Pyrimidines

Electric Literature of 302964-08-5, Adding some certain compound to certain chemical reactions, such as: 302964-08-5, name is 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide,molecular formula is C16H13Cl2N5OS, 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 302964-08-5.

In a 250 mL two-necked flask equipped with a reflux condenser,Compound I-6 (10.00 g, 25.4 mmol) was added at room temperature,Was dissolved in DMSO, 1-Boc-3-aminopyrrolidine (6.6 g, 35.6 mmol)DIPEA (N, N-diisopropylethylamine), 8.4 mL, 50.8 mmol) was slowly added under a nitrogen stream.Stir for 1 hAnd then heated to 80 C.TLC monitoring reaction. After completion of the reaction, the mixture was cooled to room temperature, water was added thereto, and the mixture was suctioned and washed with ice-cold water and beat with DCM to give a pure white intermediate. The intermediateTransfer to 10 mL of 30% TFA in methylene chloride and the reaction was stirred at room temperature, TLC was monitored, the reaction was completed, steamed to dryness, residualThe residue was washed three times with saturated sodium bicarbonate solution, filtered and the cake was dried to give 7.7% of I-8 in 68% yield.

According to the analysis of related databases, 302964-08-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Sciences Guangzhou Bio-pharmaceutical And Health Institute; Zhang Jiancun; Liu Lu; Chen Chaonan; Duan Anna; Tu Zhengchao; Yao Guoqiang; (42 pag.)CN106749223; (2017); A;,
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Adding a certain compound to certain chemical reactions, such as: 10457-14-4, 2,4-Bis((trimethylsilyl)oxy)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, 10457-14-4, blongs to pyrimidines compound. Product Details of 10457-14-4

Compound 3a (prepared according to Tetrahedron Letters, 1993, 8579; 16.4 g, 30 mmol) was dissolved in 75 mL of each DCE and ACN in a 400 mL high pressure vessel. To this was added Bis(TMS)uracil (12 g, 47 mmol) as solid and lastly Ag(OTf) (11 g, 43 mmol) was added. The reaction was sealed and heated at 135 C. for 90 minutes. The reaction mixture was then cooled to rt and precipitous AgBr filtered off. Solvents were then removed under vacuum and resulting residue was redissolved in EtOAc and aq. NaHCO3. Resulting mixture was extracted 3× with EtOAc, then organics were washed with water (1×), aq. sodium bicarbonate (2×), water (2×) and brine (1×) before drying over sodium sulfate. The solution was then filtered and evaporated to dryness. The residue was purified by silica gel chromatography with Hex:EtOAc to afford 3b (12.8 g; yield 74%). MS [M+H+]=581.9. 1H NMR: (400 MHz, CD3OD) delta 8.15 (1H, d, J=8.4 Hz), 5.68 (1H, d, J=8.4 Hz), 4.52 (1H, d), 4.26 (1H, m), 4.06 (1H, dd), 3.97 (1H, dd, J=12.8, 2.0 Hz), 3.73 (1H, dd, J=12.8, 2.0 Hz). MS [M-H+]=268.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10457-14-4, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; US2012/263678; (2012); 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. 2915-16-4, name is 2-Chloro-4,6-diphenylpyrimidine. A new synthetic method of this compound is introduced below., HPLC of Formula: C16H11ClN2

A mixture of 2-chloro-4,6-diphenylpyrimidine, 250mg (0.94 mmol), 4- (5-CHLORO-LH-INDOL-3-YL)-4-OXO-BUTYRIC acid 2- trimethylsilanyl-ethyl ester, 380mg (1.03 mmol), K2CO3 260mg (1.87 mmol), and N, N-dimethylaminopyridine, llmg (0.09 mmol) in 20mL DMSO was heated to 80 C for 6h. The mixture was cooled to room temperature and diluted with LOOML of EtOAc. The mixture was washed with sat. aq. LiCl (3XLOOML), water (3XLOOML), sat. aq. NACL (LXLOOML), and dried (MGS04). After the solution was concentrated, the residue was purified via column chromatography (eluted with 10% EtOAc-heptane) to afford the desired product in 0.47g (88%) as a pale yellow SOLID. 1H NMR (DMSO-d6) : 6 9.39 (s, 1H), 8.87 (d, 1H, J = 9.7Hz), 8.56 (s, 1H), 8.51-8. 48 (m, 3H), 8.26 (d, 1H, J = 2.7Hz), 7.64-7. 62 (m, 5H), 7.52 (dd, 1H, 9.7, 2.7Hz), 4.10 (dd, 2H, J = 9.0, 9. OHZ), 3.40 (t, 2H, J = 7.2Hz), 2.67 (t, 2H, J = 7.2Hz), 0.94 (dd, 2H, J = 9.0, 9. 0HZ), 0.00 (s, 9H).

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; THE INSTITUTES FOR PHARMACEUTICAL DISCOVERY, LLC; WO2004/99159; (2004); A1;,
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Reference of 1004-40-6 ,Some common heterocyclic compound, 1004-40-6, molecular formula is C4H5N3OS, 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 solution of 1-(bromomethyl)-4-tert-butylbenzene (2.00 ml, 9.00 mmol) in 10 mL of EtOH was added a solution of 6-amino-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (2.00 g, 12.0 mmol) in EtOH (35.0 ml, 9.00 mmol), water (4.00 ml, 9.00 mmol), and 3.45 M aqueous NaOH solution (4.00 ml, 13.0 mmol). The whole was heated at 50 C. After 16 h, LCMS showed mainly the product. The reaction was cooled down to rt and concentrated. Water was added until all solids had precipitated out of the solution. The solids were filtered off with an aid of water. White solid was obtained and was purified further by performing a column chromatography using 70:30 DCM:(90:10:1 DCM:MeOH:NH4OH). The product, 2-(4-tert-butylbenzylthio)-6-aminopyrimidin-4(3H)-one was obtained as a white solid (1.8 g, 69% yield). LCMS (ESI) Calcd for C15H19N3OS: [M]+ = 289. Found [M+H]+ = 290. The carbon shift data supported the structure of 6-amino-2-(4-tert-butylbenzylthio)pyrimidin-4(1H)-one. However, line-broadening in the 1D proton and carbon data suggested the double-bond is probably moving between the two nitrogens. Thus, 6-amino-2-(4-tert-butylbenzylthio)pyrimidin-4(1H)-one and 2-(4-tert-butylbenzylthio)-6-aminopyrimidin-4(3H)-one were in equilibrium in DMSO-d6. Proton and carbon chemical shift assignments for 2-(4-tert-butylbenzylthio)-6-aminopyrimidin-4(3H)-one in DMSO-d6 were shown below.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1004-40-6, its application will become more common.

Reference:
Article; Nguyen, Hanh Nho; Bregman, Howie; Buchanan, John L.; Du, Bingfan; Feric, Elma; Huang, Liyue; Li, Xingwen; Ligutti, Joseph; Liu, Dong; Malmberg, Annika B.; Matson, David J.; McDermott, Jeff S.; Patel, Vinod F.; Wilenkin, Ben; Zou, Anruo; McDonough, Stefan I.; Dimauro, Erin F.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 2; (2012); p. 1055 – 1060;,
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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 933702-55-7, name is 2-Chloropyrimidine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Safety of 2-Chloropyrimidine-5-carbaldehyde

To a suspension of bromo(2,6-difluoro-3,5-dimethoxybenzyl)triphenyl- 5-phosphane (Example 513, step (d) (4.9g, 9.29 mmol) in anhydrous THF (lOmL) was added 60% NaH (0.5g, 12.67 mmol) portionwise at 0 C under argon atmosphere. The resultant reaction mixture was stirred at room temperature for 12h. A solution of 2-chloropyrimidine-5-carbaldehyde (1.2g, 8.45 mmol) in anhydrous THF (5mL) was added dropwise for 15min. and stirring was continued for overnight at room temperature. The reaction mixture was quenched with ice water and ethyl acetate. The aqueous layer was separated and extracted with ethyl acetate (3x50mL). The combined organic phase was washed with brine, dried over Na2S04, filtered and concentrated under vacuum. The residue was purified by trituration with ether to afford desired title compound (0.45g, 17.3%) LCMS: m/z = 313.2 (M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 933702-55-7.

Reference:
Patent; EISAI R & D MANAGEMENT CO., LTD.; REYNOLDS, Dominic; HAO, Ming-Hong; WANG, John; PRAJAPATI, Sundeep; SATOH, Takashi; SELVARAJ, Anand; (128 pag.)WO2016/164703; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 32779-36-5, 5-Bromo-2-chloropyrimidine, 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, Formula: C4H2BrClN2, blongs to pyrimidines compound. Formula: C4H2BrClN2

INTERMEDIATE 6; Ethyl {5-[2-fpiperazin-l-yl)pyrimidin-5-yl]-2//-tetrazol-2-yl}acetate hydrochloride; Step 1 : tert-Butyl 4-(5 -bromopyrimidin-2-yl)piperazine- 1 -carboxylate; Into a 200 mL pressure flask equipped with a magnetic stir bar was added tert- butyl piperazine-1 -carboxylate (4.8 g, 25.8 mmol), 5-bromo-2-chloropyrimidine (5.0 g, 25.8 mmol) and 2-propanol (50 mL). DIPEA (5.0 mL, 28.4 mmol) was added, the vial was sealed and the reaction mixture heated to 120 °C for 1 h. The cooled reaction mixture was poured into a 250 mL separatory funnel containing water (125 mL) and extracted with EtOAc (3 x 75 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. Recrystallization from EtOAc (about 40 mL) and hexanes (about 150 mL) at -78 0C afforded crystals which were collected by filtration through filter paper on a Hirsch funnel under vacuum.

The synthetic route of 32779-36-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK FROSST CANADA LTD.; ISABEL, Elise; LACHANCE, Nicolas; LECLERC, Jean-Philippe; LEGER, Serge; OBALLA, Renata, M.; POWELL, David; RAMTOHUL, Yeeman, K.; ROY, Patrick; TRANMER, Geoffrey, K.; ASPIOTIS, Renee; LI, Lianhai; MARTINS, Evelyn; WO2010/94126; (2010); A1;,
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Application of 934524-10-4, 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.934524-10-4, name is 2,4-Dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C13H9Cl2N3O2S, molecular weight is 342.2, as common compound, the synthetic route is as follows.

Compound 10a (3.4 g, 10 mmol) was added to a 100 mL single-mouth bottle with magnetic stirring.And DMF (20 mL), stirred and dissolved, and added compound 11a (1.7 g, 10 mmol)And DIPEA (1.3g, 10mmol),The temperature was raised to 110 C under a nitrogen atmosphere and stirred to react overnight. Cool to room temperature,Add water (60 mL), extract with ethyl acetate (50 mL×3),Washed (100 mL×2), dried over anhydrous sodium sulfate, filtered and concentrated.The residue was passed through a silica gel column to give a white solid3.0 g, the yield was 63.2%.

Statistics shows that 934524-10-4 is playing an increasingly important role. we look forward to future research findings about 2,4-Dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; Shenzhen Tajirui Bio-pharmaceutical Co., Ltd.; Wang Yihan; Li Huanyin; (49 pag.)CN109851638; (2019); A;,
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Reference of 1421372-94-2, 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 1421372-94-2 as follows.

2 g of N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(1-methyl-1H-indol-3-yl)pyrimidin-2-amine was added to the reaction flask. 20mLDMA,After thorough stirring, 4.5 mL of dimethylamine and 1 g of DIEA were continuously added.After all the materials are stirred uniformly, the temperature is raised to 90 C, and the reaction is heated and refluxed for 2 to 3 hours.The spot plate is monitored until there is no raw material point, that is, the reaction is completed. Drop to room temperature, suction filtration,Washed, blast dried to constant weight, red solid, dry weight 2.40g

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1421372-94-2, its application will become more common.

Reference:
Patent; Jiangnan University; Hui Renjie; Feng Jing; Miao Lili; Zeng Shuai; (7 pag.)CN109438422; (2019); A;,
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Reference of 1193-24-4 , The common heterocyclic compound, 1193-24-4, name is 4,6-Dihydroxypyrimidine, molecular formula is C4H4N2O2, 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 31A 5-(4-Ethylphenyl)furo[2,3-d]pyrimidin-4(3H)-one A mixture of 7.50 g (35.44 mmol) of 1-[(Z)-2-chloro-2-nitroethenyl]-4-ethylbenzene and 4.97 g (44.30 mmol) of 4,6-dihydroxypyrimidine in 130 ml of isopropanol is heated at reflux. After 10 min, 13.22 ml (88.59 mmol) of 1,8-diazabicyclo[5.4.0]undecan-7-ene (DBU) are added dropwise, and the resulting reaction mixture is stirred under reflux for 4 h and then, after cooling, concentrated under reduced pressure. The residue is taken up in ethyl acetate and water. The phases are separated and the organic phase is washed with water and saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:2). This gives 2.8 g (32.9% of theory) of the title compound. HPLC (method 1): Rt=4.14 min. MS (DCI): m/z=241 (M+H)+. 1H-NMR (400 MHz, DMSO-d6): delta=12.68 (s, 1H), 8.19 (s, 1H), 8.17 (d, 1H), 7.88 (d, 2H), 7.28 (d, 2H), 2.63 (q, 2H), 1.22 (t, 3H).

The synthetic route of 1193-24-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2011/166163; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 148550-51-0, Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate, 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, Computed Properties of C8H10N2O4S, blongs to pyrimidines compound. Computed Properties of C8H10N2O4S

To a stirred solution of Example 2 (1.87 g, 6.94 mmol) in dry acetonitrile, potassium carbonate (2.87g, 20.8 mmol, spectrochem) and ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate were added and the resulting mixure was at rt for 12 h. It was filtered through celite and concentrated. Dichloromethane (25 mL) was added and the solution was washed with water, brine and dried over Na2SO4. After evaporation of the solvents, the crude product was purified by flash column chromatography to afford the title compound (white solid). 1H NMR (400 MHz, DMSO-d6): 8.74 (s, 2H), 6.85 (t, J = 7.8 Hz, 2H), 6.75 (d, J = 7.8 Hz, 1H), 5.98 (s, 2H), 4.25 (q, J = 6.8 Hz, 2H), 3.81 (s, 4H), 3.32 (s, 1H), 2.37-2.42 (m, 4H), 1.28 (d, J = 6.6 Hz, 6H). LCMS: (Method A) 385.2 (M+H), Rt. 3.22 min, 98.88percent (Max).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,148550-51-0, Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh S.; GIRI, Awadut Gajendra; KOEK, Johannes Nicolaas; (64 pag.)WO2017/144635; (2017); A1;,
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