Pyrimidines

Reference of 213265-83-9, 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. 213265-83-9, name is 4,6-Dichloro-5-fluoropyrimidine, molecular formula is C4HCl2FN2, 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.

tert-butyl 4-[(2-{[6-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-benzim idazol-2-yl]am ino}pyridin-4-yl)methyl]piperazine-1 -carboxylate (500 mg, see Compound 01.04), 4,6- dichloro-5-fluoropyrimidine (469 mg), aqueous Na2CO3 (1.4 ml, 2.0 M) and 1,1?- bis(diphenylphosphino)ferrocene-palladium(I I )dichloride dichloromethane complex (76.4 mg) were stirred in a sealed tube in a mixture of 1,4-dioxane (10 ml) and water (2.0 ml) overnight at110?C. The mixture was then filtered over a silicone filter and concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica gel to give 556 mg (60 % purity) of the title compound.LC-MS (method 2): R = 1.36 mm; MS (ESlpos): m/z = 537 [M-H]1H..NMR (400 MHz, DMSO-d6) O [ppm]: 1.065 (16.00), 1.155 (1.74), 1.299 (1.42), 1.393 (2.88),1.414 (1.32), 2.539 (0.70), 3.334 (0.76), 3.937 (0.68), 8.097 (0.85).

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 213265-83-9, 4,6-Dichloro-5-fluoropyrimidine.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; HEINRICH, Tobias; PRINZ, Florian; LEFRANC, Julien; SCHROeDER, Jens; MENGEL, Anne; BONE, Wilhelm; BALINT, Joszef; WENGNER, Antje; EIS, Knut; IRLBACHER, Horst; KOPPITZ, Marcus; BOeMER, Ulf; BADER, Benjamin; BRIEM, Hans; LIENAU, Philip; CHRIST, Clara; STOeCKIGT, Detlef; HILLIG, Roman; (1256 pag.)WO2017/102091; (2017); A1;,
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Reference of 5413-85-4, 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 5413-85-4 as follows.

EXAMPLE 13; 6-r4-(Aminophenylmethyl)piperidin-1-yll-7,9-dihydropurin-8-one; 13A. 5,6-Diamino-4-chloropyrimidine; A mixture of 4,6-dichloro-5-aminopyrimidine (Aldrich Chemical Co.) (2.0 g, 12.2 mmol) and concentrated aqueous ammonia (20 ml) was heated to 100 0C in a sealed glass tube with vigorous stirring for 18 hours. The cooled tube was recharged with concentrated aqueous ammonia (8 ml), aggregates were broken up, and the mixture was reheated at 100 0C for a further 28 hours. The mixture was evaporated to dryness and the solids were washed with water (20 ml) and dried to give the product as yellow crystals (1.71 g, 97%). LC/MS (LCT1): R, 1.59 [M+H]+ 147, 145.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5413-85-4, its application will become more common.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; THE INSTITUTE OF CANCER RESEARCH:ROYAL CANCER HOSPITAL; CANCER RESEARCH TECHNOLOGY LIMITED; WO2007/125315; (2007); A2;,
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Synthetic Route of 2915-16-4 , The common heterocyclic compound, 2915-16-4, name is 2-Chloro-4,6-diphenylpyrimidine, molecular formula is C16H11ClN2, 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.

After introducing compound 4-1 (5.2 g, 12.3 mmol),2-chloro-4,6-diphenylpyrimidine (CAS: 2915-16-4, 3.3 g, 12.3 mmol), tetrakis(triphenylphosphine)palladium (0.71 g, 0.62 mmol), potassium carbonate (4.2 g, 30 mmol), toluene (60 mL), ethanol (20 mL), and distilled water (20 mL) into a reaction vessel, the mixture was stirred for 4 hours at 120C. After completing the reaction, the mixture was added dropwise to methanol, and the obtained solid was filtered. The obtained solid was purified by column chromatography and recrystallization to obtain compound C-75 (5.3 g, 82 %).

The synthetic route of 2915-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.; AHN, Hee-Choon; (41 pag.)WO2017/30283; (2017); A1;,
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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. 73-70-1, name is 2,5-Dimethylpyrimidin-4-amine. A new synthetic method of this compound is introduced below., SDS of cas: 73-70-1

a. 3-Amino-2,5-dimethylpyrimidin-4(3H)-iminium-2,4,6-trimethylbenzenesulfonate A mixture of 2,5-dimethylpyrimidin-4-amine (15.2 g, 49.0 mmol) in DCM (30 mL) was stirred at room temperature, and O-(mesitylsulfonyl)hydroxylamine (2.0 g, 16.0 mmol) was added slowly. The reaction mixture was stirred at room temperature for 12 h, then the solvent was removed under reduced pressure. The crude product was used for the next step without further purification. ESI MS: m/z 139 [M+H]+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 73-70-1, 2,5-Dimethylpyrimidin-4-amine.

Reference:
Patent; Sunovion Pharmaceuticals Inc.; US2012/178748; (2012); A1;,
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Related Products of 2227-98-7, 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. 2227-98-7, name is 4-Aminopyrrolo[3,2-d]pyrimidine, molecular formula is C6H6N4, 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.

[0075] (3R,4S)-l-({4-Amino-5R^yrrolof3,2-dJpyrimidin-7-yl}methyl)-4-f(pyridin-2- ylthio)methyl]pyrrolidin-3-ol (24). Compound 23 (0.171 g, 0.55 mmol) was dissolved in MeOH (4 mL) and aq. hydrochloric acid (36%, 1.5 mL) added. After 15 min the solvent was evaporated to yield a colourless gum that was dissolved in MeOH (10 mL), neutralized with Amberlyst A21 resin then passed through a short column of the same resin eluted with MeOH. The solvent was evaporated and the residue dissolved in a mixture of EtOH (4 mL) and H20 (2 mL) to which were added aq. formaldehyde solution (37%, 0.08 mL, 1 mmol) and 9-deazaadenine (0.096 g, 0.72 mmol). The mixture was heated at 70 C for 16 h and silica gel was added to absorb all the solvent then the solvent was evaporated and the residue purified by chromatography on silica gel (gradient of 0 – 7% aq. NH4OH (28%) in 2-PrOH). The fractions containing product were evaporated and the residue further chromatographed on silica gel (CHC13-7M NH3/MeOH, 85: 15) to afford 24 as a colourless solid (0.087 g, 44%). XH NMR (500 MHz, 1 : 1 CD30D-CDC13): delta 8.34 (ddd, J = 5.0. 1.8, 0.9 Hz, 1H), 8.19 (s, 1H), 7.54 (ddd, J = 9.7, 7.7, 1.9 Hz, 1H), 7.41 (s, 1H), 7.23 (dt, J = 8.2, 0.9 Hz, 1H), 7.03 (ddd, J= 7.3, 5.0, 0.9 Hz, 1H), 4.07 (ddd, J= 6.4, 3.9, 3.9 Hz, 1H), 3.85 (d, J= 13.5 Hz, 1H), 3.81 (d, J= 13.4 Hz, 1H), 3.37-3.34 (m, 1H + residual deuterated solvent), 3.15 (dd, J= 13.1, 8.2 Hz, 1H), 3.10-3.06 (m, 1H), 2.87 (dd, J = 10.4, 6.4 Hz, 1H), 2.74 (dd, J = 10.4, 3.9 Hz, 1H), 2.41-2.33 (m, 2H). 13C NMR (125.7 MHz, 1 : 1 CD3OD-CDC centre lines delta 49.0 and delta 78.3): delta 159.8 (C), 151.2 (C), 150.4 (CH), 149.7 (CH), 146.5 (C), 137.2 (CH), 129.1 (CH), 123.0 (CH), 120.4 (CH), 1 14.7 (C), 1 12.2 (C), 76.3 (CH), 61.9 (CH2), 58.4 (CH2), 48.7 (CH2), 47.9 (CH), 33.5 (CH2). ESI-HRMS calcd for Ci7H21N6OS+, (M+H)+, 357.1493, found 357.1485.

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 2227-98-7, 4-Aminopyrrolo[3,2-d]pyrimidine.

Reference:
Patent; ALBERT EINSTEIN COLLEGE OF MEDICINE OF YESHIVA UNIVERSITY; CALLAGHAN INNOVATION RESEARCH LIMITED; SCHRAMM, Vern, L.; WANG, Shanzhi; HAAPALAINEN, Antti, Marko; EVANS, Gary, Brian; FURNEAUX, Richard, Hubert; CLINCH, Keith; TYLER, Peter, Charles; GULAB, Shivali, Ashwin; WO2014/25842; (2014); A1;,
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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. 58536-46-2, name is 4-(4-Bromophenyl)-2,6-diphenylpyrimidine. A new synthetic method of this compound is introduced below., category: pyrimidines

Under an Ar gas atmosphere, the intermediate body X3 (4.8 g, 10 mmol), the intermediate body X7 (3.9 g, 10 mmol), an aqueous solution of 2M sodium carbonate (12 ml), toluene (20 ml), DME (20 ml) and Pd(PPh3)4 (0.35g) were stirred for 16 hours at a reflux temperature. After the reactant solution was cooled down to the room temperature, toluene (200 ml) and water (100 ml) were added thereto to separate an organic phase. The residue obtained by concentrating the organic phase was refined by silica-gel column chromatography (a developing solvent: hexane-toluene) and was recrystallized by toluene twice to provide a target object (a compound No. 4) as a white solid. A yield of the compound No. 4 was 2.6 g and a yield rate thereof was 35%. FD mass analysis consequently showed that m/e was equal to 741 while a calculated molecular weight was 741

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 58536-46-2, 4-(4-Bromophenyl)-2,6-diphenylpyrimidine.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; EP2489664; (2012); A1;,
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Related Products of 941685-26-3 , The common heterocyclic compound, 941685-26-3, name is 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C12H18ClN3OSi, 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.

Step 1: (3aS,7aS and 3aR,7aR) tert-butyl 4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)octahydro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate To a stirred solution of Intermediate 2a (0.700 g, 2.47 mmol) and (3aS,7aS and 3aR,7aR) tert-butyl octahydro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate (HOAc salt; 0.918 g, 3.21 mmol; Intermediate 1a process, Step 4) in DMF (14 mL) was added TEA (1.03 mL, 7.40 mmol). The resulting reaction mixture was stirred at 90 C overnight. The reaction mixture was partitioned between EtOAc and 10% aqueous sodium chloride and the organic layer was washed with additional 10% aqueous sodium chloride. The first aqueous layer was extracted with additional EtOAc and the combined organic washings were dried over sodium sulfate and filtered. Silica gel was added to the filtrate and the mixture was concentrated in vacuo to a crude solid. The resulting solid was purified by column chromatography on silica gel, eluting with EtOAc/hexane (12-100%) to afford the desired product. LRMS calc’d for C24H40N5O3Si [M+H]+, 474; found 474. 1H NMR (500 MHz, DMSO-D6) delta 8.20 (s, 1H), 7.35 (d, 1H), 6.69 (d, 1H), 5.50 (s, 2H), 5.13 (br m, 1H), 4.59 (br d, 1H), 3.80-3.68 (br m, 1H), 3.47 (t, 2H), 3.41-3.32 (br m, 2H), 3.05 (br t, 1H), 2.09 (br m, 2H), 1.99 (br m, 1H), 1.75 (br m, 1H), 1.39 (overlapping s, m, 11H), 0.80 (t, 2H), -0.10 (s, 9H).

The synthetic route of 941685-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; GUERIN, David Joseph; BRUBAKER, Jason, D.; MARTINEZ, Michelle; JUNG, Joon, O.; ANTHONY, Neville, J.; SCOTT, Mark, E.; HOFFMAN, Dawn Marie Mampreian; WOO, Hyun Chong; DINSMORE, Christopher, J.; (75 pag.)EP2629777; (2018); B1;,
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Synthetic Route of 330794-31-5, 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 330794-31-5, name is 1-Cyclopentyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

Example 92 3-[3-(Benzyloxy)phenyl]-1-cyclopentyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine To a mixture of 1-cyclopentyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.200 g, 0.631 mmol, 1 equiv) and 3-(benzyloxy)phenylboronic acid (0.110 g, 0.487 mmol, 1.0 equiv) in DME (6 mL) was added tetrakis(triphenylphosphine)palladium (0.044 g, 0.038 mmol, 0.07 equiv) and a solution of sodium carbonate monohydrate (0.187 g, 1.51 mmol, 2.4 equiv) in water (2 mL). The mixture was heated at 85 C. for 16 h, then allowed to cool to ambient temperature. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc (50 mL) and water (50 mL). The organic layer was dried over MgSO4, filtered, and concentrated to afford an oily red-orange solid. Recrystallization from hot EtOAc afforded a red-orange solid which was purified by preparative RP-HPLC (Rainin C18, 8 mum, 300 A, 25 cm; 10%-60% acetonitrile-0.1M ammonium acetate over 20 min, 21 mL/min). The acetonitrile was removed in vacuo and the aqueous mixture was lyopholyzed to afford 3-[3-(benzyloxy)phenyl]-1-cyclopentyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine as a whitesolid (0.023 g, 0.060 mmol): 1H NMR (d6 CDCl3, 400 MHz): deltaH 8.34 (1H, s), 7.27-7.46 (8H, m), 7.07-7.10 (1H, m), 5.63 (2H, bs), 5.31 (1H, quint, J=7.6 Hz), 5.16 (2H, s), 2.15-2.20 (4H, m), 1.96-2.01 (2H, m), 1.72-1.75 (2H, m); RP-HPLC (Hypercil C18, 5 mum, 100 A, 15 cm; 5%-100% acetonitrile-0.1M ammonium acetate over 15 min, 1 mL/min) Rt 14.00 min. MS: MH+ 386.

According to the analysis of related databases, 330794-31-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Abbott Laboratories; US2002/156081; (2002); A1;,
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Application of 1211443-61-6, 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.1211443-61-6, name is 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide, molecular formula is C14H17ClN4O, molecular weight is 292.76, as common compound, the synthetic route is as follows.

A mixture of /erf-butyl 4-(6-aminopyridin-3-yl-2,4,5-d3)piperazine-l-carboxylate (600 mg, 2.1 mmol) and 2-chloro-7Patent; LI, George, Y.; HOU, Duanjie; (43 pag.)WO2018/81211; (2018); A1;,
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Reference of 213265-83-9, Adding some certain compound to certain chemical reactions, such as: 213265-83-9, name is 4,6-Dichloro-5-fluoropyrimidine,molecular formula is C4HCl2FN2, 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 213265-83-9.

0.58 g of sodium hydride (60% oil suspention) was suspended in 20 ml of tetrahydrofuran. 1 ml of tetrahydrofuran solution of 0. 88 g of 2-PENTYN-1-OL was added dropwise at 0C therein slowly, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 5 ml of tetrahydrofuran solution of 2 g of 4,6-dichloro-5-fluoropyrimidine at 0C, and stirred for 70 minutes. The reaction mixture was poured into a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 2.31 g of 4-CHLORO-5-FLUORO-6- (2-PENTYNYLOXY) pyrimidine. LH-NMR : 1.15 (t, 3H), 2.24 (qt, 2H), 5.09 (t, 2H), 8.36 (s, 1H)

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. 213265-83-9, 4,6-Dichloro-5-fluoropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2004/99160; (2004); A1;,
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Pyrimidine – Wikipedia