Pyrimidines

Reference of 4595-61-3 , The common heterocyclic compound, 4595-61-3, name is Pyrimidine-5-carboxylic acid, molecular formula is C5H4N2O2, 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: General CouIinQ Procedure 4 COMU (1 .5 eq.) and DIPEA (4 eq.) were added to a stirred solutionCarboxylic acid A (1.0 eq.) and Amine B (1.2 eq.) in THF (2 mL) at RT. Thereaction mixture was stirred for 16 h at RT. The reaction mixture was then poured in ice water, stirred for 5 mm. and the resulting precipitate was filtered and washed with water. The cake was dried under reduced pressure and washed with diethyl ether and n-pentane to obtain a crude product. Additional purification by flash chromatography over silica was performedwhen necessary.

The synthetic route of 4595-61-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FROST BIOLOGIC, INC.; SIDDIQUI-JAIN, Adam; WO2015/127284; (2015); A2;,
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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. 944129-00-4, name is Methyl 6-amino-2-chloropyrimidine-4-carboxylate, the common compound, a new synthetic route is introduced below. Recommanded Product: 944129-00-4

Example 4 Preparation of methyl 6-amino-2-(4-chloro-2,3-difluorophenyl)-pyrimidine-4-carboxylate 2-(4-Chloro-2,3-difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.4 g, 5.1 mmol, 1.2 equiv) and methyl 6-amino-2-chloropyrimidine-4-carboxylate (800 mg, 4.3 mmol, 1.0 equiv) were sequentially added to a 20 mL Biotage microwave vessel, followed by cesium fluoride (1.3 g, 8.5 mmol, 2.0 equiv), palladium(II) acetate (38 mg, 0.17 mmol, 0.04 equiv), and sodium 3,3′,3″-phosphinetriyltribenzenesulfonate (190 mg, 0.34 mmol, 0.08 equiv). A 3:1 mixture of water:acetonitrile (8.5 mL) was added and the resulting brown mixture was placed in a Biotage microwave and heated at 150 C. for 5 m. The cooled reaction mixture was diluted with water (300 mL) and extracted with dichloromethane (5*100 mL). The combined organic layers were dried (magnesium sulfate), gravity-filtered, and concentrated under vacuum. The product was purified by flash chromatography (SiO2, 40% ethyl acetate in hexane) to afford the title compound as an off-white powder (880 mg, 68% yield): mp 192-195 C.; 1H NMR (300 MHz, CDCl3) delta 7.77 (m, 1H), 7.21-7.28 (m, 2H), 7.15 (s, 1H), 5.23 (br s, 2H), 4.00 (s, 3H); IR (neat film) 3493 (w), 3393 (m), 3342 (m), 3211 (s), 1730 (m), 1649 (m); ESIMS m/z 300 ([M+H]+).

The synthetic route of 944129-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DOW AGROSCIENCES LLC; US2012/190549; (2012); A1;,
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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. 130838-36-7, name is 2,6-Dichloropyrimidine-4,5-diamine, the common compound, a new synthetic route is introduced below. Recommanded Product: 130838-36-7

4, 5-Diamino-1,6-DICHLOROPYRIMIDINE (0,55MMMOL), prepared as described in Example 16, was suspended in water (2 ml) and heated to dissolve. After cooling the solution in the ice-water bath, acetic acid (2ml) was added to the solution. Sodium nitrite in water (0,5 MOL/1-2 ml) was added to this stirred solution at 0C during 15 minutes. After next 20 minutes in the ice-water bath, the reaction mixture was etracted with diethyl ether. The etheric solution was neutralized and dried and then evaporated to give the crude product (100%). This product was purified by crystallization from absolute diethyl ether. Yield= 47% m. p. 260C. TLC (I, 12: 2: 1). RF= 0,22. MS: 188,0 (100%, M-H+), 190,0 (65 %, M-H+)

The synthetic route of 130838-36-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INSTITUTE OF EXPERIMENTAL BOTANY ASCR; WO2004/18473; (2004); A2;,
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Synthetic Route of 22536-66-9, 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. 22536-66-9, name is 2-Chloropyrimidine-4-carboxamide. A new synthetic method of this compound is introduced below.

A tube containing a solution of 2-chloropyrimidine-4-carboxamide (0.24 g, 1 eq) and potassium(S)-trifluoro(3- ((3-hydroxy- 1 -methyl-2-oxopyrrolidin-3y1)ethynyl)phenyl)borate (1 eq) in Ethanol (0.25 M) was purged with nitrogen before addition of Pd(OAc)2 (0.06 eq), RuPhos (0.12 eq), and Sodium Carbonate (2 eq). The tube was sealed and stuffed at 85 C for 18 hours. The reaction mixture was cooled to room temperature and extracted with dichloromethane and saturated ammonium chloride then dried with Magnesium sulfate, filtered and concentrated todryness. The crude material subjected to reverse phase purification to afford 53 mg of the title compound (10%). M+H = 337.0; 1H NMR (400 MHz, DMSO-d6) oe 9.16-9.11 (m, 1H), 8.70- 8.60 (m, 3H), 7.98 (s, 1H), 7.94 (d, J = 5.0 Hz, 1H), 7.64 – 7.54 (m, 2H), 6.47 (s, 1H), 3.40 – 3.35 (m, 2H), 2.81 (s, 3H), 2.48 – 2.43 (m, 1H), 2.25 – 2.17 (m, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22536-66-9, 2-Chloropyrimidine-4-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; LIN, Xingyu; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25026; (2015); A1;,
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Synthetic Route of 302964-08-5 ,Some common heterocyclic compound, 302964-08-5, molecular formula is C16H13Cl2N5OS, 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.

Example 34; Procedure for the Preparation of Dasatinib Form N2A mixture of compound 1 (1.5 mmol), N-(2-hydroxyethyl)piperazine (3 mmol) and N-ethyldiisopropylamine (3 mmol) was heated in DMSO (1.3 ml) at 80-85 C. for 1.5 hours. n-Butanol (7.0 ml) was slowly added at this temperature. The suspension was slowly cooled to 0-5 C. Product was filtered off and washed with n-butanol (10.0 ml) and dried on the filter.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,302964-08-5, its application will become more common.

Reference:
Patent; SIMO, Ondrej; Filipcik, Jiri; Martaus, Alexandr; Jegorov, Alexandr; Gavenda, Ales; Aronhime, Judith; Vraspir, Pavel; Koltai, Tamas; Faustmann, Jiri; Gabriel, Roman; US2009/118297; (2009); A1;,
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Application of 1004-39-3, Adding some certain compound to certain chemical reactions, such as: 1004-39-3, name is 4,6-Diaminopyrimidine-2-thiol,molecular formula is C4H6N4S, 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 1004-39-3.

EXAMPLE 47 N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-4-(4,6-diamino-2-pyrimidinylthio)butyramide Following a procedure similar to that described in Example 34, but using N-[4-(4-piperidinomethyl-2-pyridyloxy) -cis-2-butenyl]-4-chlorobutyramide (prepared as described in Preparation 2) and 4,6-diamino-2-mercaptopyrimidine as starting materials, in relative proportions similar to those used in that Example, the title compound was obtained as an oil in a 48% yield. Nuclear Magnetic Resonance Spectrum (CDCl3), delta ppm: 1.39-1.50 (2H, multiplet); 1.55-1.67 (4H, multiplet); 1.83-2.14 (4H, multiplet); 2.30-2.47 (6H, multiplet); 3.10 (2H, triplet, J=6.8 Hz); 3.45 (2H, singlet); 3.99-4.09 (2H, multiplet); 4.61 (2H, broad singlet); 4.92 (2H, doublet, J=6.8 Hz); 5.24 (1H, singlet); 5.63-5.72 (1H, multiplet); 5.78-5.87 (1H, multiplet); 6.12-6.23 (1H, broad); 6.72-6.79 (1H, multiplet); 6.91 (1H, doublet, J=4.4 Hz); 8.05 (1H, doublet, J=4.4 Hz). Infrared Absorption Spectrum (CHCl3) numax cm-1: 2940, 1655, 1610, 1580, 1555, 1310.

According to the analysis of related databases, 1004-39-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sankyo Company, Limited; US5616579; (1997); A;,
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Electric Literature of 4318-56-3, 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. 4318-56-3, name is 6-Chloro-3-methylpyrimidine-2,4(1H,3H)-dione, molecular formula is C5H5ClN2O2, 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: 6-Chloropyrimidine-2,4(1H, 3H)-dione derivatives 1 (1.0 mmol) and N-hydroxyformimidoyl chloride derivatives 2 (1.2 mmol) were combined and dissolved in methanol (15mL), followed by the addition of triethylamine (3.0 mmol). Subsequently, the reaction mixture was stirred in a round-bottom flask (25mL) at room temperature for 5h. After completion of the reaction as indicated by TLC, the mixture was evaporated by rotary evaporator, extracted with ethyl acetate, dried over Na2SO4, then concentrated and purified by flash column chromatography (PE/EA=5:1) to yield compounds 3a-t.

According to the analysis of related databases, 4318-56-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jiang, Kun-Ming; Jin, Yi; Lin, Jun; Tetrahedron; vol. 73; 47; (2017); p. 6662 – 6668;,
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Electric Literature of 24415-66-5, Adding some certain compound to certain chemical reactions, such as: 24415-66-5, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine,molecular formula is C6H5ClN4, 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 24415-66-5.

General procedure: A mixture of 4 (50 mg; 0.296 mmol), Na2CO3 (60.74 mg; 0.592 mmol), Pd(PPh3)4 (34.66 mg; 0.030 mmol) and boronic acid (1.5 equiv.) was heated at 130 C in dioxane/water (4/1, 3 mL) for 3h. The reaction was followed by TLC. After completion, the mixture was filtered by celite and concentrated under vacuum. The solid obtained was submitted to a column chromatography. The increase of polarity in solvent gradient was made from neat petroleum ether to mixture of AcOEt/petroleum ether (6:4).

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. 24415-66-5, 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Loubidi, Mohammed; Moutardier, Anais; Campos, Joana F.; Berteina-Raboin, Sabine; Tetrahedron Letters; vol. 59; 11; (2018); p. 1050 – 1054;,
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Related Products of 147118-40-9, 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. 147118-40-9, name is Rosuvastatin methyl ester, molecular formula is C23H30FN3O6S, 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.

Example-5Preparation of Rosuvastatin Sodium Methyl 7-[4-(4-flourophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)- pyrimidin-5-yl]-(3R,5S)-dihydroxy -(E)–heptenate (100 g ) was added to ethyl alcohol (900 ml). To this aqueous sodium hydroxide (8.0 g sodium hydroxide dissolved in 500 ml of water) was added at a temperature of 0-5 °C. The reaction mixture was heated to room temperature and maintained for 1-2 hours. After completion of the reaction, the reaction mass was concentrated and ethyl alcohol was added and the reaction mass was distilled off azeotropically. To the obtained residue diisopropyl ether was added and stirred for lhour and filtered. The filtered solid was dried to yield Rosuvastatin sodium.

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 147118-40-9, Rosuvastatin methyl ester.

Reference:
Patent; MATRIX LABORATORIES LIMITED; WO2009/128091; (2009); A2;,
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Reference of 57005-71-7, 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 57005-71-7, name is 2-(4-Methylpiperazin-1-yl)pyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

A procedure similar to Example 59 (Method B), Parts A and B was used, except that 2-(4-methyl-1-piperazinyl)-4-pyrimidinamine (81 mg, 0.419 mmol) was used instead of 4-pyrimidinamine to add to the reaction mixture in Part A, to provide the Title compound. MS (ES+) m/z 489.2 (MH+). 1H NMR (400 MHz, METHANOL-d4) delta ppm 1.15 (dd, J=11.24, 7.20 Hz, 2H) 1.33-1.44 (m, 1H) 1.46-1.68 (m, 4H) 1.69-1.97 (m, 4H) 2.14-2.28 (m, 1H) 2.33 (s, 3H) 2.48 (t, J=5.05 Hz, 5H) 2.79-2.98 (m, 1H) 3.18-3.29 (m, 1H) 3.49 (dd, J=13.89, 4.55 Hz, 1H) 3.70-3.86 (m, 5H) 3.93 (tt, J=9.54, 4.86 Hz, 1H) 4.60-4.75 (m, 1H) 7.32 (d, J=5.56 Hz, 1H) 7.85 (s, 0.7H) 8.19 (d, J=5.56 Hz, 1H) 8.25 (s, 0.3H)

According to the analysis of related databases, 57005-71-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Glaxosmithkline LLC; Aubart, Kelly M.; Benowitz, Andrew B.; Fang, Yuhong; Hoffman, James; Karpinski, Joseph M.; Knox, Andrew Nicholson; Liao, Xiangmin; Qin, Donghui; Shi, Dongchuan; Spletstoser, Jared T.; US2013/345120; (2013); A1;; ; Patent; GlaxoSmithKline Intellectual Property (No. 2) Limited; Aubart, Kelly M.; Benowitz, Andrew B.; Fang, Yuhong; Hoffman, James; Karpinski, Joseph M.; Knox, Andrew Nicholson; Liao, Xiangmin; Qin, Donghui; Shi, Dongchuan; Spletstoser, Jared T.; US8901119; (2014); B2;,
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