Pyrimidines

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. 62459-02-3, name is 7-Benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine-2,4(1H,3H)-dione. A new synthetic method of this compound is introduced below., HPLC of Formula: C14H15N3O2

To a solution of 7-benzyl-6,8-dihydro-5H-pyrido[3,4-d]pyrimidine-2,4-diol (18.10 g, 70.35 mmol, 1.00 eq) in phosphoryl trichloride (165.00 g, 1.08 mol, 100 mL, 15.30 eq) was slowly added diisopropylethylamine (27.28 g, 211.05 mmol, 36.8 mL, 3.00 eq). The mixture was stirred at 110 C for 12 hours. The solvent was evaporated under reduced pressure and diluted with dichloromethane (150 mL), the suspension was slowly poured into ice-bath and adjusted to pH~7 with saturated sodium hydrogen carbonate solution (100 mL), the organic phase was separated and the aqueous was extracted with dichloromethane (150 mL x 3), the combined organic phase was dried over sodium sulfate, filtered and concentrated (phosphoryl trichloride was slowly poured into water under stirring and adjusted to pH~7 with saturated sodium hydrogen carbonate solution). The residue was purified by silica gel column chromatography (Petroleum ether/Ethyl acetate = 10/1 to 5/1). Compound 7 -benzyl-2, 4- dichloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine (6.70 g, 22.78 mmol, 32% yield) was obtained as a pale red solid pyrimidine-2, 4-diol (18.10 g, 70.35 mmol, 62% yield) was obtained as a white solid. LC/MS (ESI) m/z 294.0 [M+l] +; 1H-NMR (400MHz, CDCL) d 7.36 – 7.28 (m, 5H), 3.74 (s, 2H), 3.67 (s, 2H), 2.85 (s, 4H).

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, 62459-02-3, 7-Benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine-2,4(1H,3H)-dione.

Reference:
Patent; ARVINAS OPERATIONS, INC.; YALE UNIVERSITY; CREW, Andrew P.; HORNBERGER, Keith R.; WANG, Jing; DONG, Hanqing; BERLIN, Michael; CREWS, Craig M.; (1213 pag.)WO2019/195609; (2019); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 934524-10-4, 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 934524-10-4, name is 2,4-Dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of S2a (142mg, 0.415mmol) in nBuOH (4mL) was added DIPEA (67mg, 0.5187mmol) and 2-methoxyethylamine (37mg, 0.4980mmol). The mixture was stirred at 50C for 1 hr until starting material was consumed at which point the reaction was allowed to cool to rt and the nBuOH was removed under reduced pressure. The resulting residue was taken up in EtOAc and washed with saturated NH4Cl. The organic layer was isolated, dried over MgSO4, and concentrated under reduced pressure to yield 2-chloro-N-(2-methoxyethyl)-5-(p-tolylsulfonyl)pyrrolo[3,2-d]pyrimidin-4-amine (S3a) as a solid (100mg, 63% yield).

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 934524-10-4, 2,4-Dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Article; Wormald, Michael M.; Ernst, Glen; Wei, Huijun; Barrow, James C.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 19; (2019);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 591-55-9, Adding some certain compound to certain chemical reactions, such as: 591-55-9, name is 5-Aminopyrimidine,molecular formula is C4H5N3, 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 591-55-9.

To a solution of 2-isocyano-2-methylpropane (2.033 mL, 17.98 mmol), S-phenyl benzenesulfonothioate (1800 mg, 7.19 mmol) and pyrimidin-5-amine (1026 mg, 10.79 mmol) in 2-methyltetrahydrofuran (2-MeTHF) (10 mL), copper(I) iodide (137 mg, 0.719 mmol) was added. The reaction mixture was stirred at 75C for 16 hrs. The reaction mixture was filtered through silica and the solvent was evaporated and the product purified by silica gel chromatography with hexane and ethyl acetate to obtain the title compound phenyl N-(tert- butyl)-N’-(pyrimidin-5-yl)carbamimidothioate (1.98 g, 6.91 mmol, 96 % yield). LC-MS m/z 287.2(M+H)+, 1.06 min (ret. Time).

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. 591-55-9, 5-Aminopyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CALLAHAN, James Francis; COLANDREA, Vincent J.; COOPER, Anthony William James; GOODWIN, Nicole Cathleen; HUFF, Chelsea Ariane; KARPIAK, Joel; KERNS, Jeffrey K.; NIE, Hong; (404 pag.)WO2018/109647; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 62458-96-2 , The common heterocyclic compound, 62458-96-2, name is 7-Benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4(3H)-one, molecular formula is C14H15N3O, 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 1362-[3-(7-Benzyl-4-oxo-5,6,7,8-tetrahydro-4H-pyrido[3,4-d]pyrimidin-3-yl)-phi dimethyl- 1, 2,3 ,4-tetrahydro-quinoline-6-carboxylic acidA mixture of 2-(3-bromo-phenyl)-3,3-dimethyl-l,2,3,4-tetrahydro-quinoline-6-carboxylic acid (360 mg, 1.0 mmol), 7-benzyl-5,6,7,8-tetrahydro-3H-pyrido[3,4-d]pyrimidin-4-one (300 mg, 1.3 mmol), copper(I) iodide (80 mg, 0.4 mmol), N, N-dimethylglycine hydrochloride (117 mg, 0.8 mmol) and potassium carbonate (769 mg, 5.6 mmol) in dimethyl sulfoxide (5 mL) was stirred at 120C for 16 h. Then the reaction mixture cooled to room temperature. The reaction mixture was extracted with ethyl acetate (2 x 150 mL), washed with water (2 x 50 mL) and saturated aqueous ammonium chloride solution (2 x 50 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by Waters automated flash system (column: Xterra 30 mm x 100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded 2-[3-(7-benzyl-4-oxo-5,6,7,8-tetrahydro-4H- pyrido[3,4-d]pyrimidin-3-yl)-phenyl]-3,3-dimethyl-l,2,3,4-tetrahydro-quinoline-6- carboxylic acid (320 mg, 61%) as a white solid : LC/MS m/e calcd for C32H32N4O3 (M+H)+: 521.64, observed: 521.2.

The synthetic route of 62458-96-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; CHEN, Li; FENG, Lichun; HUANG, Mengwei; LIU, Yongfu; WU, Guolong; WU, Jim, Zhen; ZHOU, Mingwei; WO2011/128251; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 4994-86-9, 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 4994-86-9 as follows.

General procedure: 3-(3-(4-(aminomethyl)benzyl)isoxazol-5-yl)pyridin-2-amine diformate (Intermediate D, 80mg, 0.22mmol) was dissolved in DMSO (0.5mL). N-ethyl-N-isopropylpropan-2 -amine (83mg, 0.65mmol) and 2,6-difluoropyridine (l48mg, l .29mmol) were added and the mixture was stirred for 2h at l20C. The mixture was diluted with water (l5mL) and extracted with ethyl acetate (3 x 10 mL). The combined organic layers were washed with brine (10 mL), dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Si02, hexane/ethyl acetate) to yield N-(4-((5-(2-aminopyridin-3-yl)isoxazol-3-yl)methyl)benzyl)-6-fluoropyridin-2 -amine (47mg, 0T3mmol, 58%) as a white solid. 500 MHz NMR (DMSO-d6) d 8.08 (dd, .7= 4.8, 1.8 Hz, 1H), 7.86 (dd, J= 7.7, 1.8 Hz, 1H), 7.52 – 7.40 (m, 2H), 7.28 (s, 4H), 6.79 (s, 1H), 6.69 (dd, J= 7.7, 4.8 Hz, 1H), 6.35 (dd, J= 8.0, 2.5 Hz, 1H), 6.25 (s, 2H), 6.08 (dd, J= 7.6, 2.2 Hz, 1H), 4.38 (d, J= 6.0 Hz, 2H), 4.00 (s, 2H). MS: 376.3 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4994-86-9, its application will become more common.

Reference:
Patent; AMPLYX PHARMACEUTICALS, INC.; TRZOSS, Michael; COVEL, Jonathan; SHAW, Karen Joy; WEBB, Peter; (240 pag.)WO2019/113542; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 16462-27-4, 2,4-Diaminopyrimidine-5-carbonitrile, 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, SDS of cas: 16462-27-4, blongs to pyrimidines compound. SDS of cas: 16462-27-4

A solution of 0.41 g (2 mmol) of the compound of formula V was dissolved in methanol and 0.13 g (2 mmol) of Raney nickel (catalyst) was reacted with H2 at room temperature for 24 h, and an appropriate amount of water was added, extracted with ethyl acetate, The residue was purified by silica gel column chromatography (eluent: methanol: dichloromethane = 1: 30, v / v), and the residue was purified by silica gel column chromatography. To give a white solid (compound of formula V) in 81% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16462-27-4, 2,4-Diaminopyrimidine-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; East China University of Science and Technology; Zhu Jin; Huang Jin; Chen Wenhua; Yao Xue; Ling Dazheng; Wang Manjiong; Jiang Hualiang; Li Jian; (21 pag.)CN106938997; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 10320-42-0, name is 2-Chloro-5-nitropyrimidine. A new synthetic method of this compound is introduced below., name: 2-Chloro-5-nitropyrimidine

To a solution of 2-chloro-5-nitropyrimidine (0.200 g, 1.254 mmol) and 6-oxa-3-azabicyclo[3.1.1]heptane 4-methylbenzenesulfonate (0.394 g, 1.452 mmol) in 2Me-THF (6 mL), was added triethylamine (0.4 ml, 2.870 mmol). The reaction was stirred at rt overnight. The reaction was partitioned with DCM and water. The organic extract washed with brine and dried over sodium sulfate to give I-35C. ES/MS: 223.0.9 (M+H+). 1H NMR (400 MHz, Chloroform-d) delta 9.18 (s, 1H), 4.80 (d, J=6.6 Hz, 2H), 4.08 (d, J=13.8 Hz, 2H), 3.97 (d, J=13.9 Hz, 2H), 3.37 (q, J=7.4 Hz, 1H), 1.95 (d, J=9.2 Hz, 1H).

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, 10320-42-0, 2-Chloro-5-nitropyrimidine.

Reference:
Patent; Gilead Sciences, Inc.; Bacon, Elizabeth M.; Brizgys, Gediminas; Chin, Elbert; Chou, Cheinhung; Cottell, Jeromy J.; Link, John O.; Taylor, James G.; Tse, winston C.; Wright, Nathan E.; Yang, Zheng-Yu; Zhang, Jennifer R.; Zipfel, Sheila M.; US2018/230157; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1224944-77-7, 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 1224944-77-7 as follows.

A mixture of ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate (1.00 g, 4.43 mmol), 2-(2,5-difluorophenyl)pyrrolidine (Intermediate 2, 853 mg, 4.65 mmol) and KF (1.28 g, 22.1 mmol) in DMSO (14 mL) was stirred at 180 C. for 2 hours. After being cooled to room temperature, the reaction mixture was poured into water. The mixture was stirred for 30 min. A precipitated solid was collected by filtration and dried under vacuum to afford ethyl 5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (1.51 g, 91%) as a yellow solid. 1H-NMR (CDCl3, Varian, 400 MHz): delta 1.30-1.49 (3H, m), 1.98-2.18 (3H, m), 2.43-2.58 (1H, m), 3.95-4.20 (2H, m), 4.25-4.48 (2H, m), 5.18-5.23 (1H, m), 5.82-5.94 (1H, m), 6.68-6.80 (1H, m), 6.86-6.98 (1H, m), 7.00-7.12 (1H, m), 8.08-8.22 (1H, m), 8.29 (1H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1224944-77-7, its application will become more common.

Reference:
Patent; HANDOK INC.; CMG Pharmaceutical Co., Ltd.; Kim, Moonsoo; Lee, Chaewoon; Lee, Gilnam; Yoon, Cheolhwan; Seo, Jeongbeob; Kim, Jay Hak; Lee, Minwoo; Jeong, Hankyul; Choi, Hyang; Jung, Myung Eun; Lee, Ki Nam; Kim, Hyun Jung; Kim, Hye Kyoung; Lee, Jae Il; Lee, MinWoo; Kim, Misoon; Choi, Soongyu; (124 pag.)US2016/168156; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1683-75-6, 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. 1683-75-6, name is 2-Amino-4-chloro-5-fluoropyrimidine, molecular formula is C4H3ClFN3, 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.

The reaction bottle was added with mechanical stirring, and then SM4 (200.0g, 0.666mol) and SM6 (98.0g, 0.666mol) were added in sequence.Palladium acetate (7.4g, 0.033mol), tripotassium phosphate trihydrate (354.0g, 1.332mol), 1,4-dioxane (1.4L) and water (0.6L).Under nitrogen protection, the reaction liquid was heated to 100C, kept under heat and stirred for 4 hours, and the final control of the sampling was completed.The reaction solution was cooled to room temperature, the layers were separated, the organic phase was concentrated, and concentrated hydrochloric acid (250 mL) was added to the concentrated residue.Water (750 mL) and activated carbon (10.0 g) were stirred at room temperature for 1 hour.Filtration, the filtrate was reduced to 0 ~ 5 , then 20% aqueous sodium hydroxide solution (1.0 L) was added dropwise, stirred, filtered,After drying, 163.0 g of light yellow solid was obtained with a yield of 85.8% and a purity of 96.8%.

According to the analysis of related databases, 1683-75-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jiangsu Haosen Pharmaceutical Group Co., Ltd.; Shanghai Hansen Bio-pharmaceutical Technology Co., Ltd.; Liu Fuping; Zhang Jingtao; Wu Liyuan; (48 pag.)CN111138413; (2020); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 1215787-31-7, name is 6-Bromo-4-chloropyrido[2,3-d]pyrimidine, the common compound, a new synthetic route is introduced below. SDS of cas: 1215787-31-7

General procedure: To a solution of compound 4 (2.43 g, 0.01 mol) in 25 mL dioxane was added 1-(2,6-Dichloro-3-fluorophenyl)ethan-1-amine (3.12 g, 0.015 mol), and then the reaction mixture was stirred at room temperature overnight. After that, the mixture was poured into 150 mL H2O, and then the resulting precipitate was filtered, washed with 50% ethanol, and dried overnight under vacuum to give 5a as white solid (3.58 g, yield, 86%).

The synthetic route of 1215787-31-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hou, Ju; Wan, Shanhe; Wang, Guangfa; Zhang, Tingting; Li, Zhonghuang; Tian, Yuanxin; Yu, Yonghuan; Wu, Xiaoyun; Zhang, Jiajie; European Journal of Medicinal Chemistry; vol. 118; (2016); p. 276 – 289;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia