Pyrimidines

Electric Literature of 148550-51-0 ,Some common heterocyclic compound, 148550-51-0, molecular formula is C8H10N2O4S, 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.

General procedure: 60percent Sodium hydride (w/w) in mineral oil (0.0015 mol) was added to a mixture of appropriate III (0.001 mol) in THF (15 ml) under the condition of inert atmosphere using N2 flow at 5°C. The reaction mixture was kept for 1 h at room temperature. A solution of 2-(methylsulfonyl)-5-pyrimidinecarboxylic acid, ethyl ester (0.0015 mol) in THF (15 ml) was slowly added to reaction mixture. The resulting reaction mixture was stirred for 2-3 h at 5°C. The distilled water (20 ml) was added. The reaction mixture was extracted (10 ml x 3) with dichloromethane. The separated organic layer was dried over MgSO4, filtered, and the solvent was evaporated under reduced pressure to obtain crude product, recrytallized by ethyl acetate.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,148550-51-0, its application will become more common.

Reference:
Article; Rajak, Harish; Agarawal, Avantika; Parmar, Poonam; Thakur, Bhupendra Singh; Veerasamy, Ravichandran; Sharma, Prabodh Chander; Kharya, Murli Dhar; Bioorganic and Medicinal Chemistry Letters; vol. 21; 19; (2011); p. 5735 – 5738;,
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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. 50270-27-4, name is 2,4,6-Trichloropyrimidine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 2,4,6-Trichloropyrimidine-5-carbaldehyde

To a solution of 2,4,6-trichloro-pyrimidine-5-carbaldehyde (3.7 g, 17.5 mmol) in EtOH (50 mL) cooled to -78 C. was added methyl hydrazine (0.93 mL, 17.5 mmol) and TEA (8 mL). The mixture was stirred for 30 minutes at -78 C then 2 hr at 0 C. The solution was concentrated in vacuo without heating. To the reduced volume solution was added EtOAc and the solution washed with a sat NaHCO3 solution and concentrated in vacuo without heating. Filtration over a small silica gel plug (2:1 EtOAc:Hex) and concentration afforded the desired product as a yellow solid. It should be noted that the reaction with aromatic hydrazine compounds can be conducted at 0 C.

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, 50270-27-4, 2,4,6-Trichloropyrimidine-5-carbaldehyde.

Reference:
Patent; Wyeth; US2009/98086; (2009); A1;,
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Related Products of 1514-96-1 , The common heterocyclic compound, 1514-96-1, name is 4-Chloro-2-(trifluoromethyl)pyrimidine, molecular formula is C5H2ClF3N2, 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.

A mixture of 4-chloro-2-(trifluoromethyl)pyrimidine (0.06 g, 0.329 mmol), 2- (3-fluoro-4-methoxyphenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (0.099 g, 0.394 mmol), CS2CO3 (0.214 g, 0.657 mmol), and KBr (0.039 g, 0.329 mmol) in 1,4- dioxane (1.8 mL) was purged with nitrogen for 15 minutes. PdCl2(dppf)-CH2Cl2 adduct (0.027 g, 0.033 mmol) was added and the mixture purged for a further 5 min. The reaction mixture was heated at 80 C for 1.3 h. the reaction mixture was cool to room temperature and diluted with THF (20 mL) then filtered through diatomaceous earth (Celite). The bed was washed with excess THF. The filtrate was concentrated under reduced pressure. The residue was purified via silica gel chromatography (ethyl acetate and pet ether) to afford 4-(3-fluoro-4-methoxyphenyl)-2- (trifluoromethyl)pyrimidine (0.115 g, 0.275 mmol, 53% yield) as a colorless semisolid. LCMS (ESI) m/e 273.0 [(M+H)+, calcd for C12H9F4N2O, 273.05]; LC/MS retention time (method B); fa = 0.98 min.

The synthetic route of 1514-96-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (485 pag.)WO2017/59085; (2017); A1;,
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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.932-52-5, name is 5-Aminopyrimidine-2,4(1H,3H)-dione, molecular formula is C4H5N3O2, molecular weight is 127.1014, as common compound, the synthetic route is as follows.COA of Formula: C4H5N3O2

Intermediate 4: 6-Methylpyridor3,2-c/lpyrirnidine-2,4(1H,3H)-dione; A mixture of 5-aminouracil (3 g; 23.6 mmol; 1 eq.) and crotonaldehyde (2.04 ml 24.8 mmol; 1.05 eq.) in 20% HCI (20 ml.) was stirred at 1 100C for 1 hour. The solution was evaporated in vacuo and the residue precipitated from EtOH to afford the title compound as a black solid. 1H NMR (300 MHz, DMSO-d6) delta 8.90-8.50 (m, 2H), 7.80 (d, 1 H), 7.51 (d, 1 H), 2.50 (s, 3H). MS (ES+): 178.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,932-52-5, 5-Aminopyrimidine-2,4(1H,3H)-dione, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SERONO S.A.; POMEL, Vincent; GAILLARD, Pascale; DESFORGES, Gwenaelle; QUATTROPANI, Anna; MONTAGNE, Cyril; WO2010/37765; (2010); A2;,
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Application of 90905-33-2, 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.90905-33-2, name is 2-Methylpyrimidine-5-carbaldehyde, molecular formula is C6H6N2O, molecular weight is 122.1246, as common compound, the synthetic route is as follows.

To a mixture of 2-methylpyrimidine-5-carbaldehyde (1.0 g, 8.2 mmol) and triisopropoxymethane (2.3 g, 12 mmol) in isopropanol (15 ml) was added methanesulfonic acid (0.079 g, 0.053 ml, 0.819 mmol). The reaction was stirred at room temperature for 23 hours. Potassium carbonate (1.132 g, 8.19 mmol) was added and the mixture was filtered and the solution was concentrated in vacuo. The crude mixture was purified by flash chromatography to yield 5-(diisopropoxymethyl)-2-methylpyrimidine (536 mg, 29percent) [0357] 1H NMR (500 MHz, CDCl3) delta 8.71 (s, 2H), 5.60 (s, 1H), 3.93 (dt, J=12.3, 6.1 Hz, 2H), 2.74 (s, 3H), 1.21 (dd, J=14.8, 6.1 Hz, 12H)

The chemical industry reduces the impact on the environment during synthesis 90905-33-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; H. Lundbeck A/S; Kilburn, John Paul; Rasmussen, Lars Kyhn; Jessing, Mikkel; Eldemenky, Eman Mohammed; Chen, Bin; Jiang, Yu; Hopper, Allen T.; US2014/107340; (2014); A1;,
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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. 1445-39-2, name is 2-Amino-5-iodopyrimidine. A new synthetic method of this compound is introduced below., Safety of 2-Amino-5-iodopyrimidine

5-(4-(trifluoromethyl)phenyl)pyrazin-2-amine A 100 mL round bottom flask was charged with 2-amino-5-iodopyrimidine (3.66 g, 21.1 mmol), (4-(trifluoromethyl)phenyl)boronic acid (4.00 g, 21.1 mmol) and MeCN (84 mL). Stirred 15 minutes at room temperature until a nice clear solution is obtained. The resulting solution is then treated with 1,1′-Bis(diphenylphosphino)ferrocene-palladium(11)dichloride dichloromethane complex (508 mg, 695 mumol) was added followed by the sodium carbonate 1M aq. (52.7 mL, 52.7 mmol). Reaction refluxed for 2 hours. Reaction cooled down to room temperature and dissolved with ammonium chloride solution (aq. sat.). Aqueous layer extracted with ethyl acetate (3*). Combined organic layers washed with brine (1*), dried over sodium sulfate, filtered and concentrated to give the crude material. Purification by silica gel flash chromatography (Ethyl Acetate/DCM) provide the title compound as a light yellow solid (4.4 g, 87%). 1H NMR (400 MHz, DMSO-d6) delta 6.76 (s, 2H) 7.76 (d, J=8.41 Hz, 2H) 7.99 (d, J=1.57 Hz, 1H) 8.14 (d, J=8.22 Hz, 2H) 8.62 (d, J=1.37 Hz, 1H). MS (M+1): 240.2.

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, 1445-39-2, 2-Amino-5-iodopyrimidine.

Reference:
Patent; Pfizer Inc.; US2012/165343; (2012); A1;,
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Pyrimidine – Wikipedia

Application of 3438-46-8 , The common heterocyclic compound, 3438-46-8, name is 4-Methylpyrimidine, 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.

a- Synthesis of Int. 314: In a dry flask and under N2 atmosphere, a sol. of Ethyl 4-(4- methoxybenzyloxy)benzoate (2.00 g, 6.99 mmol) and 4-methylpyrimidine (723 mg, 7.68 mmol) in dry THF (10 mL) was cooled to 0C and treated with LiHMDS (14.0 mL, 14.0 mmol) (slow addition over 10 min). After the end of the addition, the r.m. was allowed to warm to r.t. and stirred for 17 h. The r.m. was then poured in a 10% aq. sol. of NH4C1 (100 mL). The mixture was filtered on a glass frit. The precipitate was washed with water (2 x 50 mL) and with Et20 (2x 50 mL). The solid was dissolved in a mixture of DCM and MeOH. The organic sol. was dried over MgS04 and evaporated in vacuo to give 2.14 g of Int. 314, white solid (92%).

The synthetic route of 3438-46-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; MEVELLEC, Laurence, Anne; PASQUIER, Elisabeth, Therese, Jeanne; DESCAMPS, Sophie; MERCEY, Guillaume, Jean, Maurice; WROBLOWSKI, Berthold; VIALARD, Jorge, Eduardo; MEERPOEL, Lieven; JEANTY, Matthieu, Ludovic; JOUSSEAUME, Thierry, Francois, Alain, Jean; WO2015/144799; (2015); A1;,
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Synthetic Route of 1004-38-2, 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.1004-38-2, name is 2,4,6-Triaminopyrimidine, molecular formula is C4H7N5, molecular weight is 125.13, as common compound, the synthetic route is as follows.

General procedure for thiocyanation of aminopyrimidine derivatives: Ammonium thiocyanate (3 mmol) and iodine (1.0 mmol) are added at room temperature to a stirred solution of the corresponding aminopyrimidine derivative (1.0 mmol) in methanol (10 mL). After completion of the reaction (TLC control), a sodium thiosulfate solution [20% (w/v)] is added to destroy the remaining iodine. The solid formed is filtered off, washed with water, and recrystallized from a methanol/water solution. For more details see Table 1 and Supplementary data.

Statistics shows that 1004-38-2 is playing an increasingly important role. we look forward to future research findings about 2,4,6-Triaminopyrimidine.

Reference:
Article; Rodriguez, Ricaurte; Camargo, Patricia; Sierra, Cesar A.; Soto, Carlos Y.; Cobo, Justo; Nogueras, Manuel; Tetrahedron Letters; vol. 52; 21; (2011); p. 2652 – 2654;,
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Reference of 3167-50-8, 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. 3167-50-8, name is 2-Aminopyrimidine-5-carboxylic acid, molecular formula is C5H5N3O2, 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.

In a 100mL one-neck flask,2-amino-5-pyrimidinyl acid (1.39g, 10.0mmol) was dissolved in DMF (25mL), wasadded 1- (3-dimethylaminopropylAminopropyl) -3-ethylcarbodiimidehydrochloride (191mg, 1.0mmol) and triethylamine (0.42mL, 3.0mmol), stirred for10min, add1 -tert-butoxycarbonyl-piperazine (135mg,1.0mmol), the reaction at room temperature 12h. The organic solvent wasdistilled off under reduced pressure, the residue was purified by columnchromatography (twoDichloromethane / methanol (V / V) = 10/1),to give a pale yellow oil (1.25g, 56.60%).

According to the analysis of related databases, 3167-50-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; East Sunshine Pharmaceutical Co., Ltd.; Liu, Bing; Zhang, Yingjun; Nie, Linlin; Bai, Shun; Zheng, Changchun; Nie, biao; Li, Zhiyong; Tan, Yumei; (61 pag.)CN105294737; (2016); A;,
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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. 137281-39-1, name is 4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid

Weigh 4-[2-(2-amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic acid (60 g 0.2 mol) Add to a 500ml four-neck bottle,Add 200ml of DMF and 60.6g of triethylamine to the temperature to 30 C and stir to dissolve.Benzyl chloride (0.3 mol) was added dropwise, and the mixture was heated to 60 C for 1 hour, and DMF was evaporated to dryness under reduced pressure.Adjust the pH to 6 with dilute hydrochloric acid, stir the crystals, cool down to 0-5 C, filter, and dry the product.4-[2-(2-Benzylamino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic acid (molar yield 96.9%) , purity 99.4%).

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, 137281-39-1, 4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid.

Reference:
Patent; Lunan Pharmaceutical Group Co., Ltd.; Xia Mingjun; Zang Chao; (11 pag.)CN110305137; (2019); A;,
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