Pyrimidines

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.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, molecular weight is 394.2783, as common compound, the synthetic route is as follows.302964-08-5

Example 10; Procedure for the Preparation of Dasatinib Form FA mixture of compound 1 (0.30 g, 0.76 mmol), N-(2-hydroxyethyl)piperazine (0.49 g, 3.76 mmol) and N-ethyldiisopropylamine (0.26 ml, 1.52 mmol) in dioxane (1.0 ml) was refluxed for 3 hours. The suspension was slowly cooled to 0-5 C. The product was filtered off, washed with dioxane and dried on the filter. Yield: 0.43 g.

Statistics shows that 302964-08-5 is playing an increasingly important role. we look forward to future research findings about 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide.

Reference:
Patent; SIMO, Ondrej; Filipcik, Jiri; Martaus, Alexandr; Jegorov, Alexandr; Gavenda, Ales; Aronhime, Judith; Vraspir, Pavel; Koltai, Tamas; Faustmann, Jiri; Gabriel, Roman; US2009/118297; (2009); A1;,
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213265-83-9, A common compound: 213265-83-9, name is 4,6-Dichloro-5-fluoropyrimidine,molecular formula is C4HCl2FN2, 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.

Intermediate A39-2 (200mg, 1.07mmol) was dissolved in tetrahydrofuran (5mL), was added 4,6-dichloro-5-fluoropyrimidine (179mg, 1.07mmol),Diisopropylethyl amine (414mg, 3.21mmol), 50 stirred overnight, cooled to room temperature, spin dry solvent, the residue was purified by column chromatography (dichloromethane:Methanol = 150: 1) to give a colorless oil (240mg, 71%). 1HNMR (400MHz, CDCl3) delta8.23 (s, 1H), 7.51 (s, 1H),7.45-7.40 (m, 4H), 6.30 (s, 1H), 5.55 (s, 1H), 4.79 (d, J = 6.0Hz, 2H), 3.89 (s, 3H).

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 213265-83-9.

Reference:
Patent; Suzhou Yunxuan Pharmaceutical Co., Ltd.; Zhang, Xiaohu; (54 pag.)CN105254613; (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. 5750-76-5, name is 2,4,5-Trichloropyrimidine. A new synthetic method of this compound is introduced below., 5750-76-5

General procedure: 2-Amino-N-methylbenzamide 10 was prepared according tothe general procedure in literatures 33-35. The prepared 2-amino-N-methylbenzamide 10 (1.00 g, 6.67 mmol) was added inone portion to 2,4,5-trichloropyrimidine (1.22 g, 6.67 mmol) or2,4-dichloro-5-nitropyrimidine (1.29 g, 6.67 mmol) and DIPEA(1.29 g, 10.0 mmol) in isopropanol (100 mL). The resulting mixturewas stirred at 85 C for 6 h. The mixture was evaporated to dryness,and the residue was recrystallised from MeCN/water 20:1to yield 2-(2-chloro-5-substitudedpyrimidin-4-ylamino)-Nmethylbenzamide(1.69 g, 85%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5750-76-5, 2,4,5-Trichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Liu, He; Wu, Bin; Ge, Yang; Huang, Jiaxin; Song, Shijie; Wang, Changyuan; Yao, Jihong; Liu, Kexin; Li, Yanxia; Li, Yongming; Ma, Xiaodong; Bioorganic and Medicinal Chemistry; vol. 25; 24; (2017); p. 6313 – 6321;,
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504-17-6, Adding a certain compound to certain chemical reactions, such as: 504-17-6, 4,6-Dihydroxy-2-mercaptopyrimidine, 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, 504-17-6, blongs to pyrimidines compound.

General procedure: [H2-DABCO][H2PO4]2 (0.065mmol, 0.020 g) was added to a mixture of the aromatic aldehyde (1 mmol), malononitrile (1 mmol) and barbituric or thiobarbituric acid (1 mmol) in water (3 mL). Then the mixture was heated at 75 C while was monitored by TLC (n-hexane:ethyl acetate; 1:9). After completion of the reaction, the mixture was cooled to room temperature and the solid productwas filtered, washed with cold distilled water (2 mL) and was recrystallized from warm ethanol if necessary.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,504-17-6, its application will become more common.

Reference:
Article; Shirini, Farhad; Langarudi, Mohaddeseh Safarpoor Nikoo; Daneshvar, Nader; Journal of Molecular Liquids; vol. 234; (2017); p. 268 – 278;,
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A common compound: 3934-20-1, name is 2,4-Dichloropyrimidine,molecular formula is C4H2Cl2N2, 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., 3934-20-1

To a solution of 2, 4-dichloro-pyrimidine (15-0 g) in THF (150 mL) was added 50% aqueous Me2NH (22.7 g). The mixture was stirred at ambient temperature for 2 hr and poured into saturated aqueous NaHC03. The aqueous layer was extracted with CHC13 (three times). The combined organic layer was dried over MgS04, filtrated, concentrated under reduced pressure, and purified by flash chromatography (NH-silica, 20% EtOAc in hexane) to give (2-chloro-pyrimidin-4-yl)-dimethyl-amine (8.66 g) and (4-chloro- pyrimidin-2-yl)-dimethyl-amine (0.87 g). (2-chloro-pyrimidin-4-yl)-dimethyl-amine; CI MS m/e 158, M + For : 1H NMR (300 MHz, CDC13) 8 3.12 (s, 6 H), 6. 32 (d, J= 6.1 Hz, 1 H), 8.00 (d, J = 6.1 Hz, 1 H). (4-chloro-pyrimidin-2-yl)-dimethyl-amine ; ESI MS m/e 157, M> ;’H NMR (300 MHz, CDCI3) No. 3. 21 (s, 6 H), 6.50 (d, J= 5.1 Hz, 1 H), 8.18 (d, J= 5. 1 Hz, 1 H).

With the rapid development of chemical substances, we look forward to future research findings about 3934-20-1.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; Arena Pharmaceuticals, Inc; WO2005/95357; (2005); A2;,
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147118-37-4, 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. 147118-37-4, name is N-(4-(4-Fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide, molecular formula is C16H18FN3O3S, 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.

EXAMPLE 19 Preparation of 2-methyl-1-phenylpropan-2-yl 2-((4R,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 (3) 2-methyl-1-phenylpropan-2-yl 2-((4R,6S)-2,2-dimethyl-6-((1-phenyl-1H-tetrazol-5-ylsulfonyl)methyl)-1,3-dioxan-4-yl)acetate (25.75 g) prepared in Example 15 and N-(4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide (15.55 g) were dissolved in tetrahydrofuran (60 ml), followed by cooling to -78 C. under an argon atmosphere, and lithium bis(trimethylsilyl)amide (120 of a 0.5M solution in tetrahydrofuran) was added thereto over 10 minutes, followed by stirring at the same temperature for 2 hours. Then, the mixture was stirred for 4 hours while warming to 0 C. A saturated ammonium chloride aqueous solution (250 ml) was added to the reaction liquid, followed by stirring for 10 minutes, and ethyl acetate (500 ml) was added thereto. The organic layer was separated and washed successively with purified water (250 ml), a saturated sodium bicarbonate aqueous solution (250 ml,) and a saturated sodium chloride aqueous solution (250 ml), dried over anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The resulting solid was stirred with isopropyl ether, filtered and collected. This solid was dried in a vacuum oven overnight (50 C., 200 mbar) to give the title compound (26.06 g, 90%). 1H-NMR (400 MHz, CDCl3) delta 7.66-7.63 (m, 2H), 7.29-7.05 (m, 7H), 6.52-6.48 (dd, 1H), 5.48-5.43 (dd, 1H), 4.43-4.37 (m, 1H), 4.32-4.21 (m, 1H), 3.60 (s, 3H), 3.53 (s, 3H), 3.39-3.36 (m, 1H), 3.12-2.99 (dd, 2H), 2.50-2.27 (m, 2H), 1.51-1.37 (m, 14H), 1.28-1.10 (m, 7H)

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. 147118-37-4, N-(4-(4-Fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Lee, Hongwoo; Park, Daejong; Yoo, Choongleol; Nam, Donghyuk; Ryu, Hohyung; Kim, Dongjin; US2012/136151; (2012); A1;,
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74-69-1, 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 74-69-1 as follows.

General procedure: In the vessel of a microwave reactor, 12 (400 mg, 1.13 mmol), 2-aminopyridine (318 mg, 3.38 mmol), Pd2(dba)3 (51.6 mg,56.4 lmol), 2-dicyclohexylphosphino-20,40,60-triisopropyl-1,10-biphenyl (26.9 mg, 56.4 lmol), and K2CO3 (312 mg, 2.25 mmol)were suspended in t-BuOH (3 mL). The vessel was then sealed,and the mixture was reacted at 130 C for 1 h under microwaveirradiation. After cooling to room temperature, the mixture wasextracted with CHCl3/MeOH (4:1), and washed with brine. Theorganic layer was separated, dried over MgSO4, and concentratedunder reduced pressure. The residue was purified by NH silicagel column chromatography (CHCl3/MeOH = 100:0 to 90:10) togive the title compound (362 mg, 78%). 1H NMR (400 MHz,DMSO-d6) d: 1.27-1.38 (2H, m), 1.41 (9H, s), 1.95-2.02 (2H, m),2.96-3.10 (2H, m), 3.43-3.53 (1H, m), 3.80-3.88 (2H, m), 6.83-6.87 (1H, m), 7.07 (1H, br), 7.22 (1H, s), 7.62-7.66 (2H, m), 7.80(1H, br), 8.20-8.22 (1H, m), 8.40 (1H, s), 8.70 (1H, d, J = 7.2 Hz),9.47 (1H, s). MS (ESI) m/z: 413 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis 74-69-1, I believe this compound will play a more active role in future production and life.

Reference:
Article; Nakajima, Yutaka; Aoyama, Naohiro; Takahashi, Fumie; Sasaki, Hiroshi; Hatanaka, Keiko; Moritomo, Ayako; Inami, Masamichi; Ito, Misato; Nakamura, Koji; Nakamori, Fumihiro; Inoue, Takayuki; Shirakami, Shohei; Bioorganic and Medicinal Chemistry; vol. 24; 19; (2016); p. 4711 – 4722;,
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A common compound: 720-01-4, name is Ethyl 4-chloro-2-trifluoromethylpyrimidine-5-carboxylate,molecular formula is C8H6ClF3N2O2, 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., 720-01-4

Example 18 ETHYL 4-HYDRAZINO-2-TRIFLUOROMETHYLPYRIMIDINE-5-CARBOXYLATE A solution of ethyl 4-chloro-2-trifluoromethylpyrimidine-5-carboxylate (0.20 g, 0.79 mmol), hydrazine (0.18 g, 6.0 mmol) and THF was stirred for 1 h at room temperature. The solution was filtered and dried to give the title compound in a 96% yield; 1 H NMR (CDCl3) delta 9.26 (bs, 1H), 8.90 (s, 1H), 4.40 (q, 2H), 4.24 (bs, 2H), 1.41 (t,3H).

With the rapid development of chemical substances, we look forward to future research findings about 720-01-4.

Reference:
Patent; Signal Pharmaceuticals, Inc.; US5935966; (1999); A;,
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Pyrimidine – Wikipedia

90213-66-4, 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 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.

1.0 g of 2,4-dichloro-7H-pyrrole [2,3-d]pyrimidine was dissolved in 50 mL of dichloromethane under ice bath. To the above mixed solution, 1.06 g of p-toluenesulfonyl chloride, 1.08 g of triethylamine, and 0.019 g of 4-dimethylaminopyridine were slowly added. The mixed solution was stirred at room temperature for 5 h. After the reaction was completed, 150 mL of dichloromethane was poured into the above solution, and the organic phase was washed three times with 100 mL of each of water, aqueous citric acid and brine; The organic phase was dried over anhydrous magnesium sulfate (MgSO4). Recrystallization from petroleum ether gave 1.6 g of white pure product. The yield was 89%.

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 90213-66-4, 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; Shandong University; Zhang Yingjie; Liang Xuewu; Xu Wenfang; (47 pag.)CN108864057; (2018); A;,
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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. 591-55-9, name is 5-Aminopyrimidine. A new synthetic method of this compound is introduced below., 591-55-9

General procedure: Ethyl 2-[(2-fluorophenyl)amino]-4-oxo-4,5-dihydrofuran-3-carboxylate. Diethyl malonate (1.0 mL, 6.6 mmol) was addeddropwise to a solution of sodium hydride (60% w/w in oil, 317 mg,7.9 mmol) in anhydrous tetrahydrofuran (12 mL) that was cooledwith ice bath. The mixture was heated at reflux for 6 min. Aftercooling with ice bath, the reaction mixture was treated dropwisewith chloroacetyl chloride (0.58 mL, 7.2 mmol) and stirred in the icebath for 1 h, and then stirred at 45 C for 1 h. The reaction mixturewas cooled in the ice bath again, and then 2-fluoroaniline (0.76 mL,7.9 mmol) was added dropwise. After stirring at ambient temperaturefor 17 h, the reaction mixture was heated at reflux for 2.5 h.The reaction mixture was allowed to cool to ambient temperature,diluted with aqueous saturated sodium bicarbonate solution, andextracted with ethyl acetate twice and with chloroform. Theorganic layerwaswashed with brine, dried over sodium sulfate andconcentrated. The residue was triturated with ethanol-hexane toafford the title compound as a pale yellow solid (0.58 g, 33%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,591-55-9, 5-Aminopyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Irie, Takayuki; Asami, Tokiko; Sawa, Ayako; Uno, Yuko; Hanada, Mitsuharu; Taniyama, Chika; Funakoshi, Yoko; Masai, Hisao; Sawa, Masaaki; European Journal of Medicinal Chemistry; vol. 130; (2017); p. 406 – 418;,
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