Day: November 10, 2020

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

2-(isopropylsulfonyl)aniline (1g, 5.02mmol) and 2,4,5-trichloropyrimidine (1.1g, 6mmol) was dissolved in N,N-dimethylformamide (30 mL) and added sodium hydride (content 60%, 0.4g, 10mmol) then reacted at 25C for 12 hours. Water (20mL) was added then extracted with ethyl acetate (30mL ¡Á 3). The organic phases were combined, washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated in vacuo. The crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 25: 1) gave the product (0.8g, 46% yield).

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:
Patent; Shandong Xuanzhu Pharma Co., Ltd.; Wu, Yongqian; (28 pag.)CN105524045; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

302964-08-5, 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. 302964-08-5, name is 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide. A new synthetic method of this compound is introduced below.

N-(2-chloro-6-methylphenyl)-2-(2-methyl-4,5′-bipyrimidin-6-ylamino)thiazole-5- carboxamideTo 2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6- methylphenyl)thiazole-5-carboxamide (250 mg, 0.634 mmol) in dioxane (10 mL) was added pyrimidin-5-ylboronic acid (94 mg, 0.759 mmol), PdCl2(PPh3)2 (89 mg, 0.127 mmol) and Na2CO3 (2 M, 1 mL, 1.902 mmol). The mixture was stirred under Argon overnight in an oil bath (12O0C). The reaction mixture was cooled to room temperature and water was added, extracted with 10% MeOH in CHCl3 (3×50 mL). The organic layers were washed with brine and dried over anhydrous Na2SO4. The solvent was removed and the crude was purified with preparative HPLC (ACN/ 0.1 % TFA in water) to obtain the title compound as a yellow solid (180 mg, 52%). 1H-NMR (400 MHz, d6-DMSO) delta 12.31 (br s, IH), 10.02 (s, IH), 9.36 (s, 2H), 9.35 (s, IH), 8.34 (s, IH), 7.43 (s, IH), 7.41 (d, J= 1.6 Hz, IH), 7.32-7.25 (m, 2H), 2.71 (s, 3H), 2.26 (s, 3H); MS (m/z): 438.2 [M+l]+.

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. 302964-08-5, 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LIANG, Congxin; KOENIG, Marcel; HE, Yuanjun; WO2008/150446; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Some common heterocyclic compound, 137234-74-3, molecular formula is C6H6ClFN2, 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.137234-74-3

In a 500 mL three-necked flask, 150 mL of dichloroethane was added, 34.1 g of the chlorinated product prepared in the same manner as in the above step (3)1.5 g of azobisisobutyronitrile(AIBN) 28.4 g of N-bromosuccinimide(NBS) was dissolved in 50 mL of dichloroethane, Then drop into the reaction bottle, add dichloroethane 50mL. After the reaction solution was clarified, a mixed solution of 22.1 g of NBS dissolved in 100 mL of dichloroethane was added dropwise, and the mixture was heated to 50 C and reacted for 15 h. After the completion of the reaction, 100 mL of water was added to separate the aqueous phase and the organic phase. The aqueous phase was extracted with 80 mL of dichloroethane and the organic layers were combined. The organic layer was washed with sodium bisulfite solution and the organic layer was washed with water The organic layer was dried over anhydrous sodium sulfate,The solvent dichloroethane was distilled off under reduced pressure to obtain 52.6 g of the target compound 4-(1-bromoethyl)-5-fluoro-6-chloropyrimidine as a pale yellow liquid in a yield of 92%, and the purity of the high performance liquid chromatography was 86% .

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 137234-74-3.

Reference:
Patent; JUHUA Group Technology Center; YANG, JIANRONG; GE, CHENGSHENG; LI, JIAN; (8 pag.)CN103896855; (2016); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

156-81-0, 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 156-81-0 as follows.

2-(3-Fluoro-phenyl)-imidazo[1,2-a]pyrimidin-7-ylamine 2-Bromo-1-(3-fluorophenyl)ethanone (10.9 g, 50 mmol) was added to a solution of 2,4-diaminopyrimidine (3.70 g, 34 mmol) in acetone (185 ml), and the mixture was heated to reflux for 6 h. The cooled suspension was filtered and the precipitate was washed with acetone (50 ml). The solid was re-suspended in water (35 ml) and NH4OHaq. (25%, 50 ml), then it was collected over a glass fiber paper and the filtrate was washed with H2O (75 ml). After drying under vacuum, the product was obtained (5.56 g, 72%) as a yellow solid. MS (m/z)=229.1 [M+H+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,156-81-0, its application will become more common.

Reference:
Patent; Alvarez Sanchez, Ruben; Bleicher, Konrad; Flohr, Alexander; Gobbi, Luca; Groebke Zbinden, Katrin; Koerner, Matthias; Kuhn, Bernd; Peters, Jens-Uwe; Rudolph, Markus; US2011/237564; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
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. 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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia