Pyrimidines

Reference of 24391-41-1 ,Some common heterocyclic compound, 24391-41-1, molecular formula is C7H3ClN4, 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.

Synthesis of Compound 16.5. A solution of compound 16.4 (600 mg, 3.4 mol), DIPEA (0.8 ml, 4.4 mmol), and Pd(dppf)2Cl2 (27 mg, 0.04 mmol) in MeOH (12 ml) under CO (100 psi) was heated (100 C.) for 16 hr. The solvent was removed in vacuo, and the residue was triturated (EtOAc) to afford compound 16.5 (400 mg, 58%) as an off-white solid. 1H-NMR (500 MHz, DMSO-d6) delta 13.64 (bs, 1H), 9.06(s, 1H), 8.80 (s, 1H), 3.98 (s, 3H). MS m/z 203 [M+1]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,24391-41-1, its application will become more common.

Reference:
Patent; Sunesis Pharmaceuticals, Inc; US2009/5359; (2009); A1;,
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Synthetic Route of 1004-40-6 , The common heterocyclic compound, 1004-40-6, name is 6-Amino-4-hydroxy-2-mercaptopyrimidine, molecular formula is C4H5N3OS, 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.

Representative procedure for the synthesis of dihydropyrido[2,3-d]pyrimidines 4: N,N-Dimethyl-6-aminouracil 1a (0.310 g, 2 mmol benzaldehyde 2a (0.212 g, 2 mmol), 3-cyanoacetyl indole 3 (0.368 g, 2 mmol) were taken in a round bottom flask containing ethanol (10 mL). To this was added InCl3 (5 mol %) and the reaction mixture was refluxed for 6 h. After completion of the reaction (monitored by TLC), the reaction mixture was cooled and filtered. The solid product obtained was washed with water and ethanol, and finally recrystallized from ethanol. The structure of the compound was ascertained as 4a from the spectroscopic data and elemental analysis. Yield = 0.670 g (82%) Compound 4a: Similarly compounds 4b-q were synthesized and characterized.

The synthetic route of 1004-40-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Seetham Naidu; Borah, Pallabi; Bhuyan, Pulak J.; Tetrahedron Letters; vol. 53; 31; (2012); p. 4015 – 4017;,
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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. 22536-64-7, name is 2-Chloro-4-methoxy-6-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C6H7ClN2O

A mixture of tert-butyl 4-(4-hydroxyphenyl)piperazine- 1 -carboxylate (2.78 g, 10.0 mmol), 2-chloro-4-methoxy-6-methylpyrimidine (1.74 g, 11.0 mmol) and sodium carbonate (1.16 g, 11.0 mmol) in acetonitrile (10 mL) was heated to 80C and stirred for 20 hours under an N2 atmosphere. The reaction mixture was then cooled to rt. The resulting mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 10/1) to give the title compound as a white solid (1.02 g, 25.5%). The compound was characterized by the following spectroscopic data:LC-MS (ESI, pos. ion) m/z: 401.2 [M + H] and?HNMR(400 MHz, CDC13) (ppm): 7.13 -7.11 (m, 2H), 6.96-6.92 (m, 2H), 6.27 (s, 1H), 3.84(s, 3H), 3.59 (t, J 4.8 Hz, 4H), 3.11 (t, J= 4.7 Hz, 4H), 2.33 (s, 3H), 1.48 (s, 9H).

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, 22536-64-7, 2-Chloro-4-methoxy-6-methylpyrimidine.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; JIN, Chuanfei; CHENG, Changchung; WO2015/169180; (2015); A1;,
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Synthetic Route of 51-20-7, 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.51-20-7, name is 5-Bromouracil, molecular formula is C4H3BrN2O2, molecular weight is 190.9828, as common compound, the synthetic route is as follows.

5-bromouracil (191 g, 99.5% content; ie 1 mol),Tributylphosphine oxide (111.2 g, 98% content; ie 0.5 mol) andNitrile(200 ml) charged into 1000 ml with thermometer, stirring, constant pressure funnel,In a three-necked flask of a condenser (-5 – 10 C), the system was purged with nitrogen to check for leaks.The mixture of 5-bromouracil is heated to 80 C, solid phosgene (320 g, 99% content;That is, 3.2 mol) and 400 ml of a nitrile solution were added dropwise to the reaction solution through a constant pressure funnel.A small amount of phosgene begins to reflux during the addition. The phosgene was added for 70 minutes.The mixture was heated to 125 C. When the temperature is 90 C, a large amount of gas is released while the phosgene of the condenser is largely refluxed. After 40 minutes, the reaction mixture was a clear red color.The deflation rate after 40 minutes was very slow; the reaction solution was sampled and then the reaction was continued for 1 hour, during which time all deflation had stopped. HPLC analysis indicated complete reaction. The reaction mixture was cooled and unreacted phosgene was removed by purging with nitrogen. The column was packed, the solvent was recovered under reduced pressure, and the product was further distilled to obtain 204.5 g of a product of 99% or more, and the yield was about 89.7%.

The chemical industry reduces the impact on the environment during synthesis 51-20-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Hangzhou Bulang Bio-pharmaceutical Technology Co., Ltd.; Huang Guoxiang; Ma Xiaoke; (6 pag.)CN109516958; (2019); A;,
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Reference of 36082-50-5 ,Some common heterocyclic compound, 36082-50-5, molecular formula is C4HBrCl2N2, 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.

Preparation of 5-Bromo-2-chloro-4-methylsulfanyl-pyrimidine 2 g of MeSNa (28.5 mmol; 1 eq.) and 6.5 g of 5-bromo-2,4-dichloropyrimidine (28.5 mmol, 1 eq.) were stirred in 50 mL dry acetonitrile at rt for 24 h. Then the mixture was poured into water, extracted with DCM, dried (Na2SO4) and evaporated to dryness. The product was recrystallized from hexane to yield 4 g of Intermediate 10 (70 % yield). 1H-NMR (400 MHz, CDCl3): 8.31 (s, 1 H); 2.59 (s, 3 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. 36082-50-5, 5-Bromo-2,4-dichloropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer Schering Pharma Aktiengesellschaft; EP1878726; (2008); A1;,
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Reference of 5177-27-5, 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.5177-27-5, name is 5-Amino-2,4-dichloropyrimidine, molecular formula is C4H3Cl2N3, molecular weight is 163.9927, as common compound, the synthetic route is as follows.

5-amino-2,4-dichloropyrimidine (0.15 mol) was dissolved in anhydrous tetrahydrofuran (100 mL),Add triethylamine (30.4g, 0.3mol) dropwise to the reaction system with a constant pressure dropping funnel with stirring at room temperature.The mixed solution with tert-butylamine (21.9g, 0.3mol) was dripped, and the reaction system was transferred to a 100 C oil bath for 16h.TLC showed the reaction was complete. After cooling to room temperature, water (100 mL) was added.Extract with ethyl acetate (100 mL x 3) and combine the organic phases.The organic phase was washed with saturated sodium chloride water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.It was separated and purified by silica gel column chromatography to obtain a red-brown solid (21.0 g, yield 69.8%).

Statistics shows that 5177-27-5 is playing an increasingly important role. we look forward to future research findings about 5-Amino-2,4-dichloropyrimidine.

Reference:
Patent; Jiangnan University; Tang Chunlei; Zhang Qing; Hu Xiaoxia; Zhao Hui; Zhao Kuantao; Zhang Yue; Fan Weizheng; (16 pag.)CN110357885; (2019); A;,
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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. 111196-81-7, name is 2-Chloro-5-ethylpyrimidine. A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Chloro-5-ethylpyrimidine

<142> Preparation Example l:Synthesis of l-(5-methyl-pyrimidin-2-yl )- din-4- l<144> Under a nitrogen atmosphere, in a 500ml flask, 9.6g of 4- hydroxypiper idine and 250ml of 2:1 acetonitr i le/dist i 1 led water-solution were placed, stirred and dissolved. Then, 19.5ml of di isopropylethylamine and 11.2g of 2-chloro-5-ethylpyr imidine were added thereto, followed by heating and reflux for 2.5 days or more. The temperature was lowered to a room temperature, and the resultant product was dissolved in 200ml of IN HC1 aqueous solution, and washed with 200ml of ethyl acetate. The aqueous layer was adjusted to pH 7 by using IN NaOH aqueous solution, and was extracted with 200mL of ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate and vacuum-dried so as to provide a target compound. H NMR (400MHz, CDC13): 8.18(2H, s), 4.37-4,48(2H, m), 3.91-4.0K 1H, m) ,3.22-3.3K2H, m), 2.42-2.5K2H, m) , 1.49-1.99(4H, m) , 1.17-1.2K3H, 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, 111196-81-7, 2-Chloro-5-ethylpyrimidine.

Reference:
Patent; HYUNDAI PHARM CO., LTD.; PARK, Yong Kyu; BANG, Sung Hun; KIM, Jin Woong; LEE, Han Kyu; KIM, Jae Hyun; SON, Chang Mo; LEE, Jun Hee; SHIN, Chang Yong; LEE, Jong Chan; RHEE, Jae Keol; WO2012/11707; (2012); A2;,
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Reference of 171178-33-9, 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 171178-33-9, name is 6-Chloropyrido[3,2-d]pyrimidin-4(3H)-one. This compound has unique chemical properties. The synthetic route is as follows.

6-Chloro-3/7-pyrido[3,2-i/]pyrimidin-4-onc (1.242 g, 6.67 mmol), tert- butyl l-oxa-6- azaspiro[2.5]octane-6-carboxylate (2.34 g, 11 mmol) and K2CO3 (2.76 g, 19.9 mmol) were stirred in DMF (20 ml) at 70 C for 48 hours. The reaction mixture was filtered, and the resulted filtrate was purified by preparative LC (on C-18 Gemini-NX 5 pm column, 5 mM aqueous NH4HC03-MeCN, gradient), to give tert- butyl 4-[(6-chloro-4-oxo-quinazolin-3- yl)methyl]-4-hydroxy-piperidine- 1 -carboxylate.

According to the analysis of related databases, 171178-33-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LES LABORATOIRES SERVIER; VERNALIS (R&D) LIMITED; KOTSCHY, Andras; WEBER, Csaba; VASAS, Attila; KISS, Arpad; MOLNAR, Balazs; STROFEK, Agnes; KUN, Vilibald; MURRAY, James Brooke; MACIAS, Alba; LEWKOWICZ, Elodie; CHANRION, Maia; IVANSCHITZ, Lisa; GENESTE, Olivier; (86 pag.)WO2019/105963; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 696-07-1, 5-Iodouracil, 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, HPLC of Formula: C4H3IN2O2, blongs to pyrimidines compound. HPLC of Formula: C4H3IN2O2

General procedure: In a typical experiment Pd(OAc)2, triphenylphosphine, iodouracil derivatives (1, 5), amine nucleophiles (a-g) and triethylamine were used in the same amount as above and were dissolved in 10mL of DMF under argon in a 100mL autoclave. The atmosphere was changed to carbon dioxide and the autoclave was pressurized to the given pressure with carbon monoxide. (Caution: High pressure carbon monoxide should only be used with adequate ventilation (hood) using CO sensors as well.) The reaction was conducted for the given reaction time upon stirring at 50C. After the given reaction time the reaction mixture was cooled to room temperature and the autoclave was carefully depressurized in a well-ventilated hood. The product mixture was analysed by GC and GC-MS. The work-up of the reaction mixture was identical to that discussed for the atmospheric experiments. 3.4.1 5-(N-tert-Butylglyoxylamido)uracil (3a) Yield: 175mg (73%), Off white powder, m.p. 270-271C; Rf (15% MeOH/CHCl3) 0.65. deltaH (500MHz, DMSO-d6) 11.82 (1H, br s, NH), 11.42 (1H, br s, NH), 8.20 (1H, s, NHCH), 7.98 (1H, s, CONH), 1.31 (9H, 3 x (CH)3). deltaC NMR (125.7MHz) 186.6, 165.7, 161.3, 150.9, 150.6, 108.8, 51.1, 28.7. IR (KBr, nu (cm-1)): 3375 (NH), 1734, 1700, 1669 (CO), 1653 (Amide I.), 1616 (C=C), 1499 (Amide II.); MS m/z (rel. int.): 238 (100, [M-H]-), MS/MS (rel. int.) 238 (19), 223 (10), 195 (32), 123 (8), 111 (100).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,696-07-1, 5-Iodouracil, and friends who are interested can also refer to it.

Reference:
Article; Kollar, Laszlo; Varga, Marta Georgina; Doernyei, Agnes; Takacs, Attila; Tetrahedron; vol. 75; 33; (2019); p. 4632 – 4639;,
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Synthetic Route of 22177-99-7, 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. 22177-99-7, name is 4-(6-Chloro-2-methylpyrimidin-4-yl)morpholine, molecular formula is C9H12ClN3O, 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.

(2-Methyl-6-morpholin-4-yl-pyrimidin-4-yl)-hydrazine A mixture of hydrazine monohydrate (150 ml, 3.09 mmol) and 4-(6-chloro-2-methyl-pyrimidin-4-yl)-morpholine (300 mg, 1.40 mmol) in EtOH (3 ml) was heated under reflux overnight. Additional hydrazine monohydrate (200 ml, 4.20 mmol) was added and the reaction was heated under reflux for a further 24 h. The reaction was allowed to cool to room temperature. The resulting precipitate was collected by filtration to give the title compound (246 mg, 84% yield).

According to the analysis of related databases, 22177-99-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VIFOR (INTERNATIONAL) AG; US2012/202806; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia