Pyrimidines

Adding a certain compound to certain chemical reactions, such as: 36847-10-6, 4,6-Dibromopyrimidine, 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, 36847-10-6, blongs to pyrimidines compound. name: 4,6-Dibromopyrimidine

10292] In this example, a method of synthesizing an organic compound of one embodiment of the present invention, 5,5?- (4,6-pyrimidinediyldi-3, 1 -phenylene)bis-5H-benzothieno[3, 2-c]carbazole (abbreviation: 4,6mBTcP2Pm) (structural formula (112)), is described. Note that a structure of 4,6mBTcP2Pm is shown below. 10293] Into a 100-mE three-neck flask were put 0.75 g (3.2 mmol) of 4,6-dibromopyridine, 3.3 g (6.9 mmol) of2-[3-(5H- benzothieno[3,2-c]carbazol-5-yl)phenyl]-4,4,5,5-tetram- ethyl-1,3,2-dioxaborol ane, and 96mg (0.32 mmol) of tris(2- methylphenyl)phosphine. The air in the flask was replaced with nitrogen. To this mixture were added 7 mE of a 2M aqueous solution of potassium carbonate, 16 mE of toluene, and 5 mE of ethanol. The mixture was degassed by being stirred under reduced pressure. To this mixture, 14mg (0.062 mmol) of palladium(II) acetate was added. The mixture was stirred at 90 C. under a nitrogen stream for 16 hours.10294] After that, a precipitated solid was collected by suction filtration. Chloroform was added to this solid, and irradiation with ultrasonic waves was performed; then, a solid was collected by suction filtration. Toluene was added to this solid, and irradiation with ultrasonic waves was performed. A solid was collected by suction filtration to give 1.9 g of a brown solid, which was the object of the synthesis, in a yield of 79%.10295] The synthesis scheme of the above synthesis method is shown below in (D-1).10296] By a train sublimation method, 1.9 g of the obtained brown solid was purified. In the purification by sublimation, the brown solid was heated at 360 C. under the conditions where the pressure was 3.0 Pa and the argon flow rate was 5.0 mE/mm. Afier the purification by sublimation, 0.76 g ofyellow solid was obtained at a collection rate of 40%.10297] By a train sublimation method, 0.76 g of the obtained yellow solid was again purified. In the purification by sublimation, the yellow solid was heated at 360 C. under the conditions where the pressure was 3.0 Pa and the argon flow rate was 5.0 mE/mm. Afier the purification by sublimation, 0.58 g of a yellow solid was obtained at a collection rate of 90%.10298] Analysis results by nuclear magnetic resonance (?H-NMR) spectroscopy of the obtained yellow solid are described below. FIGS. 32A and 32B are ?H-NMR charts. The results show that the organic compound of one embodiment of the present invention, 4,6mBTcP2Pm (structural formula (112)), was obtained.10299] ?H-NMR (CDC13, 300 MHz): oe (ppm)=7.43-7.55 (m, 12H), 7.77-7.84 (m, 411), 7.99 (d, J=8.7 Hz, 2H), 8.16- 8.20 (m, 5H), 8.28-8.33 (m, 4H), 8.44 (s, 2H), 9.36 (d, J=0.9 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,36847-10-6, its application will become more common.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; Mitsumori, Satomi; OHE, Yuko; HAMADA, Takao; (66 pag.)US2016/75718; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 13223-25-1, 2-Chloro-4,6-dimethoxypyrimidine, 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, Computed Properties of C6H7ClN2O2, blongs to pyrimidines compound. Computed Properties of C6H7ClN2O2

Preparation of methyl 2-(4,6-dimethoxy-2-pyrimidinyloxy)-3-methylbenzoate 4.38 g (25 mmol) of 2-chloro-4,6-dimethoxypyrimidine, 4.17 g (25.0 mmol) of methyl 2-hydroxy-3-methylbenzoate and 0.66 g (6.3 mmol) of sodium methanesulfinate were heated in the presence of 5.17 g (37.5 mmol) of potassium carbonate in 25 ml of N,N-dimethylformamide to 120 C. with stirring. After 8 hours, the solvent was removed in a rotary evaporator at 60 C./20 mbar. The residue was taken up in 30 ml of water and 30 ml of dichloromethane. After the organic phase had been separated off, the aqueous phase was again extracted with 20 ml of dichloromethane. The combined organic phases was washed with water, dried over magnesium sulfate and evaporated. The residue was purified by chromatography on a silica gel column (eluent hexane/ethyl acetate 4:1). The title product was obtained from the product fraction in a yield of 5.23 g (65.8 percent of theory) (GC content 96 percent). The melting point of the compound was 73.8 to 79.1 C. Other data concerning the title compound was: 1 H NMR (DMSO, MHz 400)delta=7.75 (1 H, d); 7.58 (1 H, d); 7.30 (1 H, t); 5.95 (1 H, s); 3.75 (6 H, s); 3.62 (3 H, s); 2.17 (3 H, s). GC/MS: 304; 273, 245

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13223-25-1, 2-Chloro-4,6-dimethoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Lonza AG; US5840892; (1998); A;,
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Pyrimidine – Wikipedia

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. 2450-08-0, name is Methyl pyrimidine-4-carboxylate, molecular formula is C6H6N2O2, 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. name: Methyl pyrimidine-4-carboxylate

Step C: S-Oxo-S-pyrimidin^-yl-propionic acid ethyl ester : To a solution of the product of Preparation 2, Step B (5.8 g, 42 mmol), in EtOAc (180 ml) was added 1M potassium ferf-butoxide in THF (85 ml, 85 mmol) in four portions, with mechanical stirring. The reaction was refluxed for 40 hr. Water (200 ml) was added and layers separated. The aqueous was washed with EtOAc (2 X 100 ml). The aqueous was acidified with cone. HCI to pH 2-3 then extracted with CHCI3 (3 X 100 ml). The organics were combined, washed with brine, dried over sodium sulfate, and concentrated to give the title compound as an orange solid (7.07g 86%). (Mixture of keto and enol form) Keto: 1H-NMR(CDCI3) delta ppm 12.22 (s, 1 H), 9.23(s, 1H), 8.89 (d, J=4.Q8 Hz, 1 H), 7.83 – 7.85 (m, 1 H), 7.26(s, 1H), 6.46(s, 1H), 4.30 (q, J=7.05 Hz, 2 H), 1.34 (t, J=7.26 Hz, 3 H).

With the rapid development of chemical substances, we look forward to future research findings about 2450-08-0.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/23239; (2008); A1;,
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Related Products of 1224288-92-9, 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 1224288-92-9 as follows.

To a mixture of methyl 3-fluoro-5-((2R,4S)-4-fluoropyrrolidin-2-yl)benzoate (400.00 mg, 2.24 mmol, 1.00 eq) in dioxane (50.00 mL) was added DIPEA (868.45 mg, 6.72 mmol, 3.00 eq) and5-chloropyrazolo [1 ,5-ajpyrimidine-3 -carbonitrile (540.00 mg, 2.24 mmol, 1.00 eq). The mixturewas stirred at 100C for 16 hrs. The mixture was concentrated to give the crude product. The crude product was purified by column chromatography on silica gel (PE:EtOAc = 10:1-3:1) to give methyl 3-((2R,4S)- 1 -(3-cyanopyrazolo[ 1 ,5-ajpyrimidin-5-yl)- 4-fluoropyrrolidin-2-yl)-5- fluorobenzoate (650.00 mg, 1.70 mmol, yield: 75.89%) as a yellow oil. ?H-NMR (400 MHz, CD3OD) 5 ppm 8.30-8.24 (m, 1H), 6.94-6.83 (m, 2H), 5.64 (t, 1H, J = 9.2 Hz), 5.41 (d, 1H, J = 52.0Hz), 4.48-4.3 8 (m, 2H), 3.97 (s, 3H), 2.79-2.69 (m, 1H), 2.20-2.06 (m, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1224288-92-9, its application will become more common.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; WENGLOWSKY, Steven, Mark; MIDUTURU, Chandrasekhar, V.; BIFULCO, Neil, Jr; KIM, Joseph, L.; (91 pag.)WO2017/87778; (2017); A1;,
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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. 91717-22-5, name is 2-Amino-4-piperidino-6-methylpyrimidine, molecular formula is C10H16N4, 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. Recommanded Product: 91717-22-5

General procedure: Briefly, 4-methyl-6-(piperidin-1-yl)pyrimidin-2-amine 1 (0.30 mmol), benzaldehyde 2a (0.30 mmol), 10 equiv of dimethyl malonate 3a (3 mmol), and chiral catalyst Q4(10 mol%) were added to capped vials at 60C and stirred for 36 h. After completion of the reaction, as observed by TLC, the mixture was directly purified by column chromatography on silica gel (EtOAc/hexane=8:1), affording the product (R)-4a. However, the product (S)-4a was obtained using the Q5 catalyst. Enantiomeric excess of the product was determined by HPLC analysis using a Chiralpak IA column.

With the rapid development of chemical substances, we look forward to future research findings about 91717-22-5.

Reference:
Article; Bai, Song; Liu, Shan; Zhu, Yunying; Zhao, Kunhong; Wu, Qin; Synlett; vol. 29; 14; (2018); p. 1921 – 1925;,
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Application of 583878-42-6, 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.583878-42-6, name is Ethyl 4-chloro-6-methyl-2-(methylthio)pyrimidine-5-carboxylate, molecular formula is C9H11ClN2O2S, molecular weight is 246.71, as common compound, the synthetic route is as follows.

[00248] To a solution of ethyl 4-chloro-6-methyl-2-(methylthio)pyrimidine-5-carboxylate (65 g) in THF (1000 niL) and triethylamine (110 niL, 0.81 mole) was added ethylamine (2.0 M in THF, 0.81 mole) at 0 0C. This reaction mixture was stirred at room temperature overnight and then solvents were removed on a rotary evaporator. H2O was added and the mixture extracted with ethyl acetate several times. Solvents from the combined organic layers were removed on a rotary evaporator affording 58 g (86% yield) of ethyl 4-(ethylamino)-6- methyl-2-(methylthio)pyrimidine-5-carboxylate. This material was used as such without further purification.

The chemical industry reduces the impact on the environment during synthesis 583878-42-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; EXELIXIS, INC.; WO2008/127678; (2008); A1;,
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Pyrimidine – Wikipedia

Application of 1152475-42-7, Adding some certain compound to certain chemical reactions, such as: 1152475-42-7, name is 7-Bromo-2-chlorothieno[3,2-d]pyrimidine,molecular formula is C6H2BrClN2S, 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 1152475-42-7.

Step 6: 3-(2-chlorothieno[3,2-d]pyrimidin-7-yl)benzenamine 7-Bromo-2-chlorothieno[3,2-d]pyrimidine (3.645 g, 14.61 mmol) was dissolved in dioxane (44 mL) and 2.0 N sodium carbonate (22 mL, 43.83 mmol) and 3-aminophenylboronic acid (2 g, 14.61 mmol) were added. After flowing nitrogen to the mixture solution for 10 minutes, Pd2(PPh3)Cl2 (615 mg, 0.88 mmol) and t-ButylXphos (558 mg, mmol) were added. The reaction mixture solution was stirred at 90 C. for 6 hours and filtered with celite. The filtrate was diluted with ethyl acetate and washed with brine. The organic layer was concentrated by drying with magnesium sulfate. Purification by chromatography (20% ethyl acetate/hexane) yielded the target compound (2.8 g, 73% yield). 1H NMR (400 MHz, CDCl3) delta 9.14 (s, 1H), 8.10 (s, 1H), 7.31 (s, 1H), 7.27 (d, J=6.4 Hz, 2H), 6.74 (m, 1H), 3.85 (br, 2H), MS m/z: 262.04, 264.03 [M+1].

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. 1152475-42-7, 7-Bromo-2-chlorothieno[3,2-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Korea Institute of Science and Technology; US2012/277424; (2012); A1;,
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Pyrimidine – Wikipedia

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 16019-33-3, name is 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde. A new synthetic method of this compound is introduced below., Recommanded Product: 16019-33-3

To a solution of 2-(4,6-dichloropyrimidin-5-yl)acetaldehyde (2.80 g, 14.66 mmol) and ((1S,4S)-4-aminocyclohexyl)methanol (Step AS.3, 14.66 mmol) in anhydrous EtOH (30 mL) was added DIEA. The reaction was stirred in a sealed vial at 60 C for 20 h.The reaction was diluted with EtOAc (150 mL), washed with water (10 mL), saturated aqueous NaCI (10 mL), dried over Na2S04 and evaporated. The residue was purified by flash chromatography (Si02, EtOAc: hex/0- 100%) to give the title compound as a yellow solid. MS m/z 266.1 (M+H+) (Method M).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 16019-33-3, 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde.

Reference:
Patent; NOVARTIS AG; IRM LLC; CHEN, Bei; FAIRHURST, Robin, Alec; FLOERSHEIMER, Andreas; FURET, Pascal; GUAGNANO, Vito; JIANG, Songchun; LU, Wenshuo; MARSILJE, Thomas, H.; MCCARTHY, Clive; MICHELLYS, Pierre-Yves; STAUFFER, Frederic; STUTZ, Stefan; VAUPEL, Andrea; WO2011/29915; (2011); A1;,
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Reference of 5767-35-1, 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 5767-35-1 as follows.

Example 11 : Synthesis of (Z)-3-(3-(3,5-bis(trifluoromethyl)phenyl)-lH-l,2,4-triazol- -yl)-N’-(6-chloropyrimidin-4-yl)acrylohydrazide (1-12).A 25-mL, 3-necked, round-bottomed flask was charged with a solution of (Z)-3-(3-(3,5-bis(trifluoromethyl)phenyl)-lH-l,2,4-triazol-l-yl)acrylic acid (0.5 g) and 4-chloro-6- hydrazinopyrimidine (0.20 g, 1.0 eq.) in EtOAc (5.0 mL). The mixture was cooled at -40 C and treated with T3P (2.3 mL, 2.5 eq.) and DIPEA (0.98 mL, 4.0 eq.). TLC analysis (using 5% MeOH-CH2Cl2 as eluent) showed that the starting material was consumed after 30 min. The reaction mixture was then diluted with CH2O2, washed with water, dried over anhydrous Na2S04, filtered and concentrated under reduced pressure (25 C, 20 mmHg) to afford crude material that was subjected to preparative TLC purification using 5% MeOH-CH2Cl2 with as the mobile phase. This afforded 250 mg (yield: 36.74%) (Z)-3-(3-(3,5- bis(trifluoromethyl)phenyl)- 1 H- 1 ,2,4-triazol- 1 -yl)-N’-(6-chloropyrimidin-4-yl- )acrylohydrazide. 1H NMR (400 MHz, DMSO-d6), delta= 10.59 (br s, exchangeable, 1H), 9.85 (br s, exchangeable, 1H), 9.52 (s, 1H), 8.50 (s, 2H), 8.38 (s, 1H), 8.27 (s, 1H), 7.52-7.55 (d, 1H, J= 10.4 Hz), 6.69 (s, 1H), 6.05-6.08 (d, 1H, J= 10.4 Hz); LCMS: Calculated forCI7HII C1F6N70 (M+H)+ 478.76; found: 478.09 (RT 2.79 min, purity: 97.51%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5767-35-1, its application will become more common.

Reference:
Patent; KARYOPHARM THERAPEUTICS, INC.; SANDANAYAKA, Vincent, P.; SHACHAM, Sharon; MCCAULEY, Dilara; SHECHTER, Sharon; WO2013/19548; (2013); A1;,
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Pyrimidine – Wikipedia

Application of 13544-44-0, 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 13544-44-0, name is 2,4-Dichloro-5-iodopyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 2,4-dichloro-5-iodopyrimidine (compound 201) (80.00g, 0.291mol, 1.0eq.) was dissolved in ethanol (800 ml) was added triethylamine (88.18g, 0.873mol, 3.0eq.), and The mixture was then placed in an ice bath with stirring, when the temperature dropped to 0C-5C, dropwise addition of cyclopentylamine (49.50g, 0.582mol, 2.0eq.), addition was complete 30 minutes, and then maintaining the temperature at about 5C with stirring. Monitored by HPLC, 2,4-dichloro-5-iodo-pyrimidine as peak area ratio of less than 1%, the reaction was terminated. The reaction mixture was concentrated after adding ethyl acetate (300mL), water (300mL), extraction and liquid separation. Aqueous phase was extracted with ethyl acetate (200mL×2) and extracted. The combined organic phases, the organic phase was washed with saturated brine (200mL) was extracted, dried over anhydrous sodium sulfate. The organic phase was concentrated in vacuo, the residue was purified by silica gel column chromatography to give compound 2-chloro-N-cyclopentyl-5-iodopyrimidin-4-amine after isolation (87.88g, yield rate: 93.5%).

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 13544-44-0, 2,4-Dichloro-5-iodopyrimidine.

Reference:
Patent; Guangzhou Kaisheng Beite Pharmaceutical Co., Ltd.; Cai, Xiong; Qian, Changgeng; Liu, Bin; Li, Junqi; Lin, Mingsheng; Qing, Yuanhui; Weng, Yunwo; Wang, Yanyan; Xue, Weicai; You, Huajin; Zhou, Shiqing; (67 pag.)CN105622638; (2016); A;,
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