Pyrimidines

Adding a certain compound to certain chemical reactions, such as: 60025-09-4, 4-Amino-6-chloropyrimidine-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, Quality Control of 4-Amino-6-chloropyrimidine-5-carbonitrile, blongs to pyrimidines compound. Quality Control of 4-Amino-6-chloropyrimidine-5-carbonitrile

General procedure: To a solution of 7a (80mg, 0.18mmol, 1 equiv), 4-amino-6-chloropyrimidine-5-carbonitrile (31mg, 0.2mmol, 1.1 equiv) in BuOH was added DIPEA (0.06mL, 0.36mmol, 2 equiv). The mixture was reacted under microwave at 130C for 20min. After completion, the solvent was removed under reduced pressure. The residue was redissolved in CH2Cl2. The crude was further purified via silica gel chromatography to give compound 8a as white solid (81mg, 80%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60025-09-4, 4-Amino-6-chloropyrimidine-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Article; Wei, Manman; Zhang, Xi; Wang, Xiang; Song, Zilan; Ding, Jian; Meng, Ling-Hua; Zhang, Ao; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 1156 – 1171;,
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Pyrimidine – Wikipedia

Reference of 20781-06-0, Adding some certain compound to certain chemical reactions, such as: 20781-06-0, name is 2,4-Diaminopyrimidine-5-carboxaldehyde,molecular formula is C5H6N4O, 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 20781-06-0.

A. Preparation of 2,6-dipivaloylamino-5-carboxaldehydepyrimidine STR40 To a 250 mL round bottom flask flame dried under a nitrogen atmosphere was suspended 2.0 g (14.5 mmol) of 2,6-diamino-5-carboxaldehydepyrimidine [as described in J. Med. Chem., 26:667-673 (1983)] in 16 mL of anhydrous DMF, followed by the addition of 16 mL (78.9 mmol) of trimethylacetic anhydride. This mixture was then heated to 160 C. for 1 hours. The dark brown solution was cooled to ambient temperature and the volatiles were removed in vacuo. The crude residue was dissolved in 100 mL of MeCl2 and washed 3 times with 100 mL hot water, dried over Na2 SO4, and removed in vacuo. The solid was then flash chromatographed on silica gel eluding with 1:1 EtOAc/MeCl2. The correct fractions were combined and removed in vacuo to give 2.4 g (54%) of 2,6-dipivaloylamino-5-carboxaldehydepyrimidine as a white solid. Rf =0.21 (1:1 EtOAc/MeCl2) mp.=182-184 C. Mass (FAB) M+1 HRMS=Calcd.: 307.1770; Found: 307.1758 IR (KBr, cm-1)=802, 836, 1001, 1130, 1208, 1256, 1327, 1370, 1397, 1452, 1485, 1625, 1663, 1718, 2969, 3223, 3511 UV (EtOH) lambdamax =291, 248 (epsilon=14,856, 28,220) 1 H NMR (300 MHz, CDCl3) delta1.35 (S, 9H), 1.38 (S, 9H), 8.61 (br s, 1H), 8.87 (s, 1H), 9.85 (s, 1H), 11.42 (br 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. 20781-06-0, 2,4-Diaminopyrimidine-5-carboxaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eli Lilly and Company; US5426110; (1995); A;,
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Pyrimidine – Wikipedia

Synthetic Route of 51-20-7, 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.51-20-7, name is 5-Bromouracil, molecular formula is C4H3BrN2O2, molecular weight is 190.9828, as common compound, the synthetic route is as follows.

To a mixture of 5-bromo-1H-pyrimidine-2,4-dione (400.6 mg, 2.1 mmol, 1.0 eq) and 1-([1,1?-biphenyl]-3-yl)piperazine (500 mg, 2.1 mmol, 1.0 eq) in DMSO (10.00 mL) was addedpotassium fluoride (182.8 mg, 3.15 mmol, 1.5 eq). The resulting mixture was stirred at 110 C for 8 hours, cooled to room temperature, poured into water and the gray precipitate collected by suction filtration. The gray solid was washed with 100 mL of 1:1 EtOAc: petroleum ether to give 5-(4-([ 1,1 ?-biphenyl]-3 -yl)piperazin- 1 -yl)pyrimidine-2,4(1H,3H)-dione (500.0 mg, 1.4mmol, 68.3% yield) as a gray solid. LCMS Method B (ESI+): Expected m/z 349.1 (M+1) found m/z 349.1 (M+1), RT: 2.16 Mm.

Statistics shows that 51-20-7 is playing an increasingly important role. we look forward to future research findings about 5-Bromouracil.

Reference:
Patent; VYERA PHARMACEUTICALS, LLC; WELSCH, Matthew; HOPPER, Allen, T.; THOMAS, Stephen, B.; (136 pag.)WO2019/32458; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 4595-61-3, Pyrimidine-5-carboxylic acid, 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, Safety of Pyrimidine-5-carboxylic acid, blongs to pyrimidines compound. Safety of Pyrimidine-5-carboxylic acid

Compound 25 BTC (1 .15 eq, 0.100 mmol, 30 mg) was dissolved in dry THF (5 ml) under an atmosphere of argon. Pyrimidine-5-carboxylic acid (3.5 eq, 0.305 mmol, 67 mg) was added. syn-Collidine (8 eq, 0.700 mmol, 0.092 ml) was slowly added via syringe and the white suspension was stirred at room temperature for 10 min. The amine (1 eq, 0.087 mmol, 70 mg) and DIPEA (10 eq, 0.872 mmol, 0.150 ml) were added via syringe. The reaction mixture was stirred for 12 h at room temperature and quenched by the addition of water. After removing the organic solvent under reduced pressure the aqueous phase was extracted with EtOAc (3 x 50 ml). The organic phase was washed with saturated NaHC03 solution (2 x 50 ml), aqueous HCI solution (5 percent, 2 x 50 ml), water (1 x 50 ml) and brine (1 x 50 ml). After drying over Na2S04 and filtration, the solvent was removed under reduced pressure. Column chromatography (CHCI3:MeOH; 1 .5 percent MeOH) yielded the product as an yellow solid (55 mg, 65 percent). The solid (1 eq, 0.058 mmol, 53 mg) and phenylsilane (8 eq, 0.467 mmol, 0.057 ml) were dissolved in dry THF under an atmosphere of argon and exclusion of light. Pd[P(Ph)3]4 (0.5 eq, 0.029 mmol, 34 mg) was added and the mixture was stirred 12 h at room temperature. After adding 3 drops of acetic acid the solvent was removed under reduced pressure. The product was isolated after preparative HPLC purification as a white powder (9 mg, 20 percent). H-NMR (DMSO-ds, 400 MHz): delta [ppm] 3.08 (m, 1 H), 3.17 (dd, Ji = 17.1 Hz, J2 = 5.2 Hz, 1 H), 3.77 (s, 3H), 3.92 (s, 3H), 4.99 (m, 1 H), 7.56 (d, J = 8.9 Hz, 1 H), 7.81 (m, 3H), 7.91 (d, J = 8.9 Hz, 2H), 7.99 (d, J= 8.4 Hz, 5H) 8.32 (d, J = 9.4 Hz, 1 H), 9.1 1 (d, J = 7.5 Hz, 1 H), 9.32 (s, 2H), 9.39 (s, 1 H), 9.70 (s, 1 H), 10.61 (s, 1 H), 10.87 (s, 1 H), 1 1 .15 (s, 1 H), 1 1 .57 (s, 1 H). HR-MS: [M-H]- calculated: 787.21068 [M-H]- found: 787.21283

The synthetic route of 4595-61-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TECHNISCHE UNIVERSITAeT BERLIN; CENTRE DE COOPERATION INTERNATIONALE EN RECHERCHE AGRONOMIQUE POUR LE DEVELOPPEMENT (CIRAD); SUeSSMUTH, Roderich; KRETZ, Julian; SCHUBERT, Vivien; PESIC, Alexander; HUeGELLAND, Manuela; ROYER, Monique; COCIANCICH, Stephane; ROTT, Phillipe; KERWAT, Dennis; GRAeTZ, Stefan; WO2014/125075; (2014); A1;,
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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.10320-42-0, name is 2-Chloro-5-nitropyrimidine, molecular formula is C4H2ClN3O2, molecular weight is 159.5306, as common compound, the synthetic route is as follows.Recommanded Product: 10320-42-0

The first step: vacuuming a dry 50 mL reaction jar with nitrogen Three times, then add 2-fluoroaniline to the reaction jar(111 mg, 1.0 mmol, 1.0 equiv), add 10.0 mL of dried acetonitrile and stir until2-fluoroaniline is completely soluble,Then 2-chloro-5-nitropyrimidine (0.1593 g, 1.0 mmol, 1.0 equiv) was added to the reaction flask. Whole mixture in nitrogenThe reaction was carried out under a gas pressure for 4-5 hours. The reaction is detected by TLC, and if the reaction of aniline is detected, it can be stopped.Stop the reaction. The experimental treatment is to drain the solution in the reaction; dissolve the solute in the reaction flask with ethyl acetate, and transfer toIn a 100 mL round bottom flask, add 2 mL (200-300 mesh) of silica gel to the round bottom flask for spin-drying (petroleum ether and acetic acid B).Ester) over silica gel in the column. Wait until the intermediate product is pale yellow crystal N-(2-fluorophenyl)-5-nitropyrimidin-2-amine (209 mg, 97% yield)rate).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10320-42-0, 2-Chloro-5-nitropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Jinan University; Feng Pengju; Chen Tianfeng; Chen Junfeng; Huang Yifeng; (25 pag.)CN108148005; (2018); A;,
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Pyrimidine – Wikipedia

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 22536-66-9, name is 2-Chloropyrimidine-4-carboxamide. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

1.4. 2-[1-[2-(2-Methoxyphenoxy)ethyl]piperidin-4-yl-amino]pyrimidine-4-carboxamide, hydrochloride. 2.1 g (0.0073 mol) of 1-[2-(2-methoxyphenoxy)-ethyl]piperidin-4-amine, 1.15 g (0.0073 mol) of 2-chloropyrimidine-4-carboxamide and 3 g (0.0219 mol) of potassium carbonate in solution in 42 ml of N,N-dimethylformamide are introduced into a 100 ml round bottom flask. The mixture is stirred for 48 hours at room temperature, it is poured into water and then extracted three times with ethyl acetate. The organic phase is washed once with water, dried over sodium sulphate, filtered and the filtrate is concentrated under reduced pressure. The base is recrystallized from 2-propanol to give 0.7 g of base. 19 ml of a 0.1N hydrochloric acid solution in 2-propanol are added to the base in solution in a mixture of dichloromethane and 2-propanol. The solvent is evaporated under reduced pressure and the hydrochloride is recrystallized from 2-propanol. 0.26 g of compound are obtained. Melting point: 194-196 C.

With the rapid development of chemical substances, we look forward to future research findings about 22536-66-9.

Reference:
Patent; Synthelabo; US5246939; (1993); A;,
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Pyrimidine – Wikipedia

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. 945016-63-7, name is 3-(2-Chloropyrimidin-4-yl)-1H-indole. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 945016-63-7

Sodium hydride (2.7 g, 60% in mineral oil) was added portionwise to 3-(2- chloropyrimidin-4-yl)-1H-indole (12 g) in THF (250 mL) at 0 C. The resulting mixture was stirred at 0 C for 30 mm before CR93 (1.3 equiv.) was added. The mixture was stirred at 0 C for 1 h. The reaction was quenched by the addition of saturated aqueous NaHCO3 solution (400 mL) and EtOAc (400 mL). The orgamic layer was washed with saturated brine (200 mL). The organic layer was evaporated to afford crude product (compound 4, 9.3 g) as a pale orange solid.

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, 945016-63-7, 3-(2-Chloropyrimidin-4-yl)-1H-indole.

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

Adding a certain compound to certain chemical reactions, such as: 1119280-68-0, 2-Chlorothieno[3,2-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, Recommanded Product: 2-Chlorothieno[3,2-d]pyrimidine, blongs to pyrimidines compound. Recommanded Product: 2-Chlorothieno[3,2-d]pyrimidine

2-chlorothieno[3,2-d]pyrimidine (4, 0.9 g, 5 mmol) was taken up in acetonitrile (10 mL) to form a mixture. Bromine (0.450 mL, 8 mmol), followed by HI04 (0.558 g, 2 mmol) were added to the mxiture and the mixture was refluxed for 2 h. Thin layer chromatography (TLC) of the reaction mixture showed complete conversion of compound 4 to compound 5. The reaction mixture was then cooled and poured in ethyl acetate to form a mixture. Water, followed by saturated sodium thiosulfate were added to the mixture to form a biphasic mixture having an organic layer and an aqueous layer. The organic layer was separated from the aqueous layer, washed sucessively with bicarbonate and brine, dried over Na2S04 and concentrated to obtain 7-bromo-2-chlorothieno[3,2-d]pyrimidine (5, l g, 68.96%). ‘HNMR (CDCl3): 9.18 (s, 1 H), 8.10 (s, 1 H).

The synthetic route of 1119280-68-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GATEKEEPER PHARMACEUTICAL, INC.; GRAY, Nathanael, S.; ZHOU, Wenjun; WO2011/79231; (2011); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 113583-35-0, 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. 113583-35-0, name is 2-Methanesulfonyl-4,6-dimethoxypyrimidine. A new synthetic method of this compound is introduced below.

4-Hydroxypyridine 1.88g (0.02 mol) and 4,6-dimethoxypyrimidine-2-yl methyl sulfone 4.36g (0.02 mol) were dissolved in DMF 100 ml, and K2CO3 3.3g (1.2 eq) was added thereto. Then, the temperature was maintained at 95C while the mixture was stirred over night. The reacted solution was added to water 100 ml, extracted with diethyl ether, dried with MgSO4, and distilled under reduced pressure to obtain residue. Through purification with silica gel column chromatography, a solid material 3.73g (80%) was obtained: 1H NMR (CDCl3); 3.73 (s, 6H), 5.49 (s, 1H), 6.85-8.42 (m, 4H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,113583-35-0, 2-Methanesulfonyl-4,6-dimethoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; SNU R&DB Foundation; Korea Research Institute Of Chemical Technology; EP2497768; (2012); A2;,
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. 862730-04-9, name is 3-Iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine. A new synthetic method of this compound is introduced below., HPLC of Formula: C8H10IN5

Synthesis of 3-(1H-indol-4-yl)-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (BA91); A solution of 1H-indol-4-yl-4-boronic acid (40 mg, 0.25 mmol) in EtOH (1.65 ml) was added to a solution of 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (30 mg, 0.1 mmol) in DME (6 ml). Pd(PPh3)4 (30 mg, 0.03 mmol) and saturated Na2CO3 (0.95 ml) were added and the reaction was heated to 80 C. under an argon atmosphere overnight. After cooling, the reaction was extracted with saturated NaCl and CH2Cl2. Organic phases were combined, concentrated in vacuo and purified by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA91 (14.6 mg, 50% yield). ESI-MS (M+H)+ m/z calcd 293.1, found 293.1.

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, 862730-04-9, 3-Iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine.

Reference:
Patent; Regents of the University of California; US2007/293516; (2007); A1;,
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Pyrimidine – Wikipedia