Pyrimidines

Synthetic Route of 1753-50-0, 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. 1753-50-0, name is 2-Chloropyrimidine-5-carbonitrile. A new synthetic method of this compound is introduced below.

To a stirred solution of compound BO (0.55 g, 3.96 mmol) in EtOH (10 mL), 2-chloropyrimidine-5-carbonitrile (AF, 0.9 g, 3.96 mmol) and DIPEA (1.53 g, 11.9 mmol) were added at 80C and the reaction mixture was stirred at 90C for 12 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using 20% EtOAc/hexane to afford compound BP (0.5 g, 38.4 %) as a yellow oil; LC-MS: m/z 331.08 [M+H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1753-50-0, 2-Chloropyrimidine-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; VPS-3, INC.; YATES, Christopher, M.; (397 pag.)WO2018/165520; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 147118-39-6 ,Some common heterocyclic compound, 147118-39-6, molecular formula is C23H28FN3O6S, 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.

In a round bottom flask 2000 ml Tetrahydrofuran (THF) was added under the nitrogen atmosphere and cooled to -90°C then 1Og sodium borohydride was added followed by 230ml diethylmethoxyborane (1 M solution in THF) in 90-120mins. In this reaction mass, mixture of lOOg of Methyl -7-[4-(4-fiourophenyl)-6-isopropyl-2-(N-methyl-N- methylsulfonylaniino)-pyrimidin-5-yl]-(3R)-3-hydroxy-5-oxo-(E)-6-heptenate5 700 ml THF and 700 ml methanol was added for a duration of 90-120min then stirred for 2 hrs at -90 to -80°C. After the completion of reaction, 124 ml acetic acid was added and stirred for 30-60 min at same temperature. Above reaction mass was diluted with 1500ml ethyl acetate and washed with brine solution. To the organic layer, 500 ml DM water was added and pH was adjusted to neutral by ~ 500 ml 6 percent sodium bicarbonate solution. Both the layers were separated Sc the organic layer was dried over sodium sulphate. The organic layer was concentrated at 40-450C. Above concentrated mass was diluted with 900ml ethyl alcohol and then cooled to 0°C. Sodium hydroxide solution was added in 60- 90 min. The reaction mass was stirred for 30 min at room temperature and the pH was adjusted to 11.5-12.0 by using ~ 4 percent sodium hydroxide solution. In this reaction mass, 1Og activated carbon was added and stirred for 20 min. The reaction mass was filtered and washed with ethanol/DM water mixture. The reaction mass was concentrated up to thick residue at 40-45°C. To this concentrated mass, 500 ml DM water was added followed by 1000ml ethyl acetate and the pH was adjusted to 3.5- 4.0 with 1:4 aqueous hydrochloric acid. Both the layers were separated and the organic layer was washed with brine solution.The organic layer was dried over sodium sulphate and concentrated till dryness at 40-45°C. To the above concentrated mass, 1000 ml acetonitrile was added stirred at room temperature for half an hour. Slowly 20.5 g (S)-2-amino-3, 3 -dimethyl butane was added and stirred for almost 2 hrs. The solid was filtered and washed with acetonitrile and diisopropyl ether. Finally the solid was dried for 6-9 hrs at 40-45°C.Above obtained (S)-2-amino-3, 3 -dimethyl butane salt of rosuvastatin was suspended in 1000 ml isopropanol followed by 100 ml methanol. This reaction mass was heated for half an hour at 60-80°C then stirred for 3-4 hrs at 5-1O0C. The solid was filtered washed with isopropanol and diisopropyl ether. 95 gms of (S)-2-amino-3, 3 -dimethyl butane salt of rosuvastatin was obtained.

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. 147118-39-6, 5-Oxorosuvastatin methyl ester, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MATRIX LABORATORIES LTD; SETHI, Madhuresh, Kumar; MAHAJAN, Sanjay; MARA, Bhairaiah; AYYARAN, Laxmi, Karthikeyan; DATTA, Debashish; WO2010/35284; (2010); A2;,
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.24415-66-5, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, molecular formula is C6H5ClN4, molecular weight is 168.58, as common compound, the synthetic route is as follows.Quality Control of 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine

The preparation method of the compound e18 comprises the steps of: taking about 1 mmol of 7-chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine and about 3 mmol.1-(2,4-Dichlorobenzyl)-1H-indole was added to a 10 mL microwave reaction tube.Further, 2 mL of hexafluoroisopropanol solvent and about 0.1 mmol of bistrifluoromethanesulfonimide catalyst were added, sealed and heated to 100 C with stirring and reacted for about 6 h.Then, the reaction system was monitored by TLC, and after the reaction system was cooled to room temperature, it was separated and purified by column chromatography to obtain pure compound e18.The compound e18 is a brown solid with a yield of 85%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,24415-66-5, 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Zhengzhou University; Liu Hongmin; Yu Bin; Zheng Yichao; Yuan Shuo; Shen Dandan; (27 pag.)CN109020976; (2018); A;,
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Pyrimidine – Wikipedia

Synthetic Route of 54660-78-5 ,Some common heterocyclic compound, 54660-78-5, molecular formula is C4H4ClN3, 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.

(1) Synthesis of tert-butyl 3-((5-aminopyrimidin-4-yl)oxy)pyrrolidine-1-carboxylate (1D3) At room temperature, NaH (71 mg, 2.94 mmol) was added to a solution of tert-butyl-3-hydroxypyrrolidine-1-carboxylate (1B2) (500 mg, 2.67 mmol) in THF (tetrahydrofuran) (10 mL) and stirred for 1 hour. 4-chloropyrimidin-5-amine (H) (348 mg, 2.67 mmol) was then added. The reaction mixture was then heated to 100° C. under nitrogen and stirred for 4 hours, cooled to room temperature (20-30° C.) and concentrated in vacuo. The residue was purified with flash column (eluent: 10-30percent ethyl acetate/petroleum ether) to obtain the product 1D3 (336 mg, 1.2 mmol).

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. 54660-78-5, 4-Chloropyrimidin-5-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Jikai Biosciences, Inc.; GE, Yu; US2014/162999; (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. 10132-07-7, name is 4-Amino-2,6-dichloropyrimidine, molecular formula is C4H3Cl2N3, 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. Recommanded Product: 4-Amino-2,6-dichloropyrimidine

2,6-Dichloro-pyrimidin-4-ylamine and 3-bromo-2-oxo-propionic acid ethyl ester were reacted to provide 5,7-dichloro-imidazo[1,2-c]pyrimidine-2-carboxylic acid ethyl ester. The title compound was prepared from 5,7-dichloro-imidazo[1,2-c]pyrimidine-2-carboxylic acid ethyl ester and 5-methyl-1H-pyrazol-3-ylamine according to the procedure described in Scheme 7. 1H NMR (400 MHz, DMSO) 10.81 (s, 1H) 9.10 (s, 1H) 7.10 (s, 1H) 6.48 (s, 1H) 4.37 (q, J=7.2 Hz 2H) 2.28 (s, 3H) 1.33 (t, J=7.2 Hz, 3H). [M+H] calc’d for C13H14ClN6O2, 321; found, 321.

With the rapid development of chemical substances, we look forward to future research findings about 10132-07-7.

Reference:
Patent; Dong, Qing; Hosfield, David J.; Paraselli, Bheema R.; Scorah, Nicholas; Stafford, Jeffrey A.; Wallace, Michael B.; Zhang, Zhiyuan; US2006/84650; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1032452-86-0, 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.1032452-86-0, name is 3-(2-Chloropyrimidin-4-yl)-1-methyl-1H-indole, molecular formula is C13H10ClN3, molecular weight is 243.69, as common compound, the synthetic route is as follows.

4-Methylbenzenesulfonic acid hydrate (8.7 g) was added in one portion to 3-(2- chloropyrimidin-4-yl)-1-methylindole (9.3 g) and 4-fluoro-2-methoxy-5-nitroaniline (7.1 g) in nbutanol (200 mL). The resulting mixture was stirred at reflux for 1 h. The mixture was cooled to room temperature. The precipitate was collected by filtration, washed with n-butanol (50 mL), and dried under vacuum to afford N-(4-fluoro-2-methoxy-5-nitrophenyl)- 4-(1- methylindol-3- yl)pyrimidin-2-amine as a yellow solid (CompoundS, 15.5 g).

Statistics shows that 1032452-86-0 is playing an increasingly important role. we look forward to future research findings about 3-(2-Chloropyrimidin-4-yl)-1-methyl-1H-indole.

Reference:
Patent; NEUFORM PHARMACEUTICALS, INC.; CHAORAN, Huang; CHANGFU, Cheng; (85 pag.)WO2017/117070; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1004-17-7, 2-Methylpyrimidine-4-carbaldehyde, 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, 1004-17-7, blongs to pyrimidines compound. Product Details of 1004-17-7

Step A 3-(2-Methyl-pyrimidin-5-yl)-propenal (2-2) To a solution of 4-formyl-2-methylpyrimidine [2-1, 2 g, 16.4 mmol; for preparation, see Smith, S. Q. et al, J. Heterocyclic Chem. 28: 1281 (1991)] in methylene chloride (15 mL) was added (formylmethylene)triphenylphosphorane (5.98g, 19.6 mmol). The solution was heated at reflux for 4 h, cooled to room temperature, and solvents evaporated. The residue was chromatographed on silica gel (30% EtOAc/chloroform to 50 EtOAc/50 chloroform/5 methanol) to give the aldehyde 2-2 as a yellow solid. TLC Rf=0.39 (70 chloroform/25 EtOAc/5 MeOH). 1H NMR (400 MHz, CDCl3) delta 9.74 (d, 1H, J=7 Hz), 8.83 (s, 2H), 7.41 (d, 1H, J=7 Hz), 6.81 (dd, 1H, S=6 Hz, 15 Hz), 2.77 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1004-17-7, its application will become more common.

Reference:
Patent; Merck & Co., Inc.; US6410526; (2002); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1224944-77-7 ,Some common heterocyclic compound, 1224944-77-7, molecular formula is C9H8ClN3O2, 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.

A mixture of ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate (677 mg, 3.00 mmol), Nmethylmethanamine hydrochloride (489 mg, 6.00 mmol) and N,N-diisopropylethylamine (1 .6 ml, 9.0 mmol) in 2-propanol (20 ml) was refluxed for 5 h. Upon cooling, ice water was added and the mixture was extracted with ethyl acetate (3x). The combined organic phases were filtrated through a silicone filter and concentrated to give the title compound (674 mg).[C-MS (Method 1): R = 0.84 mm; MS (ESIpos): m/z = 235 [M+H]1H-NMR (400 MHz, DMSO-d6) 6 [ppm]: 1.261 (7.26), 1.278 (16.00), 1.296 (7.57), 3.182(14.34), 4.157 (2.25), 4.175 (7.19), 4.193 (7.07), 4.211 (2.14), 6.691 (4.60), 6.710 (4.61),8.181 (9.13), 8.673 (5.48), 8.693 (5.36).

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. 1224944-77-7, Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (2016); 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. 878742-59-7, name is 2-(Trifluoromethyl)pyrimidine-4-carboxylic acid, molecular formula is C6H3F3N2O2, 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. Application In Synthesis of 2-(Trifluoromethyl)pyrimidine-4-carboxylic acid

To a solution of {1-[cis-3-fluoropiperidin-4-yl]-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile (200 mg, 0.4 mmol) and 2-(trifluoromethyl)pyrimidine-4-carboxylic acid (83 mg, 0.43 mmol) in DMF (10 mL) were added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (5.20E2 mg, 1.17 mmol) and triethylamine (0.14 mL, 0.98 mmol). The mixture was stirred at room temperature overnight and purified with prep-LCMS to give 100 mg (36% yield) of the desired compound as a white solid.

With the rapid development of chemical substances, we look forward to future research findings about 878742-59-7.

Reference:
Patent; Huang, Taisheng; Xue, Chu-Biao; Wang, Anlai; Kong, Ling Quan; Ye, Hai Fen; Yao, Wenqing; Rodgers, James D.; Shepard, Stacey; Wang, Haisheng; Shao, Lixin; Li, Hui-Yin; Li, Qun; US2011/224190; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 56181-39-6, Adding some certain compound to certain chemical reactions, such as: 56181-39-6, name is 5-Bromo-4-chloropyrimidine,molecular formula is C4H2BrClN2, 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 56181-39-6.

EXAMPLE 13: 5-bromo-N-(l-methylpiperidin-4-yl)pyridine-4-amine17To a stirred solution of 5-bromo-4-chloropyrimidine (300mg, 1.562mmol) in DMF, DIPEA (400mg, 3.124mmol) was added followed by l-methylpiperidine-4-amine (0.193ml, 1.562mmol) and the reaction mixture was heated at 80 C overnight. TLC showed absence SM, and then reaction mixture was concentrated. The crude product was purified by flash column chromatography over 230-400 mesh silica gel and using a mixture of 30% EtO Ac/petroleum ether to afford the desired product 17, 180mg (Yield: 40 %) as yellow solid. The product was confirmed by 1FiNMR and MS spectrum analysis. 1H NMR (400 MHz, CDC13) delta: 8.4 (s, 1H), 8.35 (s, 1H), 6.81 (d, 1H), 4.95 (m, 1H), 2.78 (d, 2H), 2.17 (s, 3H), 1.95 (t, 2H), 1.6-1.8 (m, 4H); MS- 270 (M+l).

According to the analysis of related databases, 56181-39-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARRIEN PHARMAEUTICALS LLC; VANKAYALAPATI, Hariprasad; APPALANENI, Rajendra, P.; REDDY, Y., Venkata Krishna; WO2012/135631; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia