Tag: M.W:200-300

Synthetic Route of 70227-50-8 ,Some common heterocyclic compound, 70227-50-8, molecular formula is C8H10ClN3O2, 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 compound 270.1 (1 g, 4.6 mmol, WO2006065703) in MeOH (3 ml) was added triethylamine (1 ml, 2 eq) in a sealed tube and stirred at 80 C for 2 hr. After completion of the starting material (by TLC), the reaction mixture was cooled to room temperature and evaporated under reduced pressure. The crude material was diluted with water (15 ml) and extracted with EtOAc (2×15 ml). The combined organic layers was washed with brine solution and dried over Na2SO^ The solvent was evaporated under reduced pressure to afford compound 270.2 (700 mg, 71%) as yellowish oil. 1H-NMR (CDCl3, 200 MHz): delta 9.12 (s, 1H), 4.18 (s, 1H), 1.41 (s, 9H). LCMS m/z = 212 [M+l].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,70227-50-8, its application will become more common.

Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; CHUAQUI, Claudio; COSSROW, Jennifer; DOWLING, James; GUAN, Bing; HOEMANN, Michael; ISHCHENKO, Alexey; JONES, John, Howard; KABIGTING, Lori; KUMARAVEL, Gnanasambandam; PENG, Hairuo; POWELL, Noel; RAIMUNDO, Brian; TANAKA, Hiroko; VAN VLOTEN, Kurt; VESSELS, Jeffrey; XIN, Zhili; WO2010/78408; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
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Electric Literature of 1235451-38-3 ,Some common heterocyclic compound, 1235451-38-3, molecular formula is C10H14BrN3O2, 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 compound 233-S3 (1.2 equiv) in 1,4- dioxane (10 vol) at 0 C under nitrogen atmosphere was added tert-butyl ((5-bromopyrimidin-2- yl)methyl)carbamate (1 equiv), potassium acetate (3 equiv) and PdCI2(dppf) (0.1 equiv). Thereaction mixture was stirred at 90 0C for 12 hours and concentrated. The residue was purified by column chromatography on silica gel using hexane/EtOAc to afford compound 233-S4.

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. 1235451-38-3, tert-Butyl ((5-bromopyrimidin-2-yl)methyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; BARRISH, Joel, Charles; GREENLEE, William; EASTMAN, Kyle, J.; (0 pag.)WO2018/160889; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
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Application of 85386-20-5, 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.85386-20-5, name is 5-Phenylpyrimidine-2-carboxylic acid, molecular formula is C11H8N2O2, molecular weight is 200.19, as common compound, the synthetic route is as follows.

To a solution of the compound as obtained in Referential Example 3 (10.2 g) in tetrahydrofuran (150 ml), 20% palladium hydroxide-on-carbon (4.19 g) was added in nitrogen atmosphere, followed by an overnight’s stirring in hydrogen atmosphere of one atmospheric pressure. The reaction system was nitrogen-exchanged to suspend the reaction, and the reaction liquid was filtered with Celite. The filtrate was concentrated under reduced pressure. To a solution of the residue in dimethylformamide (70 ml), phenylpyrimidinecarboxylic acid (5.97 g) as obtained in Referential Example 10 and triethylamine (8.3 ml) were added at 0C, followed by further dropwise addition of a solution of 2-chloro-1,3-dimethylimidazolium chloride (6.55 g) in dimethylformamide (30 ml) and subsequent an hour’s stirring. After addition of aqueous sodium hydrogencarbonate solution to the reaction liquid and dilution with water, the formed solid was recovered by filtration. The solid was subjected to silica gel column chromatography (chloroform: methanol = 95:5) and recrystallized from ethyl acetate, to provide the title compound (7.65 g) as yellow crystals. 1H-NMR(400MHz,d6-DMSO,deltappm):1.05-1.08(6H,m), 2.05-2.25(2H,m), 2.78(3/2H,s), 2.96(3/2H,s), 2.82-3.10(1H,m), 3.35-3.55(2H,m), 3.65-3.87(2H,m), 4.78-4.89(1/2H,m), 5.13-5.25(1/2H,m), 6.88-6.93(1H,m), 7.51-7.60(4H,m), 7.90-7.92(3H,m), 8.01(1H,d,J=8.8Hz), 8.36(1H,d,J=2.4Hz), 9.34(2H,s), 10.85(1H,s). ESI-MS Found:m/z 496[M+H]+

The chemical industry reduces the impact on the environment during synthesis 85386-20-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1630162; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 313339-35-4, 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.313339-35-4, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid, molecular formula is C6H4Cl2N2O2S, molecular weight is 239.08, as common compound, the synthetic route is as follows.

(2) To a mixture of 4,6-dichloro-5-carboxy-2-methylthiopyrimidine (prepared in the above (1)) 500 mg and triethylamine 0.58 ml in dimethylformamide 3 ml is added 3-chloro-4-methoxybenzylamine 359 mg in dimethylformamide 3 ml at room temperature over a period of 15 minutes, and the mixture is stirred for 4 hour. The reaction mixture is diluted with a 10% aqueous citric acid solution and extracted with ethyl acetate. The organic layer is washed, dried and concentrated in vacuo to give 4-(3-chloro-4-methoxybenzylamino)-5-carboxy-6-chloro-2-methylthiopyrimidine as a slightly brown powder.

The chemical industry reduces the impact on the environment during synthesis 313339-35-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Yamada, Koichiro; Matsuki, Kenji; Omori, Kenji; Kikkawa, Kohei; US2004/142930; (2004); A1;,
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Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1111237-76-3, name is 5-Bromo-4-chloro-2-methyl-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

b) Preparation of intermediate 152; A solution of intermediate 151 (0.01014 mol) in THF (50 ml) was stirred under N2- flow at -78 0C and a solution of n-BuLi 2.5M (0.0305 mol) in THF (10 ml) was added dropwise. After addition, the reaction was continued for one hour at -78 C. A solution of DMF (0.02029 mol) in THF (10 ml) was added dropwise. The reaction mixture was stirred for 30 min at -78 0C. The reaction mixture was allowed to reach -30 0C, and H2O (10 ml) was added dropwise. The reaction mixture was stirred for 30 min. The organic layer was separated and filtered over silica gel (eluent: THF). The collected fractions were concentrated under reduced pressure and the residue was stirred in a mixture of 2% CH3OH and 98% DCM. The precipitate was filtered off, washed and dried under vacuo, yielding 0.85 g (42.8%) of intermediate 152.

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, 1111237-76-3, 5-Bromo-4-chloro-2-methyl-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WO2009/16132; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 199678-12-1, 4-Pyrimidin-2-yl-benzoic acid, 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, 199678-12-1, blongs to pyrimidines compound. SDS of cas: 199678-12-1

General procedure: Synthesis of amides from the carboxylic acid: A 100 mL round bottom flask was charged with carboxylic acid (11 mmol) to which thionyl chloride (10 mL) was added dropwise under flow of argon at room temperature. The reaction mixture was refluxed for 3 h at 85 C, then the excess SOCl2 was removed in vacuo to afford the crude acid chloride on one hand, whereas in another flask solution of 8-aminoquinoline (10 mmol) and NEt3 (11 mmol) in dichloromethane (20 mL) was stirred for 10-15 minutes. Deprotonated amine was added to a solution of acid chloride at 0 C. The reaction was allowed to warm to room temperature and stirred overnight for complete conversion. Upon completion, it was quenched with saturated NaHCO3 solution and extracted with CH2Cl2 three times. These extracts were combined and dried over NaSO4. After evaporation in vacuum, the crude amide product was purified by flash column chromatography (Hexane: ethyl acetate 10:1) through silica gel.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,199678-12-1, its application will become more common.

Reference:
Article; Kalsi, Deepti; Barsu, Nagaraju; Dahiya, Pardeep; Sundararaju, Basker; Synthesis; vol. 49; 17; (2017); p. 3937 – 3944;,
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Related Products of 114040-06-1 , The common heterocyclic compound, 114040-06-1, name is 3-Bromo-5,7-dichloropyrazolo[1,5-a]pyrimidine, molecular formula is C6H2BrCl2N3, 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 3-bromo-5,7-dichloropyrazolo[l,5-a]pyrimidine (5.0 g, 19 mmol) in DCM (50 mL) was added cyclopropylmethanamine (1.48 g, 21 mmol), and DIPEA (6.6 mL, 38 mmol). The reaction was stirred at rt for 2 h. Water and DCM were added to separate the phases and the aqueous phase was extracted with DCM. The combined organic extracts were dried over NaSC>4, filtered and concentrated. The crude product was purified by flash chromatography (gradient: EtO Ac/hex 0-50%) to give the title compound as a yellow solid (5.25 g, 92%). NMR (400 MHz, CDCl3) delta ppm 7.97 (s, 1H), 6.50 (br. s, 1H), 5.97 (s, 1H), 3.25 (dd, J = 7.3, 5.5 Hz, 2H), 1.26-1.13 (m, 1H), 0.74-0.65 (m, 2H), 0.37 (q, J= 5.0 Hz, 2H); MS ESI [M + H]+ 301.0, calcd for [Ci0Hi0BrClN4 + H]+ 301.0.

The synthetic route of 114040-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; LAUFER, Radoslaw; NG, Grace; LI, Sze-Wan; PAULS, Heinz W.; LIU, Yong; PATEL, Narendra Kumar B.; WO2015/70349; (2015); A1;,
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Pyrimidine – Wikipedia

Application of 53557-69-0, 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. 53557-69-0, name is 6-Iodopyrimidin-4-amine. A new synthetic method of this compound is introduced below.

Step 2: 5-(6-Aminopyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole- 3-carbonitrile (VI)Into a 50 mL round bottom flask equipped with a stir bar, condenser and 3-way valve connected to argon and vacuum 2-(5-chloro-2-methylphenyl)-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1-{[2-(trimethylsilyl)ethoxy] methyl}-1 H-pyrrole-3-carbonitrile coming from the previous step, 6-iodopyrimidin-4-amine (740 mg, 3.35 mmol), 2M Na2C03 (3.35 mL, 6.70 mmol) and dioxane (22 mL) were charged at room temperature. The resulting reaction mixture was degassed three times back filling with argon each time before being charged PdC (dppf) (182 mg, 0.223 mmol). The resulting reaction mixture was degassed four times back filling with argon each time and then warmed to 110 C for 1 h. The reaction mixture was cooled to room temperature, filtered through a pad of Celite, washed with EtOAc, and the filtrate was concentrated and then diluted with EtOAc (30 mL) and water (10 mL). The two layers were separated, and the aqueous layer was extracted with EtOAc (25 mL). The combined organic fractions were washed with aqueous brine (2 x 20 mL), dried over a2S04, filtered and concentrated under reduced pressure. The residue was purified by Biotage SP1 Flash Chromatography (DCM/MeOH/7N NH3in MeOH 97/2/1) to afford the title compound (343 mg, 35%, 2 steps)..

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,53557-69-0, its application will become more common.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; BRASCA, Maria Gabriella; BINDI, Simona; CALDARELLI, Marina; NESI, Marcella; ORRENIUS, Sten Christian; PANZERI, Achille; WO2014/19908; (2014); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 1266343-30-9, name is 5-Bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C7H5BrClN3

Stir a suspension of 5-bromo-4-chloro-7-methyl-pyrrolo[2,3-d]pyrimidine (454 g 1.84 mol) in ammonia (30% in H20, 3.63 L) at 120 C in a Hastelloy pressure vessel for 18 h. Cool to 20 C, filter, wash with H20 (1.80 L) and methanol (900 mL), and dry to give the title compound (351 g, 82%) as a white solid. ES/MS m/z (79Br) 227.2(M+H).

With the rapid development of chemical substances, we look forward to future research findings about 1266343-30-9.

Reference:
Patent; ELI LILLY AND COMPANY; CIFUENTES-GARCIA, Marta Maria; GARCIA-PAREDES, Maria Cristina; (34 pag.)WO2018/194885; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 83255-86-1 ,Some common heterocyclic compound, 83255-86-1, molecular formula is C5H4BrN5, 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.

Add N, N-dimethylacetamide (50mL) to the reaction flask,Add 4-phenoxybenzoic acid (II) (4.81g, 0.022mol) under nitrogen protection,3-bromo-4-amino-1H-pyrazolo [3,4, d] pyrimidine (III) (4.37 g, 0.02 mol),Sodium carbonate (8.74g, 0.1mol), CuBr (0.43g, 0.003mol), 1,10-phenanthroline (0.73g, 0.004mol). The temperature was raised to 150 C for 24h. The temperature was lowered to room temperature, water was slowly added to precipitate a solid, filtered, and dried to obtain a solid product (4.95 g, yield: 81.5%).

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. 83255-86-1, 3-Bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hangzhou China-USA East China Pharmaceutical Co., Ltd.; Yu Rui; Chen Yu; Wu Honghui; Hu Haiwen; Ye Kai; (6 pag.)CN110511225; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia