Pyrimidines

Related Products of 32779-36-5, 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. 32779-36-5, name is 5-Bromo-2-chloropyrimidine, molecular formula is C4H2BrClN2, 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.

Step 1 : 1-(5-Bromo-2-pyrimidinyl)-4-piperidinol (16)A round-bottomed flask was charged, under N2, with 4-hydroxypiperidine (1.93 g, 10 mmol), diisopropylethylamine (5.22 ml_, 30 mmol), 5-bromo-2-chloropyrimidine (1.01 g, 10 mmol), and acetonitrile (50 ml_). The mixture was refluxed for 15 h and then concentrated under reduced pressure. The crude product was redissolved in CH2CI2 (150 ml), washed with H2O (2 x 20 ml_), brine (1 x 20 ml_), dried over Na2SO4, and filtered. The filtrate was concentrated under reduced pressure and the crude material was purified by flash SiO2 column chromatography to afford 2.55 g (99percent) of the title compound 16 as a white solid. 1H NMR (400 MHz, DMSO-d6): delta 8.34 (s, 2 H), 4.73 (d, J = 4.0 Hz, 1 H), 4.17 – 4.12 (m, 2 H), 3.74 – 3.68 (m, 1 H), 3.28 – 3.22 (m, 2 H), 1.76 – 1.70 (m, 2 H), 1.33 – 1.25 (m, 2 H); LCMS (ESI): m/z 260 (M + H)+.

According to the analysis of related databases, 32779-36-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/8895; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1193-24-4, 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. 1193-24-4, name is 4,6-Dihydroxypyrimidine. A new synthetic method of this compound is introduced below.

One-step process for preparing 4, 6 – dichloro pyrimidine synthesis process, the synthesis process comprises the following steps: (1) input to the tower in the reactor 1 parts by weight of 4, 6 – dihydroxy pyrimidine and 3 parts by weight of chloroform, opening the stirrer stirring, continue adding 0.5 parts by weight of pyridine catalyst, and then open the jacket steam make the tower the temperature in the reactor is increased to 50 C, from the tower bottom of the reactor 1 parts by weight of phosgene, phosgene first of all through the reactor internal gas distributor, the gas distributor is triangle shape is placed in the bottom of the tower type reactor, gas distributor there are a lot of small holes is uniform and compact, phosgene is too high and the tower type reactor internal, then react with the material; (2) after the reaction, the bottom of the tower type reactor by nitrogen catches up with was mad, mixing the gas via the gas outlet of the tower the top of the reactor, into the collecting tank, the upper part of the collecting tank is provided with a ammonia-water spray system, the bottom of the traps the pot installed with a fan, when the gas enters into the collecting tank, by the fan gas into the ammonia-water spray system, so as to avoid the leakage of phosgene and hydrogen chloride gas; then the tower in the reactor in product transfer to the rectifying tower, are respectively arranged successively rectification temperature is 55 – 70 C, 105 – 125 C and 170 – 180 C, respectively collecting the corresponding temperature of the fraction, can be recycled chloroform solvent and pyridine catalyst, to a temperature of 170 – 180 C fraction is washed by water after cooling, drying, to obtain the 4, 6 – dichloro pyrimidine.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1193-24-4, its application will become more common.

Reference:
Patent; Anhui Guangxin Agrochemical Co., Ltd; Huang, Jinxiang; Guo, Xuejun; Wu, Jianping; Hu, Minghong; Tang, Xiude; Cheng, Weijia; Li, Hongwei; Xu, Xiaobing; Gao, Yanbing; (4 pag.)CN106045917; (2016); A;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 5177-27-5, 5-Amino-2,4-dichloropyrimidine, 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 5-Amino-2,4-dichloropyrimidine, blongs to pyrimidines compound. Application In Synthesis of 5-Amino-2,4-dichloropyrimidine

To a stirring suspension of 2,4-Dichloro-pyrimidin-5-ylamine (3.03 g, 18.1 mmol) in n- BuOH (40 mL) is added (lS,2S)-2-Amino-cyclopentanol hydrochloride (2.50 g, 17.2 mmol) and DIEA (9.20 ml, 51.8 mmol). The mixture is stirred at 130 C for 4 h. The reaction mixture is then concentrated under reduced pressure and the crude product is triturated to a solid in EtOAc and heptane and filtered to yield BT-1.

The synthetic route of 5177-27-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BAKONYI, Johanna; BRUNETTE, Steven Richard; COLLIN, Delphine; HUGHES, Robert Owen; LI, Xiang; LIANG, Shuang; SIBLEY, Robert; TURNER, Michael Robert; WU, Lifen; ZHANG, Qiang; WO2015/160654; (2015); A1;,
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Pyrimidine – Wikipedia

Related Products of 1060816-58-1, 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 1060816-58-1, name is 5-Bromo-2-chloro-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

tert-Butyl trans-A-((5 -bromo-2-(butylamino)- 7H-pyrrolo[2,3-d]pyrimidin-7-yl methyl)cyclohexylcarbamate A 10 mL microwave tube was charged with 5-bromo-2-chloro-7H-pyrrolo[2,3-d]pyrimidine (0.23 g, 1.0 mmol), tert-butyl trans-4-(iodomethyl)cyclohexylcarbamate (0.51 g, 1.5 mmol), K2CO3 (0.28 g, 2.0 mmol), DMSO (1.5 mL) and THF (3 mL). The mixture was heated at 150 C for 100 min in microwave. After the reaction mixture was cooled to ambient temperature, n-butylamine ( 0.18 g, 2.5 mmol) was added. The mixture was heated at 150 C for 90 min in microwave. After cooling to ambient temperature, the reaction was poured into water and extracted with EtOAc (3X). The combined organic layer was dried (Na2SO4) and concentrated. The crude mixture was purified by Isco to provide tert-butyl trans-4-((5-bromo-2-(butylamino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl)cyclohexylcarbamate (0.35 g, 73%) as a white solid. MS m/z 480.2 [M+H

According to the analysis of related databases, 1060816-58-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; WANG, Xiaodong; LIU, Jing; YANG, Chao; ZHANG, Weihe; FRYE, Stephen; KIREEV, Dmitri; WO2013/52417; (2013); A1;,
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Synthetic Route of 13223-25-1, 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.13223-25-1, name is 2-Chloro-4,6-dimethoxypyrimidine, molecular formula is C6H7ClN2O2, molecular weight is 174.59, as common compound, the synthetic route is as follows.

Example 7; Preparation of 2-hydroxymethyl-8-(4,6-dimethoxy-pyrimidin-2-yl)-l ,4-dioxa-8- azaspiro[4,5]decane (starting material for the preparation of Compound-7); 25 g of piperdone hydrochloride was slowly added in lots to 2g of TBAB and 67g of K2CO3 in 250 ml of acetonitrile at 50-60 (provide exact value), then 25 g of piperdone hydrochloride was slowly added in lots and the reaction mixture stirred for I hr. 29 g of 4,6-dimethoxy-2- chloropyrimidine was added slowly over a period of I hr and the reaction mixture was refluxed for 1 1 hours at 600C.The reaction mixture was neutralized with aq.NaOH solution and extracted with MDC, (methylene dichloride). Organic layer was distilled off to get l -(4-6-dimcthoy- pyrimidin-2-yl)-piperidin-4-one.45g of l -(4-6-dimethoxy-pyrimidin-2-yl)-piperidin-4-one. and 5.2 g of PTSA were stirred in toluene (400 ml) for half an hour. 21 g Glycerol ( 1.2 mole) was added drop wise and the reaction mixture was refluxed at 120 C for 7 hours. Toluene was removed to get the desired product with 85% yield.

The chemical industry reduces the impact on the environment during synthesis 13223-25-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; COUNCIL OF SCIENTIFIC &; INDUSTRIAL RESEARCH; DESHPANDE, Mukund, Vinayak; DESHPANDE, Sunita, Ranjan; SHIRAZI, Fazal; CHAUDHARY, Preeti, Madhukar; RAO, Nelavelli, Malleswara; MOHANTY, Baidyanath; SHARMA, Nageshwar, Nath; BACHHAWAT, Anand, Kumar; KALIANNAN, Ganesan; PAUL, Sanjoy; KUMAR, Raj; RAO, Bommena, Vittal; GAWALI, Bhimrao, Bodhanrao; REDDY, Vaddu, Venkata, Narayana; YADAV, Jhillu, Singh; WO2010/109299; (2010); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.1753-50-0, name is 2-Chloropyrimidine-5-carbonitrile, molecular formula is C5H2ClN3, molecular weight is 139.54, as common compound, the synthetic route is as follows.Quality Control of 2-Chloropyrimidine-5-carbonitrile

To a stirred solution of compound GV (0.5 g, 1.78 mmol) and 2-chloropyrimidine-5-carbonitrile (AF, 0.37 g, 2.67 mmol) in EtOH (20 mL) was added DIPEA (0.96 mL, 5.35 mmol) and the reaction mixture was stirred at 90C for 14 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using 2% MeOH/DCM to afford compound GW (0.35 g, 51.0%) as an off white solid. 1H NMR (400 MHz, DMSO-d6): _ 8.80 (d, = 8.4 Hz , 1H), 8.69 (s, 2H), 7.46 – 7.39 (m, 2H), 7.38-7.14 (m, 4H), 5.23-5.18 (m, 1H), 3.41-3.37 (m, 1H), 3.30-3.25 (m, 1H), 2.83 (s, 3H); LC-MS: m/z 384.05 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1753-50-0, 2-Chloropyrimidine-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; VPS-3, INC.; YATES, Christopher, M.; (397 pag.)WO2018/165520; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 3177-24-0, 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. 3177-24-0, name is 2,4-Dichloropyrimidine-5-carbonitrile, molecular formula is C5HCl2N3, 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.

General procedure: DIPEA (0.86mmol) was added to the solution of 2,4-dichloropyrimidine-5-carnonitrile (0.57mmol) in DMF (0.5ml) and stirred at room temperature for 10min. A solution of aminobenzene reagent corresponding to desired product (0.57mmol) in DMF (0.5ml) was added dropwise to the reaction mixture and stirred for 1h. The resultant was evaporated under vacuum and extracted with EtOAc. The organic layer was collected, washed with brine, dried over MgSO4, filtered, and dried under reduced pressure. 4c was obtained from the reaction of 4b, whereby substitution at the 2-position occurred.

According to the analysis of related databases, 3177-24-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Phuangsawai, Oraphan; Beswick, Paul; Ratanabunyong, Siriluk; Tabtimmai, Lueacha; Suphakun, Praphasri; Obounchoey, Phongphat; Srisook, Pimonwan; Horata, Natharinee; Chuckowree, Irina; Hannongbua, Supa; Ward, Simon E.; Choowongkomon, Kiattawee; Gleeson, M. Paul; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 896 – 905;,
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Pyrimidine – Wikipedia

Electric Literature of 56-09-7, 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. 56-09-7, name is 2-Amino-6-hydroxypyrimidin-4(3H)-one. A new synthetic method of this compound is introduced below.

Phosphorus oxychloride (58.7mL, 630mmol) was added to a 500mL single-necked round bottom flask, N, N-dimethylformamide (12.1mL, 157mmol) was added dropwise at a low temperature bath of 5 C, and then transferred to 25 C , 2-Amino-4,6-dihydroxypyrimidine (10g, 78.7mmol) was added in portions, and the temperature was raised to 100 C to react for 5 hours. The reaction was stopped, most of the phosphorus oxychloride was removed by rotary evaporation under reduced pressure, water (900 mL) was added, and the mixture was stirred at 25 C for 32 hours, filtered, and the resulting solid was added to ethyl acetate (50 mL). After stirring for 30 minutes, Filter and dry the filter cake to give the title compound as a yellow solid (12.2 g, 80.8%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,56-09-7, 2-Amino-6-hydroxypyrimidin-4(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Shenzhen Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Zhong Wenhe; Deng Kang; (40 pag.)CN111072675; (2020); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 3438-46-8 ,Some common heterocyclic compound, 3438-46-8, molecular formula is C5H6N2, 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.

Step A-Preparation of pyrimidine-4-yl formaldehyde Pyrimidine-4-yl formaldehyde was prepared from 4-methyl pyrimidine through a reference described in M. C. Liu et al., J Med Chem., 1995, 38 (21), 4234-4243.

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. 3438-46-8, 4-Methylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Amgen Inc.; US6878714; (2005); B2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 761440-16-8, name is 2,5-Dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C13H13Cl2N3O2S

2,5-dichloro-N-(2-(isopropylsulfonyl)phenyl)py-rimidine-4-amine (472 mg, i.36 mmol) was dissolved in0.08 M HC1-ethoxyethanol (i .0 mE), to which the compound (200 mg, i . i3 mmol) prepared in preparative example 20 was added, followed by stirring at 80 C. for i2 hours. The reaction mixture was cooled to room temperature, neutralized with sodium hydrogen carbonate aqueous solution, and extracted twice with ethylacetate. The extracted organic layer was dried over sodium sulfate and then filtered. The solvent was eliminated by distillation under reduced pressure. Then, purification was performed by silica gel colunm chromatography (eluent: methanol/ dichioromethane, i/9) to give the target compound 2-(4-((5- chioro-4-((2-(isopropylsulfonyl)phenyl)amino)pyrimidine- 2-yl)amino)-5-methoxy-2-methylphenyl)acetonitrile as a white solid (450 mg, 0.926 mmol, yield: 8i%).10581] ?H-NMR (300 MHz, CDC13) oe 9.53 (s, br, iH),8.53 (d, J=8.3 Hz, iH), 8.i8 (s, iH), 8.i3 (s, iH), 7.94 (d, J=7.9 Hz, iH), 7.64 (t, J=8.4 Hz, iH), 7.55 (s, br, iH), 7.28 (t, J=7.8 Hz, iH), 6.86 (s, iH), 3.9i (s, 3H), 3.63 (s, 2H), 3.26 (sept, J=6.9 Hz, iH), 2.i7 (s, 3H), i.3i (d, J=6.9 Hz, 6H); EC/MS 485.9 [M+H].

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, 761440-16-8, 2,5-Dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; Kim, Pilho; Kim, Hyoung Rae; Cho, Sung Yun; Ha, Jae Du; Jung, Hee Jung; Yun, Chang Soo; Hwang, Jong Yeon; Park, Chi Hoon; Lee, Chong Ock; Ahn, Sunjoo; Chae, Chong Hak; (97 pag.)US2018/111905; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia