750-76-5 is playing an increasingly important role. we look forward to future research findings about 2,4,5-Trichloropyrimidine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; ALTMAN, Michael, D.; ARRINGTON, Kenneth, L.; BURCH, Jason; COTE, Bernard; FOURNIER, Jean-Francois; GAUTHIER, Jacques, Yves; KATTAR, Solomon; KNOWLES, Sandra Lee; LIM, Jongwon; MACHACEK, Michelle, R.; NORTHRUP, Alan, B.; REUTERSHAN, Michael, H.; ROBICHAUD, Joel, S.; SCHELL, Adam, J.; SPENCER, Kerrie, B.; WO2011/75560; (2011); A1;,
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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 302964-08-5 as follows., 302964-08-5

62.5 mL of 3-methylbutan-l-ol was charged into 4 necked RBF at ~ 25 C. 2.5 g of N-(2-chloro-6-methylphenyl)-2-[6-chloro-2-methyl-4-pyrimidinyl) amino]-5-thiazole carboxamide and 4.12 g of 1-(3-Hydroxy)ethylpiperazine were added to the reaction mixture. The reaction mass was stirred for ~ 15 mins and then the temperature of reaction mass was raised to 135 C. After stirring the heated reaction mass (along with continuous reaction monitoring), the reaction mass was slowly cooled to 25 C, in 2 h. The cooled reaction mass was then stirred for 5 h, filtered and washed with 5.0 mL 3-methylbutan-l-ol. The material obtained after washing was suck dried for 15 min. The partially wet material obtained above was charged into a RBF and 48.75 mL 3- methylbutan-l -ol, 73 mg Diisopropylethylamine (DIPEA) and 70 mg 2-bromo ethanol were added to the reaction mixture. The reaction mixture was then heated to ~80C, wherein stirring was performed for 12 h. After stirring, the reaction mass was allowed to slowly cool down to -25 C, wherein it was again stirred for 1 h. Then the reaction mass was filtered and washed with 6.5 mL of 3-methylbutan-l-ol. The wet material obtained was unloaded, air dried for 30 min and then vacuum dried for 10 h at 65 C. The material was then allowed to cool down to 25 C and unloaded to obtain 3.0 g crystalline Form-SDI of Dasatinib having XRPD pattern according to Fig-1 , IR spectrum according to Fig-2 and DSC pattern according to Fig- 3. Yield: 83 % % purity (By HPLC): 99.42 % 1H NMR (400 MHz, DMSO) delta 11.39 (s, 1H), 9.8 (s, 1H), 8.22 (s, 1H), 7.4 (dd, 2H), 7.2 (m, 1H), 6.04 (s, 1H), 4.4 (t, 1H), 3.4 (m, 6H), 2.44 (m, 3H), 2.4 (m, 3H), 2.41 (s, 3H), 2.2 (s, 3H), 1.6 (sep, 1H), 1.3 (q, 2H), 0.85 (d, 6H).

The chemical industry reduces the impact on the environment during synthesis 302964-08-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SHILPA MEDICARE LIMITED; SRIRAM, Rampalli; PRADEEP, Pothana; SURESH, Garbapu; PRASHANT, Purohit; AKSHAY KANT, Chaturvedi; WO2015/68055; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
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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. 32779-36-5, name is 5-Bromo-2-chloropyrimidine, the common compound, a new synthetic route is introduced below. 32779-36-5

Preparation B: N- j5-(4-bromophenyl)-6- j2- j(5-bromo-2-pyrimidinyl)oxyj ethoxyj – 4-pyrimidinylj -N?- propylsulfamide (macitentan):N-(5 -(4-bromophenyl)-6-(2-hydroxyethoxy)pyrimidin-4-yl)propane- 1 -sulfamide (200 g; 0.46 mol; see Example 2 or 3) and 5-bromo-2-chloropyrimidine (117 g; 0.60 mol; 1.3 eq) were dissolved in toluene (3 L) and DMF (400 mL). The reaction mixture was warmed up to 50¡ãC and toluene (approx. 400 mL) was distilled our under reduced pressure. The mixture was cooled to 0 ¡ãC and tBuOK (156 g, 3 eq, 1.38 mol) was added portionwise. It was stirred at 20 ¡ãC for 1 h. Water (1 L) was added and the pH of the solution was adjusted to 3-5 using 33percent aq. HC1. The mixture was heated to 50¡ãC and the layers were separated. The org. phase was treated with charcoal at 50¡ãC and filtered over Celite. The filter cake was rinsed with toluene. At 50¡ãC, water (1 L) was added to the org. layer. The layers were separated. The org. layer was concentrated under reduced pressure to a total volume of 1 L and cooled to 0¡ãC. The solid obtained was filtered off It was rinsed with toluene and MeOH. The crude material was suspended in EA (1 L) and heated to 50¡ãC. 300 mL of EA were distilled out and MeOH (400 mL) was added. The suspension was cooled down to 0¡ãC. The solid was filtered off, rinsed with MeOH and dried under reduced pressure to afford the title compound as a white solid (225 g; 83percent yield).

The synthetic route of 32779-36-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; ABELE, Stefan; FUNEL, Jacques-Alexis; SCHINDELHOLZ, Ivan; WO2014/155304; (2014); 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.7752-82-1, name is 5-Bromopyrimidin-2-amine, molecular formula is C4H4BrN3, molecular weight is 173.9987, as common compound, the synthetic route is as follows.7752-82-1

c) 6-Bromo-imidazo[1,2-a]pyrimidine; 50 mmol of 5-bromo-pyrimidin-2-ylamine are dissolved in 200 mi of saturated aqueous sodium hydrogencarbonate solution. 55 mmol of chloroacetaldehyde are added to the reaction mixture and the mixture is stirred for 24 hours at 25C. The mixture is extracted with ethyl acetate (3×300 mi) and the combined extracts are dried over sodium sulphate and evaporated under reduced pressure. Flash chromatography (Si02 60F) of the residue provides the title compound which is identified on the basis of its Rf-value.

Statistics shows that 7752-82-1 is playing an increasingly important role. we look forward to future research findings about 5-Bromopyrimidin-2-amine.

Reference:
Patent; SPEEDEL EXPERIMENTA AG; WO2005/90305; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia