Pyrimidines

Electric Literature of 69206-89-9 ,Some common heterocyclic compound, 69206-89-9, molecular formula is C9H14N4, 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: To a slurry of 6?-bromo-8?-methyl-2?H-spiro[cyclohexane-1,3?-imidazo[1,5-a]pyridine]-1?,5?-dione (12) and aromatic aminederivatives (1.2 eq) in 1,4-dioxane was added Cs2CO3 (3 eq). Themixture was stirred at room temperature for 20 min under nitrogen.To the mixture was then added Pd(OAc)2 (0.1 eq) and Xantphos(0.2 eq). After stirred at room temperature for additional 20 minunder nitrogen, the mixture was heated at 95 C for 12 h undernitrogen. The mixture was concentrated in vacuo, added with water,stirred and filtered. The filter cake was dried and purified by flashcolumn chromatography.

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. 69206-89-9, 6-(Piperidin-1-yl)pyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yuan, Xinrui; Wu, Hanshu; Bu, Hong; Zheng, Peiyuan; Zhou, Jinpei; Zhang, Huibin; Bioorganic and Medicinal Chemistry; vol. 27; 7; (2019); p. 1211 – 1225;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 2927-71-1, 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.2927-71-1, name is 2,4-Dichloro-5-fluoropyrimidine, molecular formula is C4HCl2FN2, molecular weight is 166.9685, as common compound, the synthetic route is as follows.

2. Synthesis of Compound 3: Experimental Details: To a solution of compound 2 (1.04 g) in 15 ml of ethanol, 1.08 g (2 eq) of morphine was added dropwise at -10 C. in 15 min. The mixture was stirred for 0.5 h and heated at 50 C. for 15 min. After cooled and diluted with water (50 ml), compound 3 was obtained as a yellow solid powder after filtration.

Statistics shows that 2927-71-1 is playing an increasingly important role. we look forward to future research findings about 2,4-Dichloro-5-fluoropyrimidine.

Reference:
Patent; Housey, Gerad M.; US2010/16298; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1005-37-4 , The common heterocyclic compound, 1005-37-4, name is 6-Chloro-N4-methylpyrimidine-2,4-diamine, molecular formula is C5H7ClN4, 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.

2-Amino-4-anilino-6-methylaminopyrimidine was synthesized, via 2-amino-4-chloro-6-methylaminopyrimidine, with 2-amino-4,6-dichloropyrimidine as a starting material. 2-Amino-4,6-dichloropyrimidine (32.8 g), a 40% aqueous methylamine solution (34.5 mL), and ethanol (300 mL) were mixed, followed by stirring at an internal temperature of 70 C. for 4 hours. Subsequently, the solvent was concentrated under reduced pressure, and crystallization from acetonitrile was performed. The product was collected by filtration and was used without purification for the subsequent step. The crude product of 2-amino-4-chloro-6-methylaminopyrimidine, aniline (27.4 mL), methoxyethanol (100 mL), and hydrochloric acid (0.2 mL) were mixed, followed by stirring with heating at 120 C. for 3 hours. After cooling, the reaction solution was added to sodium bicarbonate water (500 mL)/ethyl acetate under ice cooling to extract the product with ethyl acetate. After concentration, purification by column chromatography (ethyl acetate/methanol) was performed to yield 18 g of 2-amino-4-anilino-6-methylaminopyrimidine. Synthesis was performed as in Synthetic example 1a-1 with 2-amino-4-anilino-6-methylaminopyrimidine, methyl m-methylbenzoate, and sodium methoxide. The product was purified by silica gel column chromatography using ethyl acetate/n-hexane and recrystallization from ethyl acetate/n-hexane to yield compound (6-14). (0405) The NMR spectrum of produced compound (6-14) is as follows. (0406) 1H-NMR (solvent: d6-DMSO, standard: tetramethylsilane) delta (ppm) 2.37 (3H, s) 2.75 (3H, d) 5.51 (1H, s) 6.87-6.91 (1H, m) 7.15-7.24 (2H, m) 7.34-7.38 (2H, m) 7.65-7.74 (4H, m) 8.95 (1H, s) 10.02 (1H, s)

The synthetic route of 1005-37-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJIFILM Corporation; YAMAMOTO, Aiko; TANAKA, Satoshi; NIORI, Teruki; NAGURA, Masato; NORO, Masaki; YOSHIDA, Aiko; FUKAGAWA, Nobutaka; KUWAYAMA, Yasukazu; (89 pag.)US2016/159750; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 22325-27-5 ,Some common heterocyclic compound, 22325-27-5, molecular formula is C6H8N2S, 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.

Sodium hypochlorite (30.9 mL, 60.0 mmol) was added dropwise with rapid stirring to a solution of 4,6-dimethylpyrimidine-2-thiol (1.40 g, 10.00 mmol) and CaCl2 (14 g) in CH2Cl2 (60 mL) and 1N HCl (55.0 mL, 55.0 mmol) at -23 C. After the addition was complete, the mixture was stirred for 15 min at -23 C. and the phases where separated. The organic layer was transferred to a 250 mL 3-necked flask which was then chilled to -23 C. and equipped with a cold finger (-70 C.). NH3 was bubbled through the reaction mixture for 15 min. and then the reaction was slowly allowed to warm to rt and stirred 16 h. The resulting white precipitate was separated by filtration and the filtrate was concentrated under vacuum to yield 4,6-dimethylpyrimidine-2-sulfonamide (1.003 g, 5.36 mmol, 53.6% yield) as white solid. 1H NMR (300 MHz, acetone-d6) delta ppm 7.43 (s, 1H), 6.63 (br s, 2H), 2.53 (s, 6H). LC-MS retention time 0.39 min; m/z 188 (MH+). LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Phenomenex-Luna 10 u C18 4.6¡Á50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 5 ml/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 2 min, a hold time of 1 min, and an analysis time of 3 min where solvent A was 10% MeOH/90% H2O/0.1% trifluoroacetic acid and solvent B was 10% H2O/90% MeOH/0.1% trifluoroacetic acid. MS data was determined using a Micromass Platform for LC in electrospray mode.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22325-27-5, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/130057; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 3001-72-7, 2,3,4,6,7,8-Hexahydropyrrolo[1,2-a]pyrimidine, 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, 3001-72-7, blongs to pyrimidines compound. Computed Properties of C7H12N2

General procedure: NaBPh4 (1 equiv) was added to a round-bottom flask and purged with nitrogen. Dry MeCN (to make a 0.2 M solution of NaBPh4) and the appropriate acyl chloride (1.04 equiv) were added and the resulting solution cooled to 0 C. DBN (1) (1 equiv) was added dropwise and a precipitate of NaCl began to form. The reaction was left to stir for 1 h before being warmed to room temperature and filtered through a pad of Celite, washing thoroughly with MeCN. The filtrate was then concentrated under reduced pressure and the resulting N-acyl DBN¡¤BPh4 salt purified by recrystallization from CH2Cl2 and hexane.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3001-72-7, its application will become more common.

Reference:
Article; Taylor, James E.; Williams, Jonathan M.J.; Bull, Steven D.; Tetrahedron Letters; vol. 53; 32; (2012); p. 4074 – 4076;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 52602-68-3, 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 52602-68-3 as follows.

General procedure: A mixture of the 4,5-diamino-6-chloro-N4-methylpyrimidine (6, 1mmol), the appropriate arylaldehyde (1.2mmol), acetic acid (2.3mmol) in methanol (4.3mL) was stirred at room temperature for 16h. The reaction mixture was concentrated to dryness under reduced pressure. The residue was azeotropically distilled with toluene (2¡Á4mL) and used directly in the next step. To the suspension in ethanol (6mL) of the crude imine, a solution of anhydrous FeCl3 (1mmol) in ethanol (3mL) was added. The mixture was stirred at 80C for the time stated below for each product. The solvent was removed and the 8-aryl-6-chloro-9-methyl-9H-purines 26-36 were obtained as pure compounds after silica gel flash chromatography and crystallization.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,52602-68-3, its application will become more common.

Reference:
Article; Lambertucci, Catia; Marucci, Gabriella; Dal Ben, Diego; Buccioni, Michela; Spinaci, Andrea; Kachler, Sonja; Klotz, Karl-Norbert; Volpini, Rosaria; European Journal of Medicinal Chemistry; vol. 151; (2018); p. 199 – 213;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia