Pyrimidines

Synthetic Route of 607740-08-9 , The common heterocyclic compound, 607740-08-9, name is 4-(3,5-Dibromophenyl)-2,6-diphenylpyrimidine, molecular formula is C22H14Br2N2, 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.

Under a nitrogen stream3,6-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9-phenylcarbazole 10.0 gmmol),4- (3,5-Dibromo-phenyl) -2,6-diphenyl-pyrimidine 9.41 g (20.19 mmol) K2CO3 16.7 g,800 ml of toluene,Then, 200 ml of a mixed solution was put into a 2-liter 2-neck round bottom flask, stirred for 30 minutes at room temperature,Pd (PPh3) 4 (70 mg, 0.61 mmol) was added thereto and refluxed for 18 hours.After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO 4 and filtered.After removal of the solvent of the obtained organic layer, the residue was purified by column chromatography to obtain the target compound Macrocycle-II (4.93 g, yield 22.3%).

The synthetic route of 607740-08-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Doosan Co., Ltd; Um Min-sik; Kim Tae-hyeong; Baek Yeong-mi; (20 pag.)KR101847236; (2018); B1;,
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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. 4270-27-3, name is 6-Chloropyrimidine-2,4(1H,3H)-dione, the common compound, a new synthetic route is introduced below. Recommanded Product: 4270-27-3

Into a dry Schlenk reaction tube was added 6-chloropyrimidine-2,4 (1H, 3H) -dione (0.29 g, 2.0 mmol), pyridin-2-ylboronic acid (0.3 g, 2.2 mmol), Tetrakis (triphenylphosphine) palladium (29 mL, 0.025 mmol) and K2CO3 (0.33 g, 2.4 mmol) were added , then 1,4-dioxane (10 mL), water (2 mL) was added under nitrogen atmosphere for 4 h at 45 C. After completion of the reaction, the solvent was removed under reduced pressure, and the residue was dissolved in ethyl acetate , then separated by silica gel column chromatography and eluting with petroleum ether / ethyl acetate 20: 1 to give a pale yellow solid 6- (pyridin-2-yl)pyrimidine-2,4 (1H,3H)-dione. Its 0.28 g of a pale yellow solid, 98% purity, yield 74%.

The synthetic route of 4270-27-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mudanjiang Medical School; Song Jing; Sun Zhiguo; Han Guangyu; Li Hailin; Wang Wei; (15 pag.)CN106946851; (2017); A;,
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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 131860-97-4, name is (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate

Toluene (40.8g) was stirred and heated to 700C. Methyl (E)-2-{2-[6-chloropyrimidin-4- yloxy]phenyl}-3-methoxyacrylate (24.2g at 98%w/w, 0.074mols), DABCO (0.85g at 98%w/w, 0.007mols) and 2-cyanophenol (9.9g at 97.5%w/w, O.Odeltamols) were added at 10 minute intervals, maintaining the temperature at 7O0C. After a further 10 minutes DBU , (13.8g at 98%w/w, 0.09mols) was added over 5.5 minutes. During the addition the temperature went up to 78C and cooling was applied to maintain 7O0C. The reaction mixture was stirred at 700C for 90 minutes (still 35.8 area% methyl (E)-2-{2-[6- chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate unreacted by GC analysis). The reaction temperature was raised to 800C and stirring continued for another 90 minutes at which time the reaction was still not complete (14.2 area% methyl (E)-2- {2-[6-chloropyrimidin-4- yloxy]phenyl}-3-methoxyacrylate unreacted by GC analysis). The temperature was raised to 1000C and stirring continued for a further 60 minutes to complete the reaction. The reaction mixture was cooled to 700C before hot water (75C) (78.3g) was added. The mixture was stirred for 15 minutes at 70-75C, then settled and the aqueous phase separated. A second water wash (78.3g) was applied in the same way. The toluene phase (66.6g) contained methyl (J£)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (32.8%w/w), 73.3% of theory.

With the rapid development of chemical substances, we look forward to future research findings about 131860-97-4.

Reference:
Patent; SYNGENTA LIMITED; WO2008/43978; (2008); A1;,
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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. 13544-44-0, name is 2,4-Dichloro-5-iodopyrimidine, the common compound, a new synthetic route is introduced below. SDS of cas: 13544-44-0

The mixture of 2,4-dichloro-5-iodopyrimidine (400 mg) and N-(3-aminopropyl)carbamic acid tert-butyl ester (0.24 ml) in 3 ml of ACN with 0.23 ml od TEA was stirred overnight at rt. The product was then precipitated by the addition of water and collected and dried as an opaque yellow oil. 20 mg of this product was then reacted with N-(3-aminophenyl)pyrrolidine-1-carboxamide (14.9 mg, prepared previously28) overnight at 115C in 1 ml of MeOH in a sealed vial with 1.5 mul concn HCl. Then 1 ml of TFA was added overnight at rt to deprotect. The product was then purified by RP HPLC to give the final product, which was then lyophilized to give a white powder. Overall yield of 16%.

The synthetic route of 13544-44-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lazarus, Michael B.; Shokat, Kevan M.; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 5483 – 5488;,
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Synthetic Route of 1224944-77-7, 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. 1224944-77-7, name is Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate. A new synthetic method of this compound is introduced below.

A mixture of ethyl 5-chloropyrazolo[1 ,5-a]pyrimidine-3-carboxylate (677 mg, 3.00 mmol), methanamine (3.0 ml, 2.0 M, 6.0 mmol) and N,N-diisopropylethylamine (1.6 ml, 9.0 mmol) in 2-propanol (20 ml) was refluxed for 5 h. Upon cooling, ice water was added and the mixturewas extracted with ethyl acetate (3x). The combined organic phases were filtrated through a silicone filter and concentrated to give the title compound (570 mg).[C-MS (Method 1): R = 0.74 mm; MS (ESIneg): m/z = 219 [M-H]1H-NMR (400 MHz, DMSO-d6) 6 [ppm]: 1.258 (7.44), 1.276 (16.00), 1.293 (7.62), 1.296 (2.96), 1.338 (1.13), 2.902 (6.89), 2.914 (6.83), 4.155 (3.10), 4.173 (9.99), 4.191 (9.82),4.209 (2.93), 6.336 (1.70), 6.355 (1.74), 7.855 (1.41), 7.867 (1.40), 8.126 (5.66), 8.482 (1.60), 8.501 (1.56).

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; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 42754-96-1, 4,6-Dichloro-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, HPLC of Formula: C5H2Cl2N4, blongs to pyrimidines compound. HPLC of Formula: C5H2Cl2N4

4,6-dichloro-lH-pyrazolo[3,4-d]pyrimidine (2, 0.21 g, 1.1 mmol), dihydropyran (DHP) (0.3 mL) and p-TSA (7 mg) were taken up in ethyl acetate (5 mL) to form a mixture and the mixture was stirred at room temperature for 12 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was diluted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate and evaporated to dryness to obtain a crude product. The crude product was purified by column chromatography using 20 % EtOAc-hexane to afford 4,6-dichloro- l- (tetrahydro-2H-pyran-2-yl)-l H-pyrazolo[3,4-d] pyrimidine (3, 0.1 1 g, 36 %). NMR (400 MHz, CDC13): delta 8.25 (s, 1 H), 6.04-6.00 (d, 1H), 4.18-4.13 (m, 1H), 3.85-3.80 (t, 1 H), 2.60-2.58 (m, 1H), 2.17-2.15 (m, 1 H), 1.99-1 .96 (d, 1 H), 1.84-1.82 (t, 2H), 1 .77-1 .76 (d, 1 H).

The synthetic route of 42754-96-1 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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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. 33097-11-9, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbaldehyde, the common compound, a new synthetic route is introduced below. name: 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbaldehyde

To the solution of phosphorus oxy chloride (65 mL, 0.70 mol) in trichloroethylene (46.5 mL) was added DMF (25 mL, 0.32 mol) slowly to keep the temperature between 5 0C to 10 0C. The solution was then warmed up to room temperature before 6-hydroxy-2-(methylthio)-4(lH)- pyrimidinone (25 g, 0.16 mol) was added in portions. The resultant reaction mixture was heated at 80 0C overnight followed by concentration under vacuum. The resulting slurry like residue was poured into ice, stirred for 2 hours then filtered to afford the crude product. The crude product was further purified by recrystalization with hexane to afford 4,6-dichloro-2-(methylthio)-5- pyrimidinecarbaldehyde (21.3 g , 61%). 1H-NMR (CDCl3) delta 2.66 (s, 3 eta), 10.4 (s, 1 eta).To a solution of 4,6-dichloro-2-(methylthio)-5-pyrimidinecarbaldehyde (10.0 g, 44.8 mmol) in TetaF (250 mL) was added 2,6-difluoroaniline (5.35 mL, 49.3 mmol, 1.1 eq) followed by Et3N (12.6 mL, 89.6 mmol, 2 eq). The reaction mixture was heated to 550C for about 22 h before concentrated. The slurry was re-dissolved in DCM (250 mL) and washed with H2O (2 x 100 mL), then concentrated and further washed with acetone (2 x 10 mL) to give 9.87 g (70 %) of pure 4- chloro-6-[(2,6-difluorophenyl)amino]-2-(methylthio)-5-pyrimidinecarbaldehyde. LC-MS m/z 316 (M+H)+.A solution of 4-chloro-6-[(2,6-difluorophenyl)amino]-2-(methylthio)-5- pyrimidinecarbaldehyde (200 mg, 0.63 mmol) in DMF (4.0 mL) and acetic anhydride (2.0 mL) was heated with a microwave (16O0C) for about 30 minutes. The resultant mixture was then concentrated. Flash chromatography (EtOAc / Hexane, 1 : 5) provided the title compound (109 mg, 51%): LC-MS m/z 340 (M+H)+.

The synthetic route of 33097-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/147103; (2007); A2;,
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Reference of 148550-51-0, 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. 148550-51-0, name is Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate, molecular formula is C8H10N2O4S, 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.

A solution of 2-methanesulfonyl-pyrimidine-5-carboxylic acid ethyl ester (0.0434 mol) in acetonitrile is added under nitrogen to a solution of 4-N-(tertbutoxycarbonyl) aminopiperidine (0.0362 mol) and potassium carbonate (0.0724 mol). The mixture was stirred at room temperature for 15 hours, poured out onto ice. The precipitate was filtered, washed with water and DIPE and dried yielding 7.9g of intermediate 4.

According to the analysis of related databases, 148550-51-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2006/122926; (2006); A1;,
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Application of 43212-41-5, Adding some certain compound to certain chemical reactions, such as: 43212-41-5, name is 2,4-Dichloro-6-methoxypyrimidine,molecular formula is C5H4Cl2N2O, 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 43212-41-5.

This product is mixed with morpholine in THF and stirred at 20-25 to give 6-methoxy-2-morpholino-4-chloropyrimidine.

According to the analysis of related databases, 43212-41-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Upjohn; US5120843; (1992); A;,
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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. 26452-81-3, name is 4-Chloro-6-methoxypyrimidine, molecular formula is C5H5ClN2O, 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. Quality Control of 4-Chloro-6-methoxypyrimidine

EXAMPLES 7-12 General Procedure for Conversion of 4-chloro-6-methoxypyrimidine (CMP) to 4,6-dichloropyrimidine (DCP): The reaction vessel is a Morton-type flask fitted with a heating mantle, a mechanical agitator, a temperature probe, a phosgene dip pipe (which also serves as a nitrogen inlet when phosgene is not being introduced to the reactor), and a dry ice condenser. The dry ice condenser is vented into a caustic scrubber. The reactor is charged with CMP, solvent, and catalyst. The agitator is started and the mixture is heated to 100°-110° C. When this temperature range is reached, phosgene gas is introduced subsurface to the reaction mixture via the dip pipe. Phosgene addition is continued over 3-5 hours. During the addition, phosgene escaping the reaction mixture is condensed by the dry ice condenser and returned to the reaction mixture. This reflux of phosgene begins shortly after the phosgene addition is begun, and continues throughout the course of the reaction.

With the rapid development of chemical substances, we look forward to future research findings about 26452-81-3.

Reference:
Patent; Doyle, Timothy John; Wehrenberg, Peter Karl; Standen, Michael Charles Henry; US2002/42514; (2002); A1;,
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