Pyrimidines

Electric Literature of 13036-57-2, 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.13036-57-2, name is 2-Chloro-4-methylpyrimidine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.

A solution of Lithium bis(trimethylsilyl)amide (1M in THF, 10.26mL, 10.26mmol) was added to a cooled (0C) solution of Methyl 3-((tert-butoxycarbonyl)amino)-2- fluorobenzoate (790mg, 2.93mmol) in THF (15mL). After lOmin of stirring, a solution of 2-chloro-4-methylpyrimidine (452mg, 3.52mmol) in THF (2mL) was slowly added and the reaction mixture was allowed to warm to 40C for lh. Aqueous saturated ammonium chloride was added to the medium. The aqueous layer was extracted with EtOAc (2 times). Combined organics were washed with brine, dried over sodium sulphate, filtered and the filtrate was concentrated under reduced pressure. Purification of the residue by flash chromatography on silica gel (cHex-EtOAc 1/0 to 0/1) afforded the title compound (880mg, 82%). LC/MS (ES+): 366.3-368.3 (M+l).

Statistics shows that 13036-57-2 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-4-methylpyrimidine.

Reference:
Patent; CELLIPSE; PRUDENT, Renaud; PAUBLANT, Fabrice; (74 pag.)WO2018/55097; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 7752-82-1, 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. 7752-82-1, name is 5-Bromopyrimidin-2-amine. A new synthetic method of this compound is introduced below.

A mixture of 5-bromo-pyrimidin-2-ylamine (0.8g, 4.59mmol), 4-bromophenyl boronic acid(1g, 4.97mmol), tetrakis(triphenylphosphine)palladium(0) (3OOmg, 0.259mmol), cesium carbonate (1.15g, 3.03mmol) was stirred in MeOH/H2O (20ml, 1/1 ) at reflux temperature overnight. The reaction was cooled to room temperature and diluted with EtOAc (200ml) and water (50ml). The organic layer was separated, dried over MgSO4, filtered and solvent evaporated yielding a residue which was purified on silica gel eluting with 85% v/vEtOAc/hexanes yielding product 81 as white solid. (0.7g, 63%). ESMS (MH, 250).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7752-82-1, 5-Bromopyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; SCHERING CORPORATION; WO2008/156739; (2008); A1;,
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. 89793-12-4, name is Ethyl 2-chloropyrimidine-5-carboxylate, the common compound, a new synthetic route is introduced below. Safety of Ethyl 2-chloropyrimidine-5-carboxylate

Example 1 Synthesis of 2-(diphenylamino)-N-(7-(hydroxyamino)-7-oxoheptyl) pyrimidine-5-carboxamide (Compound A) Synthesis of Intermediate 2 A mixture of aniline (3.7 g, 40 mmol), ethyl 2-chloropyrimidine-5-carboxylate 1 (7.5 g, 40 mmol), K2CO3 (11 g, 80 mmol) in DMF (100 ml) was degassed and stirred at 120 C. under N2 overnight. The reaction mixture was cooled to rt and diluted with EtOAc (200 ml), then washed with saturated brine (200 ml*3). The organic layer was separated and dried over Na2SO4, evaporated to dryness and purified by silica gel chromatography (petroleum ethers/EtOAc=10/1) to give the desired product as a white solid (6.2 g, 64%).

The synthetic route of 89793-12-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Acetylon Pharmaceuticals, Inc.; Quayle, Steven Norman; Jones, Simon Stewart; Anderson, Kenneth C.; Hideshima, Teru; US2015/105358; (2015); A1;,
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. 171887-03-9, name is N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide, molecular formula is C5H4Cl2N4O, 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. name: N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide

To a slurry of N-(2-amino-4,6-dichloro-5-pyrimidinyl) formamide (42g) in 2- propanol (500 ml), triethylamine (31.4g) was added at 230C. The slurry was heated to 75-8O0C. A solution of 4-amino-2-hydroxymethylbutan-l-ol (27gm, -95% purity) in a mixture of 2-propanol (120ml) and water (17.4 ml) was slowly added to the refluxing reaction mass in about 60 minutes. The mixture was stirred at 75-8O0C for 2 hrs for completion of the reaction and concentrated under reduced pressure. The resulting residue was diluted with methanol (900 ml) and treated with activated charcoal (2 g). The solution was filtered through celite and the residue was washed with methanol (80 ml). To the filtrate 10% Palladium on Carbon (50% water paste, 6g) was added. The slurry was transferred to a hydrogenation vessel and hydrogenated at ~50C and 5-6 kg/cm2 for 20 hrs. After completion of the reaction, catalyst was removed by filtration and the residue washed with methanol (50 ml). The combined filtrate was concentrated to ~130 ml under reduced pressure at < 5O0C. The concentrate was cooled to -230C and hydrogen chloride solution in methanol (54gm, 17% w/w) was added. The light yellow coloured solution was stirred for 5-10 minutes at -230C and trimethylorthoformate (96.8Og) was added. The solution was heated to about 450C and continued stirring at 45-5O0C for 4 hrs. Thereafter, a mixture of 4gm concentrated hydrochloric acid and 6 g water was added. Stirring was continued at 45-5O0C for 90 minutes, product start crystallizing after 20 minutes of stirring. The suspension was cooled to 5-80C, stirred for 60 minutes. Product was filtered and washed with prechilled methanol (30ml, O0C), and dried at 5O0C under reduced pressure to constant weight yield 27.4 g: off white powder, HPLC purity > 98.1%.

With the rapid development of chemical substances, we look forward to future research findings about 171887-03-9.

Reference:
Patent; AUROBINDO PHARMA LIMITED; WO2008/72074; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 20737-41-1, 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 20737-41-1, name is 4-Aminopyrimidine-5-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

(Step 1) Methyl 4-aminopyrimidine-5-carboxylate (0191) (0192) 4-Aminopyrimidine-5-carboxylic acid (10.0 g, 71.9 mmol) was dissolved in methanol (100 ml), the reaction solution was cooled to 0 C., then concentrated sulfuric acid (25 ml) was slowly added dropwise, and the resulting mixture was stirred at 85 C. for 12 hours. The reaction liquid was concentrated under reduced pressure, then the resulting solution was diluted with water, and sodium hydrogen carbonate (10.0 g) was added. The resulting mixture was extracted with ethyl acetate (80 ml¡Á4), the extracts were combined, washed with a saturated saline solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, the obtained residue was stirred in a mixed solvent (petroleum ether:ethyl acetate=8:1), and the precipitated solid was filtered and dried to obtain the title compound (9.90 g, 90%). (0193) 1H-NMR (400 MHz, DMSO-d6): delta 8.72 (s, 1H), 8.53 (s, 1H), 8.04 (s, 1H), 7.62 (s, 1H), 3.83 (s, 3H); MS (ESI) m/z 154 (M+H)+

According to the analysis of related databases, 20737-41-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ajinomoto Co., Inc.; UENO, Hirokazu; YAMAMOTO, Takashi; MIYAZAWA, Tomoko; SHINKAI, Kenji; ARISAKA, Harumi; TAKANOHASHI, Toshiyuki; (122 pag.)US2016/244451; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 10070-92-5, 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. 10070-92-5, name is Pyrimidine-5-carbaldehyde. A new synthetic method of this compound is introduced below.

A mixture of the product from Preparative Example 28 (1.16 g, 4.00 mmol), pyrimidine-5-carboxaldehyde (540 mg, 5.00 mmol), and Ti(OiPr)4 (4.54 g, 16.0 mmol) in anhydrous THF (20 mL) was stirred under N2 at 50 C. for 3 hr. The mixture was cooled to 25 C., NaBH3CN (1.26 g, 20.0 mmol) was added, and the mixture was stirred at 25 C. for 30 min. The mixture was poured into 5% aqueous NaOH (500 mL), saturated aqueous NaCl (50 mL) was added, and the mixture was extracted with CH2Cl2 (3¡Á100 mL). The combined extracts were dried over Na2SO4, filtered, and the solvent was evaporated. The residue was purified by column chromatography on silica gel with CH2Cl2/MeOH/conc. aqueous NH4OH (20:1:0.1). Pale yellow solid (410 mg, 27%) was obtained. M. P. 201-203 C., LCMS: MH+=383.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10070-92-5, Pyrimidine-5-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; SCHERING CORPORATION; US2004/63715; (2004); A1;,
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. 6320-15-6, name is 4-Chloro-2,6-dimethoxypyrimidine, the common compound, a new synthetic route is introduced below. SDS of cas: 6320-15-6

piperazine (1.23 g, 14.32 mmol) was treated with 6-chloro-2,4-dimethoxy pyrimidine (0.5 g, 2.86 mmol) in acetonitrile (5 mL) and stirred at room temperature for 6 hours. Subsequently the reaction mixture was poured onto ice-cold water (25 mL) and extracted with ethyl acetate (25 mL). The organic layer was washed with aqueous sodium bicarbonate solution and evaporated to furnish the required compound.

The synthetic route of 6320-15-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORCHID RESEARCH LABORATORIES LIMITED.; US2007/167413; (2007); A1;,
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. 3435-25-4, name is 4-Chloro-6-methylpyrimidine, the common compound, a new synthetic route is introduced below. name: 4-Chloro-6-methylpyrimidine

Make BA-1 (1.00 g, 7.78 mmol)And Ni(dppe)Cl2 (82 mg, 0.16 mmol)The solution in anhydrous Et 2 O (5 mL) was cooled to -10 C.Then, n-propyl magnesium bromide was added dropwise and the mixture was stirred at -10 C for 2 h.The mixture was quenched with saturated aq. The crude BA-2 can be used without further processing.

The synthetic route of 3435-25-4 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; (169 pag.)TW2018/38997; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 39906-04-2, 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 39906-04-2, name is 4,6-Dichloro-2-methylpyrimidin-5-amine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of 5-amino-4,6-dichloro-2-methyl-pyrimidine (5.6mmol) in acetonitrile (20mL), Cs2CO3 (11.2mmol) and the suitable arylisothiocyanate (5.6mmol) were added. The suspension was stirred at 50C until disappearance (5-30h) of the starting materials (TLC monitoring: eluting system ciclohexane/ethyl acetate 7:3). Then, another 50mL of acetonitrile was added and the suspension was heated at 50C and filtered while hot. The filtrate, after the addition of 5g of silica gel (70-230 mesh), was stirred at room temperature for 20min and filtered. The solvent was removed in vacuum, and the residue was collected and recrystallized.

According to the analysis of related databases, 39906-04-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Varano, Flavia; Catarzi, Daniela; Squarcialupi, Lucia; Betti, Marco; Vincenzi, Fabrizio; Ravani, Annalisa; Varani, Katia; Dal Ben, Diego; Thomas, Ajiroghene; Volpini, Rosaria; Colotta, Vittoria; European Journal of Medicinal Chemistry; vol. 96; (2015); p. 105 – 121;,
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.22536-61-4, name is 2-Chloro-5-methylpyrimidine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.Recommanded Product: 2-Chloro-5-methylpyrimidine

2-chloro-5-methylpyrimidine (200mg, 1.556 mmol) was dissolved in carbon tetrachloride (5 mL), NBS (332 mg, 1.867 mmol) and benzoyl peroxide (18.84 mg, 0.078 mmol) were added , and the resulting mixture was heated and refluxed for overnight. The reaction solution was returned to RT, concentrated under reduced pressure and purified by ISCO (Hexanes/AcOEt, 0-100%) to afford the title compound (Intermediate 202a, 116 mg, 0.559 mmol, 35.9 % yield) as a white solid. LC-MS (Method A5): 1.62 min, [M + H]+= 206.9 and 208.9; lH NMR (500 MHz, CDC13) delta 8.69 (s, 2H), 4.44 (s, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22536-61-4, 2-Chloro-5-methylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; UNIVERSITE DE MONTREAL; BRISTOL-MYERS SQUIBB COMPANY; PRIESTLEY, Eldon, Scott; REZNIK, Samuel, Kaye; RUEDIGER, Edward, H.; GILLARD, James, R.; HALPERN, Oz, Scott; JIANG, Wen; RICHTER, Jeremy; RUEL, Rejean; TRIPATHY, Sasmita; YANG, Wu; ZHANG, Xiaojun; (642 pag.)WO2018/5591; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia