Tag: M.W:100-200

Adding a certain compound to certain chemical reactions, such as: 769-42-6, 1,3-Dimethylbarbituric acid, 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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

General procedure: To a solution of L-proline-melamine complex (3 mol%) in DMSO (2 mL) was added dimedone 0.025 mg (0.178 mmol), malononitrile (1 equiv) and benzaldehyde / isatin (1 equiv) and stirred at room temperature for 1-20 min. After completion of the reaction (monitored by TLC), ethyl acetate was added stirring and continued for another 5 min. The precipitate formed was filtered. Evaporation of solvent gave the crude product which was recrystallized using ethanol to give the pure compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,769-42-6, 1,3-Dimethylbarbituric acid, and friends who are interested can also refer to it.

Reference:
Article; Nagaraju, Sakkani; Paplal, Banoth; Sathish, Kota; Giri, Santanab; Kashinath, Dhurke; Tetrahedron Letters; vol. 58; 44; (2017); p. 4200 – 4204;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 5750-76-5, 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. 5750-76-5, name is 2,4,5-Trichloropyrimidine, molecular formula is C4HCl3N2, 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.

A mixture of 2- (isopropylsulfonyl) aniline (1 g, 5 mmol)And 2,4,5-trichloropyrimidine (1.1 g, 6 mmol)Was dissolved in N, N-dimethylformamide (30 mL)Sodium hydride (60%, 0.4 g, 10 mmol) was added,25 C for 12 hours.(30 mL x 3), the organic phase was combined, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated in vacuo,The crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 25: 1)The product (0.8 g, yield 46%) was obtained.

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 5750-76-5, 2,4,5-Trichloropyrimidine.

Reference:
Patent; Shandong Xuanzhu Pharma Co., Ltd.; Wu, Yongqian; (21 pag.)CN106146525; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 16019-33-3 , The common heterocyclic compound, 16019-33-3, name is 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde, molecular formula is C6H4Cl2N2O, 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.

(1R,2S,3R,5R)-3-Amino-5-(hydroxymethyl)cyclopentane-1,2-diol hydrochloride (40 g, 218 mmol) was dissolved at room temperature in methanol (400 mL) and 2,2-dimethoxypropane (54 mL, 436 mmol), and methanesulfonic acid(14 mL, 218 mmol) was added thereto dropwise in an ice bath with stirring so as to keep the internal temperature at 7C or lower. After the mixture was stirred in an ice bath for 5 minutes and at room temperature overnight, triethylamine (122 mL, 872 mmol) was added thereto dropwise in an ice bath so as to keep the internal temperature at 10C or lower. After the mixture was stirred in an ice bath for 5 minutes and at room temperature for 30 minutes, the solvent was distilled off under reduced pressure, thereby obtaining the title compound as a crude isomeric mixture (102 g). LCMS (ESI) m/z 188 [M+H]+ The crude isomeric mixture (102 g) of ((3aR,4R,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methanol and (4aR,6R,7S,7aR)-6-amino-2,2-dimethylhexahydrocyclopenta[d][1,3]dioxin-7-ol obtained in step 1 of Reference Example 93, and 2-(4,6-dichloropyrimidin-5-yl)acetaldehyde (46 g, 240 mmol) was suspended in 2-butanol (400 mL). Then, triethylamine (61 mL, 436 mmol) was added thereto at room temperature, and the reaction solution was stirred at 80C overnight. After the reaction solvent was distilled off under reduced pressure, the residue was partitioned with the addition of ethyl acetate and an aqueous sodium hydrogen carbonate solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline, and dried over sodium sulfate, followed by distilling off the solvent, thereby obtaining the title compound as a crude isomeric mixture (72 g). LCMS (ESI) m/z 324 [M+H]+

The synthetic route of 16019-33-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Taiho Pharmaceutical Co., Ltd.; ISHIDA, Keiji; (139 pag.)EP3395345; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 108-53-2, 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.108-53-2, name is 2-Aminopyrimidin-4(1H)-one, molecular formula is C4H5N3O, molecular weight is 111.102, as common compound, the synthetic route is as follows.

In a three neck IL round bottom flask equipped with reflux condenser was added 2-amino- 4(3H)-pyrimidinone A.ll (10Og, 0.9 mol) (available from Toronto Research Chemicals) followed by POCl3 (168 ml, 1.800mol) at room temperature and under an atmosphere of N2. To this was cautiously added ClSO3H (4.8ml, 72.01 mmol). The solution was heated to 950C for 4 hrs, before it was cooled to room temperature. The solution was then cooled in an ice bath before it was poured into 700ml of ice water with vigorous stirring. Adjusted the pH to ~7 with NH4OH (30% by weight) (temperature was held below 2O0C). A tan colored solid was collected by filtration. The solid was dried under vacuum at 7O0C overnight to afford 4-chloro- 2-pyrimidinamine A.12 (108g, 92%) as an off white solid.1H NMR (400 MHz, (CD)3SO) delta 8.17 (d, J = 5.2 Hz, IH), 7.07 (br s, 2H), 6.64 (d, J = 5.2 Hz, IH); ESI MS: M + H+ 130.0 m/z.

Statistics shows that 108-53-2 is playing an increasingly important role. we look forward to future research findings about 2-Aminopyrimidin-4(1H)-one.

Reference:
Patent; AMGEN INC.; WO2009/158011; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1820-81-1, 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.1820-81-1, name is 5-Chlorouracil, molecular formula is C4H3ClN2O2, molecular weight is 146.53, as common compound, the synthetic route is as follows.

Example 15 N4-[(trans-4-aminocyclohexyl)methyl]-5-chloro-N2-[2-(trifluoromethoxy)benzyl]pyrimidine-2,4-diamine To a suspension of 5-chlorouracil (15.0 g, 102.4 mmol) in POCl3 (50 mL, 326.1 mmol) was added N,N-diethylaniline (7.5 mL). The reaction mixture was heated at 110 C. for 24 h. The reaction mixture was cooled to room temperature and concentrated in vacuo to about 25 mL. The resulting residue was then poured into ice and stirred until all the ice melted. The aqueous layer was extracted with ether (*3). The combined organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The resulting residue was distilled under vacuum at ~90 C. to afford 12.5 g (81%) of 5-chloro-2,4-dichloropyrimidine.

The chemical industry reduces the impact on the environment during synthesis 1820-81-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; US2006/25433; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 10320-42-0, 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 10320-42-0, name is 2-Chloro-5-nitropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

first step:A dry 50 mL reaction jar was vacuumed three times with nitrogen.After adding N-methylaniline (107 mg, 1.0 mmol, 1.0 equiv) to the reaction jar,Add 10.0 mL of dried acetonitrile and stir until N-methylaniline is completely dissolved.Then 2-chloro-5-nitropyrimidine (0.1593 g, 1.0 mmol, 1.0 equiv) was added to the reaction flask.The entire mixture was reacted under nitrogen pressure for 4-5 hours.The reaction detects the progress of the reaction by TLC.The reaction can be stopped if it is detected that all the aniline is completely reacted.The experimental treatment is to drain the solution in the reaction;The solute in the reaction flask was dissolved with ethyl acetate.And transferred to a 100 mL round bottom flask,Add 2 mL (200-300 mesh) of silica gel to the round bottom flask for spin-drying (petroleum ether and acetic acid B)Ester) over silica gel in the column.The intermediate product was pale yellow crystals N-methyl-5-nitro-N-phenylpyrimidin-2-amine (197 mg, 86% yield).

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 10320-42-0, 2-Chloro-5-nitropyrimidine.

Reference:
Patent; Jinan University; Feng Pengju; Chen Tianfeng; Chen Junfeng; Huang Yifeng; (25 pag.)CN108148005; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 461-98-3, 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.461-98-3, name is 2,6-Dimethylpyrimidin-4-amine, molecular formula is C6H9N3, molecular weight is 123.16, as common compound, the synthetic route is as follows.

The mixture of 4-bromo-7-fluoro-2-(2,6-dichlorophenyl)-lH-imidazo[4,5-c]pyridine (50 mg, 0.14 mmol), 2,6-dimethylpyrimidine-2 -amine (22 mg, 0.18 mmol), Pd2(dba)3 (4 mg, 0.0040 mmol), XantPhos (2 mg, 0.002 mmol), Cs2C03 (90 mg, 0.28 mmol) in 1,4-Dioxane (10 mL) and DME (2 mL) was degassed with N2 for 1 min. The resulting mixture was irradiated in a microwave reactor at 170 C for 2 hrs and cooled to room temperature. The mixture was filtered with Celite and the filtrate was concentrated and purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm x 20 mm x 2, gradient: CH3CN / 10 mm/L NH4HCO3, 17 min) to give the desired product (27 mg, yield: 48%). ¾ NMR (DMSO- 6, 500 MHz): delta 8.30 (d, J = 6.0 Hz, 1H), 7.95 (s, 1H), 7.61 (m, 4H), 2.39 (s, 3H), 2.34 (s, 3H). LC-MS(ESI) m/z: 404.4 [M+H+].

Statistics shows that 461-98-3 is playing an increasingly important role. we look forward to future research findings about 2,6-Dimethylpyrimidin-4-amine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; LAI, Yingjie; LIANG, Jun; MAGNUSON, Steven R.; TSUI, Vickie H.; ZHANG, Birong; ROBARGE, Kirk; WO2011/113802; (2011); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 6299-25-8, 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 6299-25-8 as follows.

LDA (2M in THF/n-heptane/ethylbenzene) (3.72 ml_, 28.2 mmol) was added dropwise to a solution of commercially available 4,6-dichloro-2-methylsulfanyl-pyrimidine (5 g, 25.63 mmol) in anhydrous THF (30 ml_) at -78 C under a nitrogen atmosphere and the mixture stirred for 1 hour. Ethyl chloroformate (2.7 ml_, 28.24 mmol) was added via syringe and the mixture stirred at -78 C for a further 2 hours and then allowed to warm to room temperature. The reaction was quenched by addition of saturated aqueous ammonium chloride solution (50 ml_) and extracted with EtOAc (2 x 50 ml_). The combined organic portions were dried over MgSCU and the solvent removed in vacuo. Purification by column chromatography on silica eluting with a gradient of 1 to 2% EtOAc in petrol afforded the titled compound as a yellow solid. (1376) LC-MS (Method 3B): Rt 2.52 mins; MS m/z N/A [does not ionise] (1377) 1 H NMR (500 MHz, Chloroform-d) d 4.45 (q, J = 7.1 Hz, 2H), 2.58 (s, 3H), 1.41 (t, J = 7.1 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6299-25-8, its application will become more common.

Reference:
Patent; ADORX THERAPEUTICS LIMITED; MCCARTHY, Clive; MACLEOD, Calum; MOULTON, Ben; LENAGH-SNOW, Gabriel; (190 pag.)WO2019/122932; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 2240-25-7, 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. 2240-25-7, name is 4-Amino-5-bromopyrimidin-2(1H)-one, molecular formula is C4H4BrN3O, 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.

5-bromocytosine (95g, 0.5 mol), saturated sodium carbonate solution 200mL, 100 mL of dioxane was added the reaction flask was cooled to 10-15 °C dropwise loading fluorenylmethoxycarbonyl chloride (155.2g, 0.6mol mixed solu tion) and I00mL dioxane, the addition was complete, the reaction was warmed to room temperature and 3h, filtered, and the filter cake water (50mLX 2) washing and drying to give N- Fmoc-5-bromocytosine (196.7g , 95.4percent).

According to the analysis of related databases, 2240-25-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhejiang Xianfeng Technologies Co., Ltd; CHEN, XIAOPING; YAO, FUYOU; LU, WEI; XIAO, MUJIE; GAO, FEIFEI; (6 pag.)CN103819412; (2016); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 13036-50-5, 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. 13036-50-5, name is 2-Chloro-4-phenylpyrimidine. A new synthetic method of this compound is introduced below.

A mixture of 2-chloro-4-phenylpyrimidine (71 mg, 0.37 mmol), Intermediate 20 (100 mg, 0.34 mmol) and DIPEA (120 muIota_, 0.68 mmol) in NMP (1 mL) was heated at 130C for 3 hrs. The reaction mixture was allowed to cool to ambient temperature and diluted with water (10 mL). The crude product was extracted into diethyl ether (20 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on the Biotage Companion (12 g column, 0 to 100% diethyl ether in isohexane) to afford the title compound as a gum (65 mg). LCMS (Method A): Two peaks at 2.45 min and 2.66 min, 451 [M+H]+.1H NMR (400 MHz, DMSO-d6, 374 K) 8.36 (d, 0.8 H), 8.30 (bd, 0.2 H), 8.15-8.07 (m, 1 .6 H), 7.97 (bm, 0.3 H), 7.56-7.46 (m, 3.92 H), 7.46-7.24 (m, 7.38 H), 7.16-7.05 (m, 1.8 H), 6.33 (bs, 1 H), 4.41 (td, 1 H), 3.71 (m, 1 H), 3.50 (m, 1 .1 H), 3.26 (bm, 0.2 H), 2.84 (s, 0.3 H), 2.82 (s, 0.3 H), 2.63 (s, 0.3 H), 2.48 (s, 2.1 H), 1 .82 (bm, 0.7 H), 1.00 (d, 2.5 H), 0.78 (bd, 0.5 H), 0.56 (bs, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13036-50-5, 2-Chloro-4-phenylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; C4X DISCOVERY LIMITED; BLANEY, Emma Louise; MARTIN, Barrie Phillip; NOWAK, Thorsten; WATSON, Martin John; (212 pag.)WO2016/34882; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia