Pyrimidines

Adding a certain compound to certain chemical reactions, such as: 4270-27-3, 6-Chloropyrimidine-2,4(1H,3H)-dione, 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: C4H3ClN2O2, blongs to pyrimidines compound. COA of Formula: C4H3ClN2O2

1-Bromo-2-butyne (9.4 mL, 0.11 mol) was added to a mixture of 6-chloropyrimidine-2,4(1H,3H)-dione (14.6 g, 0.1 mol), ethyldiisopropylamine (15 mL, 0.15 mol) and 250 mL of N,N-dimethylformamide. The reaction mixture was stirred overnight at ambient temperature. For work-up, the reaction mixture was diluted with approximately 300 mL of water. The light precipitate formed was suction filtered and washed with water. The filter cake was washed with diethyl ether and dried to give 1-(but-2-yn-1-yl)-6-chloropyrimidine-2,4(1H,3H)-dione (9) as a yellow powder (17 g, yield 85%). 1H NMR (400 MHz, CDCl3) delta 5.91 (s, 1H), 4.75 (d, J = 2.0 Hz, 2H), 1.82 (t, J = 2.0 Hz, 3H). ESI-MS calculated for (C8H8ClN2O2) [M + H]+, 199.03, found 199.0.

The synthetic route of 4270-27-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xie, Hui; Zeng, Lili; Zeng, Shaogao; Lu, Xin; Zhao, Xin; Zhang, Guicheng; Tu, Zhengchao; Xu, Hongjiang; Yang, Ling; Zhang, Xiquan; Wang, Shanchun; Hu, Wenhui; European Journal of Medicinal Chemistry; vol. 68; (2013); p. 312 – 320;,
Pyrimidine | C4H4N2 – PubChem,
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. 1193-21-1, name is 4,6-Dichloropyrimidine, molecular formula is C4H2Cl2N2, 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. Computed Properties of C4H2Cl2N2

Step 1: 6-chloropyrimidin-4-amine Intermediate 14 4,6-Dichloropyrimidine (7.5 g, 50 mmol) was suspended in ammonium hydroxide (64 mL) in a sealed tube. The tube was sealed and heated at 100 C. in an oil bath overnight. The reaction mixture was cooled to rt. The solid was removed by filtration, washed with water and dried under high vacuum to afford 6-chloropyrimidin-4-amine (5.23 g, 80%) LC-MS (AA) ES+ 130.

With the rapid development of chemical substances, we look forward to future research findings about 1193-21-1.

Reference:
Patent; Millennium Pharmacuticals, Inc.; US2012/15943; (2012); A1;,
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Pyrimidine – Wikipedia

Related Products of 108831-66-9, Adding some certain compound to certain chemical reactions, such as: 108831-66-9, name is 6-Methyl-3H-thieno[2,3-d]pyrimidin-4-one,molecular formula is C7H6N2OS, 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 108831-66-9.

[00127] To a solution of 6-methylthieno [2,3-d]pyrimidin-4(3H)-one (1.0 g, 6.02 mmol) in acetic acid (20 mL) was added bromine (0.46 mL, 18.05 mmol) drop-wise at room temperature. The reaction mixture was stirred at the same temperature for 16 h. After completion of the reaction, the reaction mixture was concentrated, the residue was diluted with saturated sodium bicarbonate solution and extracted with ethyl acetate (3 x 100 mL). The combined organic layer was dried over anhydrous sodium sulphate, filtered and concentrated to get crude product which was purified by silica gel column chromatography using 8% methanol in dichloromethane to afford the title compound 5-bromo-6-methylthieno [2,3-d]pyrimidin- 4(3H)-one(0.54 g, 36.7% yield) as off white solid. [00128] Calculated (M+H): 244.93; Found (M+H): 245.1.

According to the analysis of related databases, 108831-66-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LUC THERAPEUTICS; ANDERSON, David, R.; VOLKMANN, Robert, A.; MENNITI, Frank, S.; FANGER, Christopher; (59 pag.)WO2017/100599; (2017); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 42754-96-1, 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine, 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, 42754-96-1, blongs to pyrimidines compound. Computed Properties of C5H2Cl2N4

This reaction was run five times with 1 g each batch. The amounts shown are a total of each of the five batches.To a solution of 4,6-dichloro-1H-pyrazolo[3,4-d]pyrimidine (compound la) (5 g, 26.5mmol, Chemshuttle) in ACN (100 mL) was added N-bromosuccinimide (5.18 g, 29.1 mmol).The reaction was heated in a microwave at 100 C over 15 minutes. ACN was removed under vacuum. The remaining residue was partitioned between EtOAc (150 mL) and water (300mL H20 + 100 mL NaCI). The aqueous layer was extracted wit EtOAc (150 mL). Organic layers were combined, washed water (100 mL H20 + 20 mL NaCI) X 3, dried over Na2SO4, filteredand evaporated under reduced pressure. The residue was triturated with water (30 mL) x3 and dried in vacuo at 45C to afford a solid 3-bromo-4,6-dichloro-1H-pyrazolo[3,4- d]pyrimidine (compound 1) (6.5 g, 92% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,42754-96-1, its application will become more common.

Reference:
Patent; UNIVERSITY OF DUNDEE; GILBERT, Ian Hugh; THOMAS, Michael George; (37 pag.)WO2016/116752; (2016); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 10320-42-0, 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. 10320-42-0, name is 2-Chloro-5-nitropyrimidine. A new synthetic method of this compound is introduced below.

At room temperature, 2-chloro-5- nitropyrimidine (118 mg, 1 mmol) and benzimidazole (175.5 mg, 1.1 mmol) were dissolved in 15 ml of acetonitrile and the anhydrous potassium (414 mg, 3mmol) was added and reacted at room temperature overnight. The next day, the reaction solution was poured into water and extracted with ethyl acetate (50 * 2). The organic phase was washed twice with saturated NaCl solution, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to give a yellow-black solid, which was used directly in the next step without purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10320-42-0, 2-Chloro-5-nitropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Ancureall Pharmaceutical (Shanghai) Co., Ltd.; SI, Jutong; JIANG, Meifeng; (136 pag.)EP3424924; (2019); A1;,
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Pyrimidine – Wikipedia

Related Products of 131860-97-4, Adding some certain compound to certain chemical reactions, such as: 131860-97-4, name is (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate,molecular formula is C15H13ClN2O4, 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 131860-97-4.

Methyl (£)-2-{2-[6-chloropyiimidin-4-yloxy]phenyl}-3-methoxyacrylate (E) (3g of 95.4% strength) was charged to the reaction tube followed by the solvent (10 ml) then 2- cyanophenol (1.2g), base (1.5 mol equivalents) and the compound being tested as a catalyst (15 mol%). The reaction mixtures were held, with stirring, at 400C for 4hrs, then at 6O0C for 2 hrs. The reaction was monitored for formation of product, throughout the hold period, by Gas Chromatography. Results are recorded as area % levels of methyl (£)-2-{2-[6- chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (II) and methyl (E)-2-{2-[6-(2- cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (I) in the reaction mixture.The following systems were tested:TABLE l The results are shown in Table 2 below:TABLE 2; A stirred solution of (E)-2-{2-[6-chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (80.0g at 98%w/w, 0.24mols) in DMF (80g) was heated to approximately 500C and then potassium carbonate (51.6g at 98%w/w, 0.37mols) was added. The mixture was heated to 6O0C and a solution of 2-cyanophenol in DMF was added (63.9g at 50%w/w, 0.27mols), followed by quinuclidine hydrochloride (1.85g at 97%w/w, 0.012mols). The reaction mixture was heated to 8O0C (exotherm took the temperature to 910C) and held for 20 minutes when analysis indicated that the reaction was complete. The DMF was distilled off under vacuum to a final temperature of 1000C and then toluene (134.8g) was charged, followed by hot water (259.4g), maintaining the temperature of the mixture above 700C. The mixture was stirred at 800C for 30 minutes, settled and then the aqueous phase separated. The toluene phase (233.Og) contained methyl (E)-2-{2-[6-(2-cyanophenoxy)pyrimidm-4-yloxy]phenyl}-3- methoxyacrylate (41.4%w/w) 98.1 % of theory.; stirred solution of (JS)-2-{2-[6-chloropyrimidiri-4-yloxy]phenyl}-3-methoxyacrylate (80.0g at 98%w/w, 0.24mols) in DMF (80g) was heated to approximately 500C and then potassium carbonate (51.6g at 98%w/w, 0.37mols) was added. The mixture was heated to 600C and quinuclidine hydrochloride (1.85g at 97%w/w, 0.012mols) was charged. The mixture was held at 600C for 10 minutes before adding a solution of 2-cyanophenol in DMF (63.9g at 50%w/w, 0.27mols). The mixture was heated to 80C (exotherm took the temperature to 850C) and held for 90 minutes when analysis indicated that the reaction was complete. The DMF was distilled off under vacuum to a final temperature of 100C and then toluene (134.8g) was charged, followed by hot water (259.4g), maintaining the temperature. of the mixture above 70C. The mixture was stirred at 8O0C for 30 minutes, settled and then the aqueous phase separated. The toluene phase (230.6g) contained methyl (E)-2-{2-[6-(2- cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (35.8%w/w) 84.0% of theory.; A stirred solution of (E)-2-{2-[6-chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (80.0g at 98%w/w, 0.24mols) in DMF (80g) was heated to approximately 5O0C and then potassium carbonate (51.6g at 98%w/w, 0.37mols) was added. The mixture was heated to 60C and a solution of 2-cyanophenol in DMF was added (63.9g at 50%w/w, 0.27mols), followed by quinuclidine hydiOchloride (0.37g at 97%w/w, 0.002mols). The reaction mixture was heated to 8O0C (exotherm took the temperature to 890C) and held for 20 minutes when analysis indicated that the reaction was complete. The DMF was distilled off under vacuum to a final temperature of 1000C and then toluene (134.8g) was charged, followed by hot water (259.4g), maintaining the temperature of the mixture above 700C. The mixture was stirred at 800C for 30 minutes, settled and then the aqueous phase separated. The toluene phase (233.Og) contained methyl (E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3- methoxyacrylate (41.3%w/w) 97.9% of theory.; A stirred solution of (E)-I- {2- [6-chloiOpyrimidin-4-yloxy]phenyl} -3 -methoxyacrylate (80.0g at 98%w/w, 0.24mols) in DMF (80g) was heated to approximately 5O0C and then potassium carbonate (51.6g at 98%w/w, 0.37mols) was added. The mixture was heated to 600C and a solution of 2-cyanophenol (32.8g at 97.5%w/w, 0.27mols) in DMF (32g) was added, followed by quinuclidine hydrochloride (0.07g at 97%w/w, 0.0005mols). The reaction mixture was heated to 8O0C (exotherm took the temperature to 85C) and held for 105 minutes when analysis indicated that the reaction was complete. The DMF was distilled off under vacuum to a final temperature of 1000C and then toluene (134.8g) was charged, followed by hot water (259.4g), maintaining the temperature of the mixture above 700C. The mixture was stirred at 8O0C for 30 minutes, settled and then the aqueous phase separated. The toluene phase (229.8g) contained methyl (E)-2-{2-[6-(2-cyanorhohenoxy)pyrimidin-4- yloxy]phenyl}-3-methoxyacrylate (40.5%w/w) 94.7% of theory.; A stirred DMF solution of (E)-2-{2-[6-chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (193.Og at 47.12%w/w, 0.283mols) was heated to …

According to the analysis of related databases, 131860-97-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA LIMITED; WO2008/43977; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 4349-07-9 ,Some common heterocyclic compound, 4349-07-9, molecular formula is C4H3IN2O, 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.

10 g of the compound obtained in step 1) above was added to 60 mL of phosphorus oxychloride and stirred at 110C for 2 hours. After the reaction was completed, the reaction solution was cooled to room temperature and distilled under a reduced pressure to remove solvent therefrom. Toluene was added to the residue, and the resulting residue was concentrated under a reduced pressure to remove the solvent, and this procedure was repeated 3 times. The solid thus obtained was dried under a reduced pressure to obtain the title compound (13 g).1H-NMR (300MHz, DMSO-d6) delta 13.27 bs, 1H), 9.18 (s, 1H), 8.98 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4349-07-9, its application will become more common.

Reference:
Patent; HANMI HOLDINGS CO., LTD.; CHA, Mi Young; KIM, Mi Ra; KANG, Seok Jong; KIM, Se Young; JUNG, Young Hee; LEE, Kwang Ok; SONG, Ji Yeon; KIM, Young Hoon; KIM, Eun Young; KIM, Maeng Sup; WO2011/99764; (2011); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 14080-23-0, name is 2-Cyanopyrimidine, the common compound, a new synthetic route is introduced below. Safety of 2-Cyanopyrimidine

a) 2-Aminomethyl-pyrimidine 66.2 g (0.63 mole) of 2-cyano-pyrimidine (Liebigs Ann. Chem. 1981, 333) in 1.9 1 of ethanol are hydrogenated in the presence of 130 ml of liquid ammonia and 5 g of Pd-C (5% Pd) at 20 C. and 5-10 bar of hydrogen. The catalyst is filtered off, the filtrate is concentrated and the residue is distilled. Yield: 48.8 g (71% of theory) Boiling point: 82 C./4 mbar

The synthetic route of 14080-23-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Aktiengesellschaft; US5312823; (1994); 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. 50270-27-4, name is 2,4,6-Trichloropyrimidine-5-carbaldehyde, molecular formula is C5HCl3N2O, 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. Quality Control of 2,4,6-Trichloropyrimidine-5-carbaldehyde

To a solution of 5-methyl-lH-pyrazol-3-amine (550 mg, 5.67 mmol), DIEA (0.906 mL, 5.2 mmol), and KI (392 mg, 2.36 mmol) in DMF (10 mL) was added 2,4,6-trichloropyrimidine-5-carbaldehyde (1 g, 4.73 mmol). The mixture was stirred at rt for 3 h, then water was added and the mixture was stirred for 20 min at rt. The precipitated solid was collected by filtration to afford 2,4-dichloro-6-(5- methyl-lH-pyrazol-3-ylamino)pyrimidine-5-carbaldehyde (1.4 g) as a yellow solid that was used without further purification. LCMS (ESI) m/z 272 (M + H)+.

With the rapid development of chemical substances, we look forward to future research findings about 50270-27-4.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; CHAO, Qi; HADD, Michael, J.; HOLLADAY, Mark, W.; ROWBOTTOM, Martin; WO2012/30924; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 5466-43-3, 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 5466-43-3 as follows.

General procedure: To the solution of compound 8 (0.23g, 1.2mmol) in THF (5mL) was added DIPEA (1.8mmol) and bicyclic amine or piperidin amine (1.44mmol). The reaction was stirred at r.t. for overnight. Then the mixture was diluted with ethyl acetate, washed with brine, dried over MgSO4, and evaporated. The residue was purified by column chromatography to give the product. 4.1.4 40 tert-butyl 4-((2-chloro-6, 7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)amino)piperidine-1-carboxylate (9)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5466-43-3, its application will become more common.

Reference:
Article; Fang, Yuanying; Xiong, Lijuan; Hu, Jianguo; Zhang, Shaokun; Xie, Saisai; Tu, Liangxing; Wan, Yang; Jin, Yi; Li, Xiang; Hu, Shaojie; Yang, Zunhua; Bioorganic Chemistry; vol. 86; (2019); p. 103 – 111;,
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Pyrimidine – Wikipedia