Day: January 22, 2021

Adding a certain compound to certain chemical reactions, such as: 7752-82-1, 5-Bromopyrimidin-2-amine, 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, Computed Properties of C4H4BrN3, blongs to pyrimidines compound. Computed Properties of C4H4BrN3

Method 1 [0079] S idine-2-ylamine[0080] To a dry 500-mL flask was added 2-amino-5-bromopyrimidine (10 g, 57.5 mmol), potassium acetate (16.9 g, 172 mmol), 4,4,5, 5-tetramethyl-2-(4,4,5,5-tetramethyl-l, 3,2- dioxaborolan-2yl)-l ,3,2-dioxaborolane (16.1 g, 63.0 mmol) and dioxane (300 mL). Argon was bubbled through the solution for 15 minutes, at which time dichloro[l,l’- bis(diphenylphosphino)ferrocene] palladium (II) dichloromethane adduct (Pd(dppf)Cl2 CH2CI2) (2.34 g, 2.87 mmol) was added. The reaction mixture was refluxed in a 115 C oil bath for 4 hours under argon. After cooling to room temperature, EtOAc (500 mL) was added and the resulting slurry was sonicated and filtered. Additional EtOAc (500 mL) was used to wash the solid. The combined organic extracts were washed with H20 (2×300 mL), NaCl(Sat.) (300 mL), dried over Na2S04, and filtered through a 5 cm pad of silica gel.Additional EtOAc was used to flush product. After the solvent was concentrated, the crude was treated with a mixture of 1 :3 dichloromethane and hexane (40 mL), filtered and washed with hexane yielding a light yellow solid (8.5 g, 75%). LCMS (m/z): 140 (MH+ of boronic acid, deriving from product hydrolysis on LC). ? NMR (CDC13): delta 8.58 (s, 2H), 5.74 (s, 2H), 1.32 (s, 12H).

The synthetic route of 7752-82-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; ZHAO, Jean J.; WANG, Qi; WO2012/109423; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 33034-67-2, 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. 33034-67-2, name is 2-Chloro-4-(trifluoromethyl)pyrimidine. A new synthetic method of this compound is introduced below.

Preparative Example 3 N-(3-Bromophenyl)-4-(trifluoromethyl)pyrimidin-2-amine A solution of 3-bromoaniline (250 g, 1.46 mol) in dioxane (2.5 L) was prepared, and 2-chloro-4-(trifluoromethyl)pyrimidine (267 g, 1.47 mol) and methanesulfonic acid (155 g, 1.61 mol) were added sequentially. The resulting solution was heated to 100 ¡ãC overnight. The resulting mixture was cooled and concentrated under reduced pressure. The residue was adjusted to pH 7-8 with aqueous sodium bicarbonate solution. The solid was filtered, and the filtrate was extracted with EtOAc (4×500 mL) The organic layers were combined, washed with water (2 x 2 L), dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford N-(3-bromophenyl)-4-(trifluoromethyl)pyrimidin-2-amine as a light yellow solid. MS APCI [M + 3]+ m/z 319. NMR (500 MHz, CDCI3) delta 8.68 (d, / = 4.9 Hz, 1 H), 7.95 (s, 1 H), .53-7.50 (m, 1 H), 7.44 (br s, 1 H), 7.22 (m, 2 H), 7.08 (d, / = 4.9 Hz, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,33034-67-2, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; MACHACEK, Michelle R.; ROMEO, Eric T.; KATTAR, Solomon D.; CHRISTOPHER, Matthew; ALTMAN, Michael D.; NORTHRUP, Alan B.; ELLIS, John Michael; BOYLE, Brendan O’; DONOFRIO, Anthony; GRIMM, Jonathan; REUTERSHAN, Michael H.; CHILDERS, Kaleen Konrad; OTTE, Ryan D.; CASH, Brandon; DUCHARME, Yves; HAIDLE, Andrew M.; SPENCER, Kerrie; VITHARANA, Dilrukshi; WU, Lingyun; ZHANG, Li; ZHANG, Peng; BEAULIEU, Christian; GUAY, Daniel; WO2014/48065; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1546-78-7, Adding some certain compound to certain chemical reactions, such as: 1546-78-7, name is 4-Hydroxy-6-(trifluoromethyl)pyrimidine,molecular formula is C5H3F3N2O, 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 1546-78-7.

Add 6-(trifluoromethyl)pyrimidin-4-ol (1.5 g, 9.15 mmol) and oxalyl chloride (2.3 mL, 22.9 mmol) to EtOAc (15 mL), then add 5 drops of DMF. Heat the mixture to reflux for 2 hrs. After reaction, partition between EtOAc and brine, separate the organic layer; dry the organic layer over anhydrous Na2S04. Transfer the organic solution to a sealed tube, add a solution of NH3 in methanol (7M, lOmL), seal the tube, heat at 70C for 15 hrs. Cool to room temperature; concentrate under reduced pressure to get the crude product. Purification by chromatography (silica gel, EtOAc_PE=2:l) affords the target compound (920 mg, 61.3%).

According to the analysis of related databases, 1546-78-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CROWN BIOSCIENCE INC. (TAICANG); ZHANG, Deyi; ZHANG, Ruihao; ZHONG, Boyu; SHIH, Chuan; WO2014/418; (2014); 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. 4595-61-3, name is Pyrimidine-5-carboxylic acid, molecular formula is C5H4N2O2, 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. HPLC of Formula: C5H4N2O2

5-Pyrimidinecarboxylic acid (500mg) in thionyl chloride (5mL) was stirred at 110¡ãC5 under nitrogen for 1h. The solvent was evaporated under vacuum to give 5-pyrimidinecarbonyl chloride as a brown oil (505mg). (4-Bromo-2-fluorophenyl)(iodo)zinc intetrahydrofuran (0.5M, 7.0ml_) was added slowly to a stirred mixture of the acid chloride(500mg) and tetrakis(triphenylphosphine)palladium(0) (203mg) in tetrahydrofuran (3mL) atroom temperature under nitrogen then stirred at room temperature for 1h. Aqueous10 ammonium chloride (1M, 5mL) was added and the mixture was absorbed onto silica andpurified by chromatography on a silica column eluting with a cyclohexane/ethyl acetategradient to give the title compound (712mg).LC-MS: Rt 2.65min.

With the rapid development of chemical substances, we look forward to future research findings about 4595-61-3.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/73189; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 5194-32-1 , The common heterocyclic compound, 5194-32-1, name is 2-Methylpyrimidine-5-carboxylic acid, molecular formula is C6H6N2O2, 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.

At room temperature, to the containing 1-(3-(3-amino-5-chloro-2-methylbenzyl)-3,8-diazabicyclo[3.2.1]octan-8-yl)-2-cyclobutylethan-1-one (150.0 mg, 0 . 42 mmol) in dichloromethane solution, adding N, N – diisopropyl ethylamine (160.8 mg, 1 . 25 mmol) and 2-methyl-5-pyrimidine formic acid (63.5 mg, 0 . 46 mmol), addition of HATU (399.2 mg, 1 . 05 mmol), after the adding of, stirring at room temperature the reaction for 10 hours. After the reaction is complete, the solvent is removed under reduced pressure, the residue by silica gel column chromatography (petroleum ether: ethyl acetate=5:1 – 1:1) and thick preparation plate purification to obtain white solid compound 95.0 mg, yield 46.9%.

The synthetic route of 5194-32-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fudan University; Wang Yonghui; Tian Jinlong; Yu Mingcheng; (29 pag.)CN109134476; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 19875-04-8, 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.19875-04-8, name is 2-Methylpyrimidin-4(3H)-one, molecular formula is C5H6N2O, molecular weight is 110.11, as common compound, the synthetic route is as follows.

(b) 11 g of 2-methyl-4-pyrimidone were introduced into 50 ml of phosphorus oxychloride, and the mixture was heated at 80 C. until a clear solution was produced. Excess phosphorus oxychloride was removed by distillation in vacuo, and the residue was poured into ice-water. While cooling, the solution was neutralized with potassium hydroxide solution and extracted with dichloromethane. The organic extracts were dried (Na2 SO4) and concentrated in vacuo, and column chromatography resulted in 8 g of 4-chloro-2-methylpyrimidine (melting point 50-60 C.).

Statistics shows that 19875-04-8 is playing an increasingly important role. we look forward to future research findings about 2-Methylpyrimidin-4(3H)-one.

Reference:
Patent; Hoechst Aktiengesellschaft; US4956366; (1990); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 157335-93-8 , The common heterocyclic compound, 157335-93-8, name is 4,6-Dimethylpyrimidine-5-carboxylic acid, molecular formula is C7H8N2O2, 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.

EXAMPLES; Example 1: Preparation of 1-(2,4-dimethylpyrimidine-5-carbonyl)-4- piperidone – Compound IV:; To a suspension solution of 90.0 g of 4,6-dimethylpyrimidine-5- carboxylic acid (I) and a catalytic amount of dimethylformamide (0.45 ml_) in CH3CN (630 ml_) was slowly added oxalyl chloride (78.8 g) at -50C to 50C. The reaction was then aged at O0C for 2 hours. EPO In a separate flask, a heterogeneous mixture of K3PO4 (136.1 g), K2HPO4 (205.9 g) in water (270 ml_) and CH3CN (540 ml_) at O0C was added to a solution of 99.8 g of 4-piperidone monohydrate hydrochloride (III) in water (135 ml_). The reaction mixture was agitated at O0C for 2 hours.

The synthetic route of 157335-93-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2006/74264; (2006); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 856972-65-1 ,Some common heterocyclic compound, 856972-65-1, molecular formula is C6H8ClN3O, 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 5 mL vial containing a stir bar, 3-(2-aminopyrimidin-5-yl)-6-cyclobutyl-2-fluorophenol (80 mg, 0.31 mmol) and 2-chloropyrimidine (41 mg, 0.34 mmol) were added Cs2CO3 (203 mg, 0.62 mmol) and DMSO (0.8 mL). The resultant mixture was stirred at 120 Celsius for approximately 1 hour via microwave irradiation. The reaction mixture was cooled to room temperature before passing the mixture through a syringe filter and subjecting the filtrate to FCC to afford the title compound (81 mg, 78%). The title compound was prepared using conditions similar to those described in Example 160 heating via microwave irradiation for 2 hours and using 4-chloro-6-(methoxymethyl)pyrimidin-2-amine. MS (ESI): mass calcd. for C20H21FN6O2, 396.17; m/z found, 397.1 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 8.48 (d, J=1.0, 2H), 7.25-7.15 (m, 2H), 6.38 (s, 1H), 5.30 (s, 2H), 5.08 (s, 2H), 4.35 (s, 2H), 3.66-3.53 (m, 1H), 3.48 (s, 3H), 2.29-2.06 (m, 4H), 2.05-1.89 (m, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,856972-65-1, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Eccles, Wendy; Fitzgerald, Anne E.; Hack, Michael D.; Hawryluk, Natalie A.; Jones, William M.; Keith, John M.; Krawczuk, Paul; Lebsack, Alec D.; Liu, Jing; Mani, Neelakandha S.; McClure, Kelly J.; Meduna, Steven P.; Rosen, Mark D.; US2014/221310; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1004-38-2, 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. 1004-38-2, name is 2,4,6-Triaminopyrimidine, molecular formula is C4H7N5, 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.

General procedure: A mixture of 2,4,6-triaminopyrimidine 1 (1.0 mmol), 3-(2-cyanoacetyl)indole 2 (1.0 mmol), appropriate aromatic aldehyde (1.0 mmol) and indium chloride (0.05 mmol) in ethanol (5.0 mL) were subjected to microwave irradiation for 10 min at 120 C. After completion of the reaction (monitored by TLC using a dichloromethane-ethanol (9:1) mixture as the mobile phase), the reaction mixture was cooled and filtered. The solid product obtained was initially washed with ethanol, and finally recrystallized from ethanol.

According to the analysis of related databases, 1004-38-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Enriz, Ricardo D.; Tosso, Rodrigo D.; Andujar, Sebastian A.; Cabedo, Nuria; Cortes, Diego; Nogueras, Manuel; Cobo, Justo; Vargas, Didier F.; Trilleras, Jorge; Tetrahedron; vol. 74; 49; (2018); p. 7047 – 7057;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 26305-13-5, 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.26305-13-5, name is 2,4-Dihydroxy-5,6-dimethylpyrimidine, molecular formula is C6H8N2O2, molecular weight is 140.14, as common compound, the synthetic route is as follows.

Example 15. A/-hexyl-5,6-dimethyl-2,4-dioxo-pyrimidine-1 -carboxamide Triphosgene (0.12 g, 0.71 mmol) was added to dry pyridine (2.0 mL) at 0 C. The mixture was stirred for 10 min, then a solution of 5,6-dimethyluracil (0.10 g, 0.71 mmol) in dry pyridine (3.0 mL) was added dropwise. The pale yellow suspension formed was stirred at room temperature for 5 hrs, then cooled to 0 C before adding hexylamine (0.10 mL, 0.71 mmol). The reaction mixture was stirred at room temperature for 18 hrs. Water (30 mL) was added and the product extracted with EtOAc (3 x 30 mL). The combined organic layer was dried over Na2S04 and the solvent removed under reduced pressure. The crude was purified by column chromatography using a Teledyne ISCO apparatus (cyclohexane:EtOAc 90:10) to afford the title compound (0.02 g, 6%) as white powder. 1 H NMR (400 MHz, CDCIs): delta 0.90 (t, J = 6.6 Hz, 3H), 1 .25-1 .38 (m, 6H), 1 .53-1 .67 (m, 2H), 1 .83 (br s, 3H), 2.19 (br s, 3H), 3.30 (dt, J = 5.6, 7.0 Hz, 2H), 7.42-7.65 (m, 1 H), 9.68 (br s, 1 H). 13C NMR (101 MHz, CDCI3): delta 9.00, 13.34, 15.77, 22.35, 26.12, 28.91 , 31 .30, 40.70, 104.68, 146.24, 149.35, 162.15, 164.20. MS (ESI) m/z: 266 [M-H]”.

Statistics shows that 26305-13-5 is playing an increasingly important role. we look forward to future research findings about 2,4-Dihydroxy-5,6-dimethylpyrimidine.

Reference:
Patent; FONDAZIONE ISTITUTO ITALIANO DI TECNOLOGIA; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; UNIVERSITA’ DEGLI STUDI DI PARMA; PIOMELLI, Daniele; REALINI, Natalia; MOR, Marco; PAGLIUCA, Chiara; PIZZIRANI, Daniela; SCARPELLI, Rita; BANDIERA, Tiziano; WO2013/178576; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia