Category: pyrimidines

Synthetic Route of 4595-60-2, 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 4595-60-2 as follows.

General procedure: A dry, argon-flushed Schlenk flask equipped with a magnetic stirring bar and a septum was charged with spiro compound 1 (0.38 mmol. 1.0 equiv) in anhyd THF (3 mL) and cooled to -78 C for 10 min. 2.48M n-BuLi in hexane (0.42 mmol, 1.1 equiv) was added and the mixture was stirred at -78 C for 1 h until GC analysis of reaction aliquots showed full consumption of the starting material. 1 M ZnCl2 in THF solution (0.46 mmol, 1.2 equiv) was added and the mixture was stirred at -78 to 0 C for 1 h. An aryl bromide or acid chloride 10d-o(0.30 mmol, 0.8 equiv) and Pd(PPh3)4 (0.015 mmol, 0.05 equiv, 5mol%) were added and the mixture was stirred at 50 C for 3-6 h. The mixture was quenched with sat. aq NH4Cl solution (5 mL) and extracted with EtOAc (4 × 15 mL). The combined organic phases were dried (Na2SO4) and concentrated in vacuo. The crude residue obtained was purified by flash column chromatography (silica gel pre-neutralizedwith Et3N, isohexane-EtOAc) to give the analytically pure spiroproduct 11d-o.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4595-60-2, its application will become more common.

Reference:
Article; Dhayalan, Vasudevan; Alcaniz, Fernando Rabasa; Werner, Veronika; Karaghiosoff, Konstantin; Knochel, Paul; Synthesis; vol. 47; 24; (2015); p. 3972 – 3982;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1979-96-0, 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. 1979-96-0, name is 4,6-Dichloro-2-(methylthio)-5-nitropyrimidine, molecular formula is C5H3Cl2N3O2S, 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.

Method VII, Part 1: 4-Amino-6-chloro-2-methylthio-5-nitropyrimidine: To a solution of above dichloride (2.46 g, 10.2 mmol) in THF (34 mL) at -20 C. was added Et3N (3.14 mL, 22.5 mmol) followed by a solution of NH3 (2.0 M in MeOH, 5.4 mL, 11 mmol). The mixture was stirred while warming to 0 C. for 1.5 h (LC/MS indicated consumption of starting materials. Some bis-addition is observed). The reaction mixture was taken forward without work-up.

According to the analysis of related databases, 1979-96-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gilead Sciences, Inc.; US2010/143301; (2010); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 75833-38-4, 2-Chloropyrimidine-4-carbonitrile, 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, 75833-38-4, blongs to pyrimidines compound. name: 2-Chloropyrimidine-4-carbonitrile

2-Chloropyrimidine-4-carbonitrile (22.42 mg, 0.161 mmol), Na2C03 (134 muEpsilon, 0.268 mmol), (S)-3-(4-(6-amino-5-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2- yl)pyridin-3-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (65mg, 0.134 mmol), and dichloro(l,l-bis(diphenylphosphinoferrocene))palladium(II) (10.94 mg, 0.013 mmol) were combined in dioxane (268 mu) and stirred at 100C in a microwave oven for 1 hour. LC-MS indicated good conversion to desired product. After cooling to room temperature, the reaction mixture was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g), eluting with a gradient of 0 % to 10 % MeOH in DCM, to provide (S)-2-(2-amino-5-(4- (5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)phenyl)pyridin-3-yl)pyrimidine-4- carbonitrile as yellow solid. NMR (500 MHz, DMSO-d6) delta 10.56 (s, 1H), 8.83 (d, J = 4.70 Hz, 1H), 8.59 (d, J= 2.67 Hz, 1H), 8.13 (d, J= 8.44 Hz, 1H), 8.06 (dd, J= 2.14, 6.30 Hz, 1H), 7.66 (d, J= 8.66 Hz, 2H), 7.58 (d, J= 8.87 Hz, 2H), 7.49 (d, J= 4.49 Hz, 1H), 7.35 – 7.42 (m, 2H), 7.23 – 7.35 (m, 3H), 5.49 (s, 1H), 1.66 (s, 3H), 0.92 (s, 3H). m/z (ESI) 463.8 (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,75833-38-4, its application will become more common.

Reference:
Patent; AMGEN INC.; BREGMAN, Howard; BUCHANAN, John, L.; CHAKKA, Nagasree; DIMAURO, Erin; GUNAYDIN, Hakan; GUZMAN PEREZ, Angel; HUA, Zihao; HUANG, Hongbing; HUANG, Xin; MARTIN, Matthew, W.; PATEL, Vinod; WO2013/134079; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
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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 1111638-74-4, name is 4-(3-Iodo-1H-pyrazol-4-yl)-2-(methylthio)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C8H7IN4S

Example B-49: Preparation of 3-(4-(1-(1-hydroxy-2-methylpropan-2-yl)-3-(5-methoxypyridin-3-yl)- 1H-pyrazol-4-yl)pyrimidin-2-ylamino)propanenitrileB-49-1 B-49-2B -49-4 B-49Preparation of methyl 2-(3-iodo-4-(2-(methylthio)pyrimidin-4-yl)-1H-pyrazol-1-yl)-2- methylpropanoate (B-49-1)B-49-1To a mixture compound A (60 g, 0.19 mol) and methyl 2-bromo-2-methylpropanoate (102 g, 0.57 mol) in DMF (400 ml_) was added freshly ground potassium carbonate (65 g, 0.47 mol) in one portion. The reaction mixture was stirred at 8O0C for 18 hours. LC-MS indicated the reaction was complete. The reaction mixture was filtered and the filtrate was partitioned between ethyl acetate (1200 mL) and brine (300 mL). The aqueous layer was extracted with EtOAc (2 x 500 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by silica gel chromatography using 5-30% EtOAc in petroleum ether as eluent to give compound B-49-1 (62 g, 78%) as syrup, which solidified on standing.

With the rapid development of chemical substances, we look forward to future research findings about 1111638-74-4.

Reference:
Patent; PFIZER INC.; WO2009/16460; (2009); A2;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 6214-65-9, 5-Acetyluracil, 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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

Example P41; benzofuro[3,2-d]pyrimidine-2,4(1H,3H)-dione:To a stirred solution of 3-amino-2,3-dihydrobenzofuran-2-carboxamide (82.2 mg, 0.461 mmol, 1.0 eq.) in anhydrous toluene (8 mL) under an inert atmosphere was added oxalyl chloride (70.2 mg, 553 mumol, 1.2 eq.) in a dropwise manner. The resulting mixture was heated to reflux (115 0C) for 4 hours whereupon it was cooled and stirred for a further 16 hours. The crude reaction mixture was concentrated to half of its volume and filtered to give a colorless solid (41.5 mg, 45 %).Analytical data:1H-NMR (400 MHz, DMSO): delta 11.80 (s, 1 H), 8.50-7.20 (m, 4H).13C-NMR (125 MHz, DMSO): delta 162.2, 157.0, 152.7, 134.6, 128.4, 125.9, 125.1 ,123.5, 121.1 , 112.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6214-65-9, 5-Acetyluracil, and friends who are interested can also refer to it.

Reference:
Patent; UNIVERSITY OF BASEL; CMILJANOVIC, Vladimir; CMILJANOVIC, Natasa; GIESE, Bernd; WYMANN, Matthias; WO2010/52569; (2010); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 933702-55-7, 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. 933702-55-7, name is 2-Chloropyrimidine-5-carbaldehyde, molecular formula is C5H3ClN2O, 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.

(3) Add 5.4 g (37.5 mmol) of 2-chloropyrimidin-5-formaldehyde, 5.0 g (31.2 mmol) of intermediate 2 and 30 ml of methanol to a 150 ml single-mouth bottle, stir and mix well, and add 0.4 g of ethylene to the mixture. The amine is heated to reflux 12, and the reaction is completed. After cooling the reaction product to room temperature, it was extracted with dichloromethane, washed with water, dried over anhydrous sodium sulfate, filtered, and evaporated.Dichloromethane was removed by distillation to give a crude material (yield: petroleum ether) to give the product 5-(2-chloropyrimidine-5-)methylene-4-phenylfuran-2 (5H) – Ketone 6.7 g, yield 62.8%.

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 933702-55-7, 2-Chloropyrimidine-5-carbaldehyde.

Reference:
Patent; Yangtze University; Wu Qinglai; Cai Jinlong; (28 pag.)CN109761939; (2019); A;,
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Pyrimidine – Wikipedia

Synthetic Route of 89581-38-4, 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. 89581-38-4, name is Methyl 5-bromopyrimidine-2-carboxylate, molecular formula is C6H5BrN2O2, 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.

j0445j To a round bottom flask were added sequentially methyl 5-bromopyrimidine-2- carboxylate (0.83 g, 3.82 mmol), di-tert-butyl( (3,6-dimethoxy-2-[2,4,6-tris(propan-2- yl)phenyl]phenyl})phosphane (0.02 g, 0.04 mmol) and caesium carbonate (1.74 g, 5.35 mmol). These solids were mixed, then evacuated under vacuum and purged with nitrogen three times. Methanol (0.61 g, 19.12 mmol) was then added to this flask via a syringe. lila separate flask was weighed methanesulfonato(2-(di-tert-butylphosphino)-3 ,6-dimethoxy- 2?,4?,6?-tri-i-propyl- 1,1 Lhiphenyl)(2?amino_1, I ?-biphenyl-2-yl)palladium(II) (0.03 g, 0.04 mmol), which was evacuated and purged with nitrogen twice. Dioxane (3.8 mL) was added to this flask and the flask agitated until a greenish solution resulted; this solution was then transferred via syringe to the first flask. The resulting reaction mixiure was heated to 50 C for 4 hours. The reaction mixture was cooled, diluted with ethyl acetate and filtered. The velatiles were evaporated and the residue purified by FCC (silica, 50-100% ethyl acetate in heptane) to give the title compound 0.25 g (32% yield) as an off-white solid. SH NMR (500 MHz, Chloroform) X.54 (s, 2H), 4M5 (s, 3H), 4AM (s, 3H). Tr(METCR1673) = 0.48 mm, (ESj (M–H) 169.

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 89581-38-4, Methyl 5-bromopyrimidine-2-carboxylate.

Reference:
Patent; CHDI FOUNDATION, INC.; DOMINGUEZ, Celia; WITYAK, John; BARD, Jonathan; KISELYOV, Alex; BROWN, Christopher, John; GALAN, Sebastien, Rene Gabriel; PRIME, Michael, Edward; GILES, Paul, Richard; GADOULEAU, Elise, Luciennen Paulette; KRUeLLE, Thomas, Martin; CLARK-FREW, Daniel; JOHNSON, Peter, David; SCHAERTL, Sabine; HERRMANN, Frank; GRIMM, Steffen, Kaspar; KAHMANN, Jan, Dirk; SCHEICH, Christoph; COE, Samuel; HAYES, Sarah; (271 pag.)WO2016/33445; (2016); A1;,
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Synthetic Route of 32779-36-5, 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.32779-36-5, name is 5-Bromo-2-chloropyrimidine, molecular formula is C4H2BrClN2, molecular weight is 193.4291, as common compound, the synthetic route is as follows.

Preparation B; N-[5-(4-bromophenyl)-6-[2- [(5-bromo-2-pyrimidinyl)oxy] ethoxy]-4-pyrimidinyl]-N’-propylsulfamide (macitentan); N-(5-(4-bromophenyl)-6-(2-hydroxyethoxy)pyrimidin-4-yl)propane-1-sulfamide (200 g; 0.46 mol; see Example 1) 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°C and toluene (approx. 400 mL) was distilled our under reduced pressure. The mixture was cooled to 0 °C and tBuOK (156 g, 3 eq., 1.38 mol) was added portionwise. It was stirred at 20 °C for 1 h. Water (1 L) was added and the pH of the solution was adjusted to 3-5 using 33percent aq. HCl. The mixture was heated to 50°C and the layers were separated. The org. phase was treated with charcoal at 50°C and filtered over Celite. The filter cake was rinsed with toluene. At 50°C, 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°C. 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°C. 300 mL of EA were distilled out and MeOH (400 mL) was added. The suspension was cooled down to 0°C. 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).

Statistics shows that 32779-36-5 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-chloropyrimidine.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; ABELE, Stefan; FUNEL, Jacques-Alexis; SCHINDELHOLZ, Ivan; WO2015/4265; (2015); A1;,
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Pyrimidine – Wikipedia

Related Products of 3764-01-0 ,Some common heterocyclic compound, 3764-01-0, molecular formula is C4HCl3N2, 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.

To the solution of compound 6a (10 mmol) and Et3N (24 mmol) in EtOH (50 mL), morpholine (20 mmol) was added dropwise at 0 C. The mixture was stirred at room temperature for 24 h and a white solid was precipitated. Concentrated the reaction mixture to remove EtOH. The residue was dissolved in CH2Cl2, washed with water and brine. The organic layer was concentrated to give the residue, which was purified using flash chromatography (petroleum ether/EtOAc, 7:1) to yield a white solid, yield 78%. 1H NMR (400 MHz, Chloroform-d) delta 5.87 (s, 1H), 3.96-3.18 (m, 16H). 13C NMR (101 MHz, CDCl3) delta 163.54, 160.88, 160.60, 91.19, 66.84 (2CH2), 66.51 (2CH2), 44.44 (2CH2), 44.37 (2CH2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3764-01-0, its application will become more common.

Reference:
Article; Li, Wenlu; Sun, Qinsheng; Song, Lu; Gao, Chunmei; Liu, Feng; Chen, Yuzong; Jiang, Yuyang; European Journal of Medicinal Chemistry; vol. 141; (2017); p. 721 – 733;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 6972-27-6, 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 6972-27-6 as follows.

General procedure: A solution of the above crude N-substituted benzamidine (10.0mmol) in DMF (5 mL) was added dropwise at 0 C to a solution of NaH (20.0 mmol) in DMF (5 mL) and stirred for 30 min. A solution of 1,3-dimethyl-6-chlorouracil (5.0 mmol) in DMF (5 mL) was added dropwise at 0 C and the reaction mixture was stirred at 80 C overnight. Sat. aq NH4Cl (20 mL) was added at 0 C and the mixture was extracted with EtOAc (5 × 10 mL). The combined organic phases were washed with H2O (2 × 10 mL) and brine (1 × 10 mL), and dried (MgSO4). The solvent was removed under reduced pressure and the crude material was purified by silica gel column chromatography to give 1a-e,h,k-o.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6972-27-6, its application will become more common.

Reference:
Article; Shimizu, Maki; Hayama, Noboru; Kimachi, Tetsutaro; Inamoto, Kiyofumi; Synthesis; vol. 49; 18; (2017); p. 4183 – 4190;,
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