Pyrimidines

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. 51940-64-8, name is Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate, molecular formula is C7H6Cl2N2O2, 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 Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate

DIPEA (8.76 mL, 50.31 mmol) was added dropwise to a mixture of (ls,4s)-4-amino-1-methylcyclohexan-1-ol (5.00 g, 38.70 mmol) and ethyl2,4-dichloropyrimidine-5-carboxylate (8.55g, 38.70 mmol) in acetonitrile (143 mL) at -5C over a period of 15 min under air. The reaction5 mixture was stirred for 2 h, then was slowly allowed to warm tort, concentrated in vacuo, dilutedwith EtOAc (200 mL), and washed with water then with sat. brine. The organic layer was driedover MgS04, filtered and concentrated in vacuo. The resulting crude mixture was suspended inDCM (20 mL ), and the resulting solid was isolated by filtration and was washed with DCM ( 5 mL)to afford title compound (3.8 g). The filtrate was purified by fcc, elution gradient 0 to 70% EtOAc10 inn-heptane, to afford additional title compound (5.3 g). Both batches were combined to afford thetitle compound (9.10 g, 75%) as a white solid; 1H NMR (400 MHz, DMSO) 1.13 (3H, s), 1.32 (3H,t), 1.43 (2H, td), 1.53 – 1.61 (2H, m), 1.69 (4H, tt), 3.85- 3.99 (lH, m), 4.15 (lH, s), 4.32 (2H, q),8.27 (lH, d), 8.62 (lH, s); m/zMH+ 314.

With the rapid development of chemical substances, we look forward to future research findings about 51940-64-8.

Reference:
Patent; ASTRAZENECA AB; CANCER RESEARCH TECHNOLOGY LIMITED; FINLAY, Maurice, Raymond, Verschoyle; GOLDBERG, Frederick, Woolf; HOWARD, Martin, Richard; TING, Attilla, Kuan, Tsuei; (145 pag.)WO2019/238929; (2019); A1;,
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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 5305-45-3, name is 4,6-Dichloropyrimidine-5-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 5305-45-3

To a mixture of 22a (55 mg, 0.2 mmol) in THF (2 mL) was added NaH (16 mg 0.4 mmol) at 0 C, the mixture was stirred at 0 C for 30 min, then 4,6-dichloropyrimidine-5- carbonitrile (42 mg 0.24 mmol) was added, the reaction was stirred at 0 C- r.t for 2 h. The mixture was quenched by MeOH, concentrated and purified by flash column chromatography to give 22b as a yellow solid (50 mg, yield: 60%). MS (m/z): 412.9 (M+l)+.

With the rapid development of chemical substances, we look forward to future research findings about 5305-45-3.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; DAI, Guangxiu; XIAO, Kun; JIA, Hong; VENABLE, Jennifer Diane; BEMBENEK, Scott Damian; WO2014/15523; (2014); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 2915-16-4, name is 2-Chloro-4,6-diphenylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. name: 2-Chloro-4,6-diphenylpyrimidine

To a 1 L flask was placed 11- (3- (dibenzo [b, d] furan-4-yl) phenyl) – 11,12-dihydroindolo [2,3- a] – carbazole (20 g), sodium hydride 4.8 g) and toluene (300 ml), and the mixture was stirred at 40 C. under a nitrogen atmosphere. After 1 hour, 2-chloro-4,6-diphenyl-1,3-pyrimidine (12.8 g) was added and stirring was continued at 80 F.The reaction was monitored by thin layer chromatography. After the reaction was completed, the reaction mixture was quenched with water (200 ml) and extracted using ethyl acetate (150 ml). The organic layer was extracted with water (3 ¡Á 100 ml) and dried over anhydrous sodium sulfate. For further purification, the collected ethyl acetate layer was passed through Celite column chromatography. Subsequently, the ethyl acetate layer was evaporated and dried under reduced pressure using a rotary evaporator. 100 ml of n-hexane was added, filtrated, and reduced pressure The residue was further precipitated by drying. As a yellow solid, 18 g (85%) of Compound F5 having an HPLC purity of 99% or more was obtained.

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, 2915-16-4, 2-Chloro-4,6-diphenylpyrimidine.

Reference:
Patent; E-RAY OPTOELECTRONICS TECHNOLOGY COMPANY LIMITED; BALAGANESAN, BANUMATHY; HUANG, HEHLUNG; GUO, HUNG MING; HSU, POWEI; (23 pag.)JP2017/31112; (2017); A;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 33034-67-2, name is 2-Chloro-4-(trifluoromethyl)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 2-Chloro-4-(trifluoromethyl)pyrimidine

Step C. 7-(4-Trifluoromethyl-pyrimidin-2-yl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-ol. A solution of 6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-ol (60 mg, 0.30 mmol), 2-chloro-4-tritrifluoropyrimidine (36 muL, 0.30 mmol), and Et3N (0.11 mL, 0.81 mmol) in DMF (1.2 mL) was heated at 120¡ã C. for 2 h. The mixture was cooled to rt, diluted with water, and extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated to give the title compound (69 mg, 68percent), which was used without further purification.

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, 33034-67-2, 2-Chloro-4-(trifluoromethyl)pyrimidine.

Reference:
Patent; Allison, Brett D.; Branstetter, Bryan James; Breitenbucher, James Guy; Hack, Michael D.; Hawryluk, Natalie A.; Lebsack, Alec D.; McClure, Kelly J.; Merit, Jeffrey E.; US2007/225275; (2007); A1;,
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Electric Literature of 13162-27-1, Adding some certain compound to certain chemical reactions, such as: 13162-27-1, name is 2,4-Dichloro-6-methylpyrimidin-5-amine,molecular formula is C5H5Cl2N3, 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 13162-27-1.

The raw material 14 (2.63g), adding 263mg of Pd / C, adding triethylamine 3.5ml, anhydrous ethanol 88ml, water 4ml, 20psi hydrogen pressure reaction 8h, the raw material reaction is complete after the filter, spin dry solvent, Yellow solid, dry loading, purification to obtain white solid 15 (1.22g) yield 74.4%.

According to the analysis of related databases, 13162-27-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SICHUAN BAILI PHARMACEUTICAL CO LTD; WU, YONG; ZHU, YI; HAI, LI; WANG, YIXI; LI, JIE; (23 pag.)CN105906621; (2016); A;,
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Reference of 52606-02-7 ,Some common heterocyclic compound, 52606-02-7, molecular formula is C7H8N2O3, 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 10 rac-5-[(4S*,5R*)-4,5-Bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-1 H-imidazol-2-yl]-2,4-dimethoxy-pyhmidineThe title compound was prepared using the procedure described by Ishihara, M. and Togo, H. Synlett 2006, 2, 227-230 and ibid Tetrahedron 2007, 63, 1474- 1480.Iodine (172 mg, 0.68 mg) was dissolved in tert-butanol (20 ml_) and potassium carbonate (300 mg, 2.2 mmol) was added. 2,4-Dimethoxy-5-formylpyhmidine (100 mg, 0.6 mmol, Frontier) and (rac)-2,3-Bis(4-chloro-phenyl)-butane-2,3- diamine (200 mg, 0.65 mmol) was added to the mixture. This was warmed to 65 0C for 2 h. This was cooled, diluted with ethyl ether (50 ml_) and filtered through CeI ite. After evaporating to dryness, the residue was purified by flash column chromatography (silica gel, eluting with 2-5% methanol/methylene chloride) to give rac-5-[(4S*,5R*)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5- dihydro-1 H-imidazol-2-yl]-2,4-dimethoxy-pyrimidine.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,52606-02-7, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2009/47161; (2009); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1192479-35-8, name is 2-Chloro-5-fluoro-4-methoxy-6-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 2-Chloro-5-fluoro-4-methoxy-6-methylpyrimidine

To a solution of 2-chloro-5-fluoro-4-methoxy-6-methylpyrimidine (2 g) in carbon tetrachloride (24 ml) was added AIBN (0.2 g) and NBS (6 g) and the reaction mixture stirred under reflux for twenty six hours then allowed to cool overnight. The reaction mixture was poured into cold water and extracted with dichloromethane (2 x 100 ml); the combined organic layer was washed with water and brine then dried (MgSC”4) and evaporated. The residue was triturated with diethyl ether / hexane and a white solid filtered off and the filtrate evaporated to give the title compound (2.61 g) which contained an approximately 1 :3 mixture of 4-(bromomethyl)-2-chloro-5-fluoro-6- methoxypyrimidine : 2-chloro-5-fluoro-4-methoxy-6-methylpyrimidine.

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, 1192479-35-8, 2-Chloro-5-fluoro-4-methoxy-6-methylpyrimidine.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; HALL, Adrian; FARTHING, Christopher Neil; EATHERTON, Andrew John; WO2014/13076; (2014); A1;,
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Application of 705263-10-1, 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 705263-10-1 as follows.

Preparative Example 14 Step 1 : 6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyrazolo[l,5-a]pyrimidine To a solution of 6-bromopyrazolo[l,5-a]pyrimidine (1.5 g, 7.57 mmol) in 1,4-dioxane (20 mL) were added 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (2.12 g, 8.33 mmol), potassium acetate (1.48 g, 15.14 mmol) and l,l’-bis(diphenylphosphino)ferrocene-palladium(II)dichloride (553 mg, 0.76 mmol). The reaction mixture was purged with nitrogen for 2 min and heated to 100 C for 4 h and subsequently concentrated to dryness in vacuo. The resulting viscous mass was diluted with water and extracted with ethyl acetate (2 x 50 mL). The combined organic layers were dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 30% ethyl acetate in hexane) affording 6-(4,4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyrazolo[l ,5-a]pyrimidine (1.0 g, 54%): lU NMR (400 MHz, Chloroform-d) delta 8.99 (s, 1H), 8.69 (s, 1H), 8.15 (d, / = 2.4 Hz, 1H), 6.67 (d, J = 2.4 Hz, 1H), 1.42 (s, 12H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,705263-10-1, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; HUESTIS, Malcolm; KELLAR, Terry; PATEL, Snahel; SHORE, Daniel; SIU, Michael; (260 pag.)WO2016/142310; (2016); 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. 330786-24-8, name is 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine. A new synthetic method of this compound is introduced below., Safety of 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Example 1-1 : Preparation of (i?)-3-(4-phenoxyphenyl)-l-(pyrrolidin-3-yl)-lH-pyrazolo[3,4- Patent; PHARMACYCLICS, INC.; CHEN, Wei; LOURY, David, J.; MODY, Tarak, D.; WANG, Longcheng; WO2013/10136; (2013); A2;,
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Reference of 769-42-6, 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.769-42-6, name is 1,3-Dimethylbarbituric acid, molecular formula is C6H8N2O3, molecular weight is 156.1393, as common compound, the synthetic route is as follows.

To a solution of 1,3-dimethylbarbituric acid (3.90 grams, 25.0 mmol) in 100 mL hot H2O was added a solution of benzaldehyde (2.65 grams, 25.0 mmol) in EtOH (20 mL). The resultant mixture was stirred vigorously while heating at reflux. After 5 hours, the mixture was allowed to cool to room temperature, and the precipitate was collected via filtration, washing with additional water. After drying overnight, this provided 5-benzylidene-l,3-dimethylpyrimidine-2,4,6-trione (5.90 grams, 97% yield) as a pale yellow solid.

Statistics shows that 769-42-6 is playing an increasingly important role. we look forward to future research findings about 1,3-Dimethylbarbituric acid.

Reference:
Patent; 3M INNOVATIVE PROPERTIES COMPANY; MOSER, William H.; TOWNSEND, Erik M.; THOMPSON, Zachary J.; CARUSO DAILEY, Mary M.; KROPP, Michael A.; (46 pag.)WO2019/152187; (2019); A1;,
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