Tag: M.W=300-400

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., category: pyrimidines

Synthesis of 1-isopropyl-3-(2,3-dimethoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (BA65); A solution 2,3-dimethoxyphenylboronic acid (105 mg, 0.58 mmol) in EtOH (3.3 ml) was added to a solution of 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (70 mg, 0.23 mmol) in DME (12 ml). Pd(PPh3)4 (30 mg, 0.03 mmol) and saturated Na2CO3 (1.9 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 silica gel column chromatography [MeOH-CH2Cl2, 2:98] to yield BA65 (63 mg, 88% yield). ESI-MS (M+H)+ m/z calcd 314.1, found 314.1.

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 153435-63-3, Adding some certain compound to certain chemical reactions, such as: 153435-63-3, name is 2-(Tributylstannyl)pyrimidine,molecular formula is C16H30N2Sn, 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 153435-63-3.

A solution of the product from step 1 (1.74 g, 7.87 mmol), 2-(tributylstannyl)pyrimidine (4.36 g, 11.81 mmol), CsF (4.78 g, 31.5 mmol), and copper(I) iodide (0.450 g, 2.36 mmol) in DMF (16 mL) in a pressure vessel was sparged with nitrogen and treated with Pd(PPh3)4 (0.455 g, 0.394 mmol). The mixture was sealed and heated at 120 C overnight. The cooled reaction mixture was partitioned between EtOAc and water and filtered through celite. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-30% EtOAc in hexanes), to provide the title compound as a yellow solid. LRMS m/z (M+H) 221.2 found, 221.1 required.

According to the analysis of related databases, 153435-63-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIVERTON, Nigel; BESHORE, Douglas, C.; KUDUK, Scott, D.; LUO, Yunfu; MENG, Na; YU, Tingting; WO2015/20930; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 153435-63-3, 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. 153435-63-3, name is 2-(Tributylstannyl)pyrimidine. A new synthetic method of this compound is introduced below.

Description 28: methyl 6-methyl-3-(2-pyrimidinyl)-2-pyridinecarboxylate (D28); To a suspension of methyl 3-iodo-6-methyl-2-pyridinecarboxylate D27 (300 mg), CsF (329 mg, 2.166 mmol) and Pd(Ph3P)4 (50.0 mg, 0.043 mmol) in DMF (10 ml) stirred under nitrogen at room temperature, was added 2-(tributylstannanyl)pyrimidine (480 mg, 1.299 mmol). The reaction mixture was stirred at 130 0C for 30 minutes in a microwave Personal Chemistry. The reaction mixture was partitioned between EtOAc and aqueous NaHCO3 saturated solution; the combined organic phases were dried to give the crude product, which was purified by silica gel chromatography (SNAP KP-NH 55 g; Cy/EtOAc from 100:0 to 70:30). Collected fractions were evaporated to obtain the title compound D28 (101 mg) as white solid. UPLC (Basic GEN_QC): rt = 0.56 minutes, peak observed: 230 (M+l). C12H11N3O2 requires 229. 1H NMR (400 MHz, DMSO-J6) delta ppm 8.92 (d, 2 H), 8.49 (d, 1 H), 7.44 – 7.63 (m, 2 H), 3.75 (s, 3 H), 2.57 (s, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153435-63-3, 2-(Tributylstannyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; AMANTINI, David; DI FABIO, Romano; WO2010/122151; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 934524-10-4, 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 934524-10-4, name is 2,4-Dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A solution of 2,4-dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine (0.35g, 1.0 mmol), D-alaninol (0.10 mL, 1.3 mmol) and TEA (0.20 mL, 1.4 mmol) in dioxane (6 mL) was stirred at 7O0C for 20 h. Water and EtOAc were added. The organic phase was washed with IN HCl, then with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give (R)-2-(2-chloro-7- tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)propan-l-ol (0.38 g).

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 934524-10-4, 2,4-Dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; WO2009/131687; (2009); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 330786-24-8, Adding some certain compound to certain chemical reactions, such as: 330786-24-8, name is 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine,molecular formula is C17H13N5O, 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 330786-24-8.

9g tri-n-butylphosphine dissolved in 100mL anhydrous tetrahydrofuran and cooled down to 0-5 degrees.9g of diisopropyl azodicarboxylate was added dropwise under N2 protection. After the addition was completed,The reaction temperature was controlled at 0-5 degrees for 1 h. The above tributylphosphine andA mixture of diisopropyl azodicarboxylate was slowly poured into 4 g of solution3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine andIn 3.5 g of (S)-1-Boc-3-hydroxypiperidine in 50 mL of anhydrous tetrahydrofuran,Stir 0-5 degrees overnight. After the reaction liquid is concentrated under reduced pressure,Purification by column to obtain the product 6.8g, yield 75%

According to the analysis of related databases, 330786-24-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Fupu Biological Technology Co., Ltd.; Liu Zheng; (13 pag.)CN106279284; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 374930-88-8, name is tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate, molecular formula is C13H19BrN4O2, 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. SDS of cas: 374930-88-8

To a solution of dicyclohexylamine (3.43 g, 18.94 mmol) in THF (60 mL) at -78 C. was added n-BuLi (2.5 M, 7.9 mL, 18.94 mmol) dropwise. The mixture was stirred at RT for 10 min, followed by the addition of methyl 2-(4-fluorophenyl)acetate (2.69 g, 16.02 mmol) in toluene (60 mL). After stirred at RT for another 10 min, tert-butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate (5.0 g, 14.57 mmol), Pd2(dba)3 (667 mg, 0.728 mmol) and P(t-Bu)3 (10%, 1.47 g, 0.728 mmol) were added sequentially. The reaction mixture was stirred at RT for 15 h, quenched by water (150 mL) and extracted with EA. The combined organic layers were washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was passed a column (silica gel, PE_EA=6:1) to afford the title compound (0.5 g, 8%) as an orange solid. MS (ES+) C22H27FN4O4 requires: 430. found: 431 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 374930-88-8.

Reference:
Patent; Hodous, Brian L.; Kim, Joseph L.; Wilson, Kevin J.; Wilson, Douglas; Zhang, Yulian; US2015/111887; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 330794-31-5, 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 330794-31-5, name is 1-Cyclopentyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

Example 92 3-[3-(Benzyloxy)phenyl]-1-cyclopentyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine To a mixture of 1-cyclopentyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.200 g, 0.631 mmol, 1 equiv) and 3-(benzyloxy)phenylboronic acid (0.110 g, 0.487 mmol, 1.0 equiv) in DME (6 mL) was added tetrakis(triphenylphosphine)palladium (0.044 g, 0.038 mmol, 0.07 equiv) and a solution of sodium carbonate monohydrate (0.187 g, 1.51 mmol, 2.4 equiv) in water (2 mL). The mixture was heated at 85 C. for 16 h, then allowed to cool to ambient temperature. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc (50 mL) and water (50 mL). The organic layer was dried over MgSO4, filtered, and concentrated to afford an oily red-orange solid. Recrystallization from hot EtOAc afforded a red-orange solid which was purified by preparative RP-HPLC (Rainin C18, 8 mum, 300 A, 25 cm; 10%-60% acetonitrile-0.1M ammonium acetate over 20 min, 21 mL/min). The acetonitrile was removed in vacuo and the aqueous mixture was lyopholyzed to afford 3-[3-(benzyloxy)phenyl]-1-cyclopentyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine as a whitesolid (0.023 g, 0.060 mmol): 1H NMR (d6 CDCl3, 400 MHz): deltaH 8.34 (1H, s), 7.27-7.46 (8H, m), 7.07-7.10 (1H, m), 5.63 (2H, bs), 5.31 (1H, quint, J=7.6 Hz), 5.16 (2H, s), 2.15-2.20 (4H, m), 1.96-2.01 (2H, m), 1.72-1.75 (2H, m); RP-HPLC (Hypercil C18, 5 mum, 100 A, 15 cm; 5%-100% acetonitrile-0.1M ammonium acetate over 15 min, 1 mL/min) Rt 14.00 min. MS: MH+ 386.

According to the analysis of related databases, 330794-31-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Abbott Laboratories; US2002/156081; (2002); A1;,
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. 58536-46-2, name is 4-(4-Bromophenyl)-2,6-diphenylpyrimidine. A new synthetic method of this compound is introduced below., category: pyrimidines

Under an Ar gas atmosphere, the intermediate body X3 (4.8 g, 10 mmol), the intermediate body X7 (3.9 g, 10 mmol), an aqueous solution of 2M sodium carbonate (12 ml), toluene (20 ml), DME (20 ml) and Pd(PPh3)4 (0.35g) were stirred for 16 hours at a reflux temperature. After the reactant solution was cooled down to the room temperature, toluene (200 ml) and water (100 ml) were added thereto to separate an organic phase. The residue obtained by concentrating the organic phase was refined by silica-gel column chromatography (a developing solvent: hexane-toluene) and was recrystallized by toluene twice to provide a target object (a compound No. 4) as a white solid. A yield of the compound No. 4 was 2.6 g and a yield rate thereof was 35%. FD mass analysis consequently showed that m/e was equal to 741 while a calculated molecular weight was 741

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, 58536-46-2, 4-(4-Bromophenyl)-2,6-diphenylpyrimidine.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; EP2489664; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia