Pyrimidines

932-52-5, A common compound: 932-52-5, name is 5-Aminopyrimidine-2,4(1H,3H)-dione,molecular formula is C4H5N3O2, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Equipped with a stirrer, thermometer, reflux condenser, the reaction vessel was added 1-amino-phthalide (2) 0.23mol, 5- aminouracil 0.28 mol, stannous chloride 0.31mol, 75% mass fraction cyclohexyl 230ml dioxane, stirred at 170 rpm and speed control, batches of 35% mass fraction of 0.13 mol sodium sulfite solution, the reaction was stirred 7H, filtered, and the filtrate was concentrated under reduced pressure the cyclohexane distilled off, added 630ml of 15% mass fraction of KCl , the precipitated solid was filtered, washed with sodium bromide solution, dried over anhydrous magnesium sulfate, was added to a mass fraction of 80% acetonitrile, and the solution temperature rises to 65 , 80min after filtration, the mass fraction of 95% nitromethane recrystallized to give crystals of 1- phthalide 5-amino-uracil 53.63g, yield 89%.

With the rapid development of chemical substances, we look forward to future research findings about 932-52-5.

Reference:
Patent; Chengdu Chester Technology Co., Ltd.; Peng, Fei; (5 pag.)CN105481837; (2016); A;,
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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. 1722-12-9, name is 2-Chloropyrimidine. A new synthetic method of this compound is introduced below., 1722-12-9

2-t-Butyl-4-(1-piperazinyl)-6-trifluoromethylpyrimidine (3) A solution of 60 g (0.25 mol) of the chloropyrimidine described above in 200 ml of ethanol was added dropwise to a boiling solution of 129 g (1.5 mol) of piperazine in 500 ml of ethanol over the course of 2 h, and then the mixture was boiled for a further 6 h. After the reaction was complete, the solvent was removed under reduced pressure, and the residue was mixed with 2 l of water. The product crystallized on cooling and was then filtered off with suction. Yield: 56 g (77% of theory) C13H19ClF3N4 (MW 288) m.p. 78-80 C. 1H-NMR (250 MHZ, CDCl3): d=1.3 (s, 9H); 1.8 (s, 1H); 3.0 (m, 4H); 4.7 (m, 4H); 6.6 (s, 1H) ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1722-12-9, 2-Chloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Hoger, Thomas; Starck, Dorothea; Treiber, Hans-Jorg; Schaefer, Bernd; Koser, Stefan; Thyes, Marco; Blank, Stefan; US2002/143179; (2002); 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. 698-29-3, name is 4-Amino-2-methylpyrimidine-5-carbonitrile. A new synthetic method of this compound is introduced below., 698-29-3

EXAMPLE 5 4-Amino-2-methyl-5-pyrimidinecarboxamidoxime A solution of hydroxylamine base, prepared from hydroxylamine hydrochloride (7.296 g., 0.105 mole) and potassium t-butoxide (11.783 g., 0.105 mole) in dimethyl sulfoxide (200 ml.) in a manner similar to that of Example 1, is allowed to react with 4-amino-2-methyl-5-pyrimidine carbonitrile (13.414 g., 0.100 mole). After addition of dimethyl sulfoxide (50 ml.), the mixture is heated at 40+-1 C. for 92 hours. The solid which separates is collected by filtration, successively washed with methanol (1*50 ml.) and water (3*50 ml.) then dried at 110/0.1 mm. The yield of colorless crystals melting at 263 C. dec. (uncorr.) is 10.059 g. (60.2%). A second crop is obtained by concentrating the combined filtrates in vacuo to give a white solid. This material is washed with water, dried at 110 C./0.1 mm. The yield of colorless crystals melting at 256 C. dec. (uncorr.) is 6.300 g. (37.6%). The total yield of crude product is 16.359 g. (97.8%). The combined fractions are recrystallized from 2-methoxyethanol (Darco G-60) affording 7.887 g. (47.2%) of colorless prisms melting at 264 C. dec. (uncorr.). Concentration of the mother liquors yields a second crop of colorless prisms melting at 265 C. dec. (uncorr.) in a yield of 6.258 g. (37.4%) total yield is 14.145 g. (84.6%). Analysis for: C6 H9 N5 O; Calculated: C, 43.11; H, 5.42; N, 41.90; Found: C, 43.04; H, 5.35; N, 42.12.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,698-29-3, 4-Amino-2-methylpyrimidine-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; American Home Products Corporation; US4323681; (1982); A;,
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Pyrimidine – Wikipedia

171887-03-9 , The common heterocyclic compound, 171887-03-9, name is N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide, molecular formula is C5H4Cl2N4O, 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.

To a suspension of N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide (10.0 g, 48.3 mmol) in 1,4-dioxane (400 mL) were added N,N-diisopropylethylamine (12.7 mL, 72.5 mmol) and piperazine-1 -carboxylic acid tert-butyl ester (9.8 g, 53.1 mmol). The mixture was stirred at 55C for 1 h. The solvent was removed in vacuo and the residue was partitioned between DCM and water. The aqueous phase was extracted with further DCM and the combined organic fractions were washed with brine, then dried (Na2SC>4) and evaporated in vacuo to give the title compound (17.1 g, 100%) as a white solid. LCMS (ES+) 357.4 (M+H)+, RT 1.08 minutes (method 3).

According to the analysis of related databases, 171887-03-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB PHARMA S.A.; KATHOLIEKE UNIVERSITEIT LEUVEN, K.U.LEUVEN R&D; BROOKINGS, Daniel Christopher; FORD, Daniel James; FRANKLIN, Richard Jeremy; GHAWALKAR, Anant Ramrao; KULISA, Claire Louise; NEUSS, Judi Charlotte; REUBERSON, James Thomas; WO2013/68458; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 56-09-7, 2-Amino-6-hydroxypyrimidin-4(3H)-one, 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, 56-09-7, blongs to pyrimidines compound. 56-09-7

General procedure: Typically, 2-aminopyrimidine-4,6-diol (1a, 0.5 mmol, 1.0 equiv)/2-methylpyrimidine-4,6-diol (1b, 0.5 mmol, 1.0 equiv), nitroolefins (2, 0.5 mmol, 1.0 equiv), as well as water (2.5 mL) were introduced into a 10 mL reaction vial. Then, the reaction vial was closed and stirred for given time at 90 C. Upon completion, the reaction mixture was cooled to room temperature and diluted with cold water (30 mL). The solid product was collected by filtration and was purified by recrystallization from hot 95% EtOH to afford the goal product 5-arylfuro[2,3-d]pyrimidin-4-ol (3) as off-white to yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,56-09-7, its application will become more common.

Reference:
Article; Li, Chunmei; Zhang, Furen; Tetrahedron Letters; vol. 58; 16; (2017); p. 1572 – 1575;,
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Adding some certain compound to certain chemical reactions, such as: 271-80-7, name is 1H-Pyrazolo[3,4-d]pyrimidine, 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 271-80-7. 271-80-7

Compound 8a1 (1 g, 8.33 mmol) was dispersed in 1,2-dichloroethane, and N-iodosuccinimide (2.3 g, 9.02 mmol) and TDA-1 (0.5 ml). The mixture was refluxed at 90 C. After 3 h, the solvent was evaporated and the residue was extracted with hot water. The solid residue was dissolved in ethyl acetate and purified with flash chromatography. The product was obtained as yellowish solid. (1.9 g, 92.7 %). Rf (dichloromethane/MeOH 20:1) 0.34. 1H NMR (400 MHz, DMSO-d6): delta 9.04 (s, 1 H, C6-H), 9.08 (s, 1 H, C2-H), 14.51 (s, 1 H, NH). 13C NMR (101 MHz, DMSO-d6): delta 93.80, 118.55, 153.30, 154.73, 156.52.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 271-80-7.

Reference:
Article; Zhu, Junfei; Li, Zhiwen; Wang, Qi; Liu, Yang; He, Junlin; Bioorganic and Medicinal Chemistry Letters; vol. 26; 18; (2016); p. 4462 – 4465;,
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1193-24-4, 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. 1193-24-4, name is 4,6-Dihydroxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

b. 4,6-Dichloro-pyrimidine-5-carbaldehyde A mixture of DMF (3.2 mL) and POCl3 (10 mL) at 0 C. was stirred for 1 h, treated with 4,6-dihydroxypyrimidine (2.5 g, 22.3 mmol), and stirred for 0.5 h at ambient temperature. The heterogeneous mixture was heated at reflux for 3 h and the volatiles were removed at reduced pressure. The residue was poured into ice water and extracted six times with ethyl ether. The organic phase was washed with aqueous NaHCO3, dried over Na2SO4 and concentrated to afford a yellow solid (3.7 g, 95%). 1H NMR (CDCl3) delta 10.46 (s, 1H), 8.90 (s, 1H).

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 1193-24-4, 4,6-Dihydroxypyrimidine.

Reference:
Patent; Gaul, Michael David; Xu, Guozhang; Baumann, Christian Andrew; US2006/281764; (2006); A1;,
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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 147118-37-4 as follows., 147118-37-4

Example 13 Preparation of 2-((4/?,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N- methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1 ,3-dioxan yl)acetate, methyl ester (O) from N-(4-(4-fluorophenyl)-5-formyl-6- isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide (J) and 2-((4 ?,6S)-6- ((benzo[d]thiazol-2-ylsulfonyl)methyl)-2,2-dimethyl-1 ,3-dioxan-4-yl)acetate methyl ester (N)(N) (J) (O) N-(4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide (0.35 g, I .O mmol) and 2-((4 ,6S)-6-((benzo[d]thiazol-2-ylsulfonyl)methyl)-2,2-dimethyl- 1 ,3-dioxan-4-yl)acetate methyl ester (0.45 g, 1.1 mmol) were added to 12 mL of dry THF After stirring for 10 min at 20C, the reaction mixture was cooled to -70C. At this temperature 1.5 mL of NaHMDS solution (1 M in THF, total 1.5 mmol) was added in 1 h keeping the temperature between -70 and -75C. When dosing was completed, the reaction mixture was stirred for 2h at -75C, then quenched with 10% aqueous NaHC03 (10 mL). The phases were separated. The aqueous layer was extracted with 2 x 25 mL of ethyl acetate. The combined organic phases were washed with 5% aqueous Na2C03 and concentrated under vacuum. The residue was crystallized from isopropanol to give 2-((4 ,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido) pyrimidin-5-yl)vinyl)-2,2-dimethyl-1 ,3-dioxan-4-yl)acetate, methyl ester as a solid (Compound O, 0.34 g, 0.63 mmol, 63% yield).

The chemical industry reduces the impact on the environment during synthesis 147118-37-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; DSM SINOCHEM PHARMACEUTICALS NETHERLANDS B.V.; DE LANGE, Ben; RIEBEL, Peter, Hans; WOLBERG, Michael; HEEMSKERK, Dennis; MINK, Daniel; WO2012/98048; (2012); 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 90213-66-4, name is 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. 90213-66-4

A solution of 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (1.00 g, 5.32 mmol) in THF (8 mL) was stirred at 0 C for 5 mm. Then sodium hydride (255 mg, 6.38 mmol) was added. The resulting mixture was stirred for 15 mm, then iodomethane (8.50 g, 53.20 mmol) was added. The reaction mixture was warmed to rt and stirred overnight. H20 (100 mL) was added to quench the reaction, and the resulting mixture was extracted with EtOAc (50 mL x 3). The combined organic phases were washed with brine (80 mL), dried over anhydrous Na2504, filtered, and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatograph (PE/EtOAc (v/v) = 10/1) to give the tilte compound as a white solid (1.00 g, 93 %).MS (ESI, pos. ion) m/z: 203.0 [M+H]t

Statistics shows that 90213-66-4 is playing an increasingly important role. we look forward to future research findings about 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; REN, Qingyun; TANG, Changhua; YIN, Junjun; YI, Kai; LEI, Yibo; WANG, Yejun; ZHANG, Yingjun; (215 pag.)WO2018/127096; (2018); A1;,
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Pyrimidine – Wikipedia

2380-63-4, 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. 2380-63-4, name is 1H-Pyrazolo[3,4-d]pyrimidin-4-amine, molecular formula is C5H5N5, 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.

Compound 1 (15 g, 111 mmol), NIS (30 g, 133.2 mmol) and DMF (150 ml) was stirred at 90 C for 4 h and then cooled to room temperature.Add 150 ml of water and filter with solids.Wash with 100 ml of water and 100 ml of ethanol in sequence.Dry at 70 C to obtain 23 g of solid,Yield: 79.4%.

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. 2380-63-4, 1H-Pyrazolo[3,4-d]pyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Pharmaceutical Industry Institute; China Pharmaceutical Industry Zongyuan; Zheng Nan; Hao Qun; Zhou Weicheng; Song Chengen; Zhang Peng; He Bo; Cao Yuanchao; Bi Siju; (56 pag.)CN109776544; (2019); A;,
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