Tag: M.W=300-400

Reference of 330786-24-8 ,Some common heterocyclic compound, 330786-24-8, molecular formula is C17H13N5O, 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.

6) Add IM6 (4.5 g, 0.015 mol) in sequence to a 250 mL three-necked flask. N-Boc Hydroxylpiperazine (3.6 g, 0.018 mol), Triphenylphosphine (7.9 g, 0.03 mol) and tetrahydrofuran (45 mL) were cooled in an ice bath. DIAD (6.1 g, 0.03 mol) was added dropwise with stirring. The temperature was controlled to not exceed 20 degrees Celsius. After the addition was complete, the mixture was stirred at room temperature for about 5 hours. Add 45 mL concentrated hydrochloric acid to the reaction flask and stir at room temperature for about 5 h. The tetrahydrofuran was concentrated and removed, poured into 150 mL of water and washed with dichloromethane. The aqueous layer was adjusted to neutral pH with potassium carbonate and extracted with dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to give IM7 (4.0 g , 69%).

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. 330786-24-8, 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nanjing Yi Hua Pharmaceutical Co., Ltd.; Yuan Jing; Liu Wu; Zhang Xia; (7 pag.)CN107641123; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 862730-04-9, 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.

Synthesis of 3-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-N-(4,5-dihydrothiazol-2-yl)benzamide (BA30); A solution of [3-((4,5-dihydrothiazol-2-yl)carbamoyl)phenyl]boronic acid (19 mg, 0.08 mmol) in EtOH (3.3 ml) was added to a solution of 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (20 mg, 0.07 mmol) in DME (12 ml). Pd(PPh3)4 (16 mg, 0.014 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 RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA30 (17.8 mg, 67% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,862730-04-9, 3-Iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; Regents of the University of California; US2007/293516; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 139756-21-1, Adding some certain compound to certain chemical reactions, such as: 139756-21-1, name is 5-(2-Ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one,molecular formula is C17H20N4O2, 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 139756-21-1.

To the chlorosulphonic acid (3.0mL, 36.58mmol) was added 5-(2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one (1g, 2.4mmol) while maintaining the temperature 0C, then reaction was allowed to proceed at 0-5C until TLC analysis indicated the absence of starting material. After completion, to the reaction mixture, cold CHCl3 was added and to it ice was added in portions. Organic layer was separated and re-extracted the water layer with 2×100mL cold CHCl3 and the combined organic layer are washed with brine solution, concentrated under vacuum; Yield 75%.

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. 139756-21-1, 5-(2-Ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Reddy, G. Lakshma; Dar, Mohd. Ishaq; Hudwekar, Abhinandan D.; Mahajan, Priya; Nargotra, Amit; Baba, Adil Manzoor; Nandi, Utpal; Wazir, Priya; Singh, Gurdarshan; Vishwakarma, Ram A.; Syed, Sajad Hussain; Sawant, Sanghapal D.; Bioorganic Chemistry; vol. 89; (2019);,
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Reference of 330786-24-8, 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 330786-24-8 as follows.

[0143] To a stirred solution of 1-2 (0.15 g, 0.5 mmol) inDMF (3.0 mL) 1-12 (0.2 g, 0.54 mmol) and Cs2C03 (0.32 g,1.0 mmol) is added. The reaction mixture is heated to 60 C. After 18 hours, the reaction mixture is concentrated in vacuoand purified via Combi-flash chromatography on silica gel(using a solvent gradient of 5% MeOH in CH2Cl2 ) to afford1-13 (0.18 g, 73%). The following intermediate was preparedin similar fashion:

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,330786-24-8, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOSANAC, Todd; DISALVO, Darren; HORAN, Joshua Courtney; LIANG, Shuang; ZINDELL, Renee M.; US2014/275014; (2014); A1;,
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Pyrimidine – Wikipedia

Reference of 302964-08-5, 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. 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, 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.

iV-(2-chloro-6-methylphenyl)-2-(2-methyl-6-(pyridm-3-yl)pyrimidin-4- ylamino)thiazole-5-carboxamideTo 2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6- methylphenyl)thiazole-5-carboxamide (30mg, 0.076mmol) THF (2.OmL) was added pyridin-3-ylboronic acid (11.2 mg, 0.091mmol), Pd(PPh3)4 (21.2 mg, 0.018 mmol) and Na2CO3 (2 M, 0.15 mL, 0.3mmol). The mixture was stirred under Argon for 5 min, and then the mixture was heated at 160 0C in microwave reactor for Ih. The reaction was cooled to room temperature and water was added, extracted with 10% MeOH in CHCl3 (3*20 mL). The organic layers was combined and concentrated under reduced pressure. The crude was purified with prep-HPLC to obtain the title compound as a yellow solid. LC-ESIMS observed [M+H]+ 437.2 ; 1H NMR (400 MHz, DMSO-d6) delta 12.25 (broad s, IH), 10.01 (s, IH), 9.24 (s, IH), 8.78 (d, J= 5.2 Hz, IH), 8.48 (d, J= 8.0 Hz, IH), 8.33 (s, IH), 7.70-7.67 (m, IH), 7.42-7.41 (m, 2H), 7.32-7.25 (m, 2H), 2.71 (s, 3H), 2.26 (s, 3H).

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 302964-08-5, 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide.

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

A solution of Pd(PPh3 )2C12 (0.073 g, 0.12 mmol), 7 (0.19 g, 1.3 mmol), 8 (0.40 g, 1.2 mmol), and triethylamine (0.5 mL, 3.5 mmol) in DMF (5 mL) was purged for 5 min with argon and added CuI (0.022g, 0.12 mmol). The reaction mixture was heated for Ih at 80 0C and cooled to room temperature. The resulting mixture was concentrated and purified by silica gel chromatography (hexanes/EtOAc 100:0 to 90:10 gradient) to afford the title compound as a yellow solid (0.35 g, 67%).[0161] 1H NMR (500 MHz, DMSO-J6): delta 1.29 (d, J= 6.9 Hz, 6H), 2.38 (s, 3H), 3.47 (qn, J = 6.8 Hz, IH), 7.01 (d, J = 4.1 Hz, IH), 7.32 (t, J = IA Hz, IH), 7.47 (t, J = 1.6 Hz, IH), 7.50 (d, J = 8.4 Hz, 2H), 7.53 (d, J = 1.1 Hz, IH), 7.73 (d, J = 7.8 Hz, IH), 8.04 (d, J = 8.4 Hz, 2H), 8.12 (d, J = 4.0 Hz, IH) [0162] MS (ES+): m/z 450 (M+H)+

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

Reference:
Patent; TARGEGEN INC.; WO2009/55674; (2009); A1;,
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. 428854-24-4, name is 2-(1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidine-4,5,6-triamine, molecular formula is C17H15FN8, 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. Recommanded Product: 2-(1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidine-4,5,6-triamine

Acetone (SO ml) was added to 2-(l-(2-fluorobenzyl)-1H-pyrazo]o[3,4-b]pyridin-3-yl) pyrimidine-4,S,6-triamine (10 gms) compound of formula-2 at 25-30C and stirred for 10 minutes at the same temperature. Dimethyl sulfate (10.79 gms) was slowly added to the reaction mixture at 25-30C and stirred for 40 hours at the same temperature. Filtered the precipitated solid, washed with acetone and dried to get the title compound. Yield: 8 gms.

With the rapid development of chemical substances, we look forward to future research findings about 428854-24-4.

Reference:
Patent; MSN LABORATORIES PRIVATE LIMITED, R&D CENTER; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; VENKATA PANAKALA RAO, Gogulapati; RAJESHWAR REDDY, Sagyam; BALA NARSAIAH, Eppaturi; SRINIVASULU, Rangineni; (32 pag.)WO2018/96550; (2018); A1;,
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Electric Literature of 131860-97-4, 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. 131860-97-4, name is (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate. A new synthetic method of this compound is introduced below.

Embodiment 20 (0104) This embodiment is provided to describe the method for preparing the azoxystrobin compound represented by formula (4) in a one-pot approach in the present invention. (0105) Under nitrogen protection, add 0.1 mol 4,6-dichloropyrimidine, 0.015 mol anhydrous potassium carbonate, 0.15 mol methyl formate, and 0.002 mol 2-methyl-1,4-diazabicyclo[2.2.2]-octane into 100 mL dimethyl benzene solution of 0.1 mol 3-(alpha-methoxy)methylene benzofuran-2-(3H)-ketone sequentially, start stirring, cool down to 5 C., and then control the temperature at 5-20 C., add 5 mL 29 wt. % methanol solution of sodium methoxide in droplets within 60 min., and then let the reaction proceed for 30 min. while stirring, to obtain a solid-containing mixture. Measured by GC, the content of the mixture of methyl 2-(2-((6-chloropyridinyl-4-)oxy)phenyl)-3,3-dimethoxyacrylate and methyl (E)-2-{2-[6-chloropyrimidinyl-4-oxy]phenyl}-3-methoxyacrylate is 92%; measured by LC, the ratio of methyl 2-(2-((6-chloropyridinyl-4-)oxy)phenyl)-3,3-dimethoxyacrylate to methyl (E)-2-{2-[6-chloropyrimidinyl-4-oxy]phenyl}-3-methoxyacrylate is 76:24. Next, distill out methyl formate and methanol under negative pressure; after the end of desolventizing under negative pressure, add 50 g water into the reaction bulb, stir so that the solid is dissolved, keep the solution still for stratification, and then condense the organic phase, to obtain viscous liquid. Add 0.003 mol dimethyl sulfate and 0.1 mol acetic anhydride into the obtained viscous liquid, heat up to 105 C., keep at the temperature and reflux, and let the reaction proceed for 60 min. Measured by GC, the content of the mixture of methyl 2-(2-((6-chloropyridinyl-4-)oxy)phenyl)-3,3-dimethoxyacrylate and methyl (E)-2-{2-[6-chloropyrimidinyl-4-oxy]phenyl}-3-methoxyacrylate is 91%; measured by LC, the ratio of methyl 2-(2-((6-chloropyridinyl-4-)oxy)phenyl)-3,3-dimethoxyacrylate to methyl (E)-2-{2-[6-chloropyrimidinyl-4-oxy]phenyl}-3-methoxyacrylate is 1.0:99; condense the reaction liquid under negative pressure to remove the solvent, to obtain viscous liquid compound methyl (E)-2-{2-[6-chloropyrimidinyl-4-oxy]phenyl}-3-methoxyacrylate. (0106) Add 80 ml butyl acetate, 0.085 mol 2-cyanophenol, 0.095 mol anhydrous potassium carbonate, and 0.003 mol 2,6-dimethyl-1,4-diazabicyclo[2.2.2]-octane into the obtained viscous liquid above, heat up the reaction mixture to 100 C. while stirring, keep at the temperature and let the reaction proceed for 250 min., and monitor the reaction situation with a gas chromatograph (GC). When the GC indicates that the normalized area of methyl (E)-2-[2-(6-chloropyrimidinyl-4-oxy)phenyl]-3-methoxyacrylate is smaller than 1%, add 50 ml water into the reaction system, stir for 10 min., keep the solution still for 10 min. at 80 C. for stratification, and then remove the aqueous phase, and repeat washing the organic phase once by adding water again; cool down the obtained organic phase to -5 C., so that crystals precipitate; then, filter to obtain a wet filer cake of azoxystrobin, rinse the filter cake with butyl acetate, and heat up the rinsed filter cake to approx. 50-60 C. with 50 ml methanol, beat and wash; then, filter and dry; thus, 28.1 g (0.0697 mol) light yellow solid is obtained, the purity is 99.6%, and the yield ratio is 69.7%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,131860-97-4, (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, and friends who are interested can also refer to it.

Reference:
Patent; NUTRICHEM COMPANY LIMITED; SHANGYU NUTRICHEM CO., LTD.; CHEN, Jianwei; WANG, Wenjun; CHI, Jianhong; ZHAO, Yongchang; DENG, Xufang; WANG, Long; JIN, Wentao; CHEN, Guobin; (15 pag.)US2016/200687; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1231930-42-9, 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. 1231930-42-9, name is 6-(2-Chloro-5-fluoropyrimidin-4-yl)-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole, molecular formula is C15H13ClF2N4, 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.

Under nitrogen, 118 mg of N1-(2-dimethylaminoethyl)-5-methoxy-N1-methyl-2-nitro-1,4-phenylenediamine,140 mg of 6-(2-chloro-5-fluoropyrimidin-4-yl)-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole,282 mg of Cs2CO3, 120 mg of Pd2(dba)3 and 108 mg of BINAP were dissolved in 20 ml of 1,4-dioxane, and the mixture was heated at 140 C for 3 h.The insoluble matter in the reaction liquid was cooled and filtered, and the filter cake was washed with dichloromethane, and the filtrate was evaporated to dryness under reduced pressure.Obtaining N1-(2-dimethylaminoethyl)-N4-(5-fluoro-4-(4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole-6-yl) Pyrimidine-2-yl)-5-methoxy-N1-methyl-2-nitro-1,4-phenylenediamine 80 mg as a reddish brown solid.

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 1231930-42-9, 6-(2-Chloro-5-fluoropyrimidin-4-yl)-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole.

Reference:
Patent; WISDRUG INNOCATION PHARMACY RES BEIJING CO LTD; Wentao Chuangxin Pharmaceutical (Beijing) Co., Ltd.; ZHU XIZHEN; Zhu Xizhen; DENG CHENGJUN; Deng Chengjun; ZHOU ZHONGXIANG; Zhou Zhongxiang; (17 pag.)CN107827875; (2018); 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. 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, 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. name: 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

2-oxa-6-azaspiro [3.4] octane (62, 50 mg, 0.44 mmol) was added to a solution of 2 – ((6-chloro-2-methylpyrimidin-4-yl) amino ) (-N, 2-chloro-6-methylphenyl) thiazole-5-carboxamide (52,158 mg, 0.4 mmol) and N, N-diisopropylethylamine (0.14 mL, 0.8 mmol) 1, 4-dioxane (5 mL), heated to reflux, reacted overnight, and TLC monitored the disappearance of the starting material.The reaction was stopped at room temperature and the solvent was removed. The resulting solid was washed twice with methanol and diethyl ether and separated by high performance liquid chromatography to give a pale yellow solid (10 mg, yield 5.3%)

With the rapid development of chemical substances, we look forward to future research findings about 302964-08-5.

Reference:
Patent; Fudan University; Dong, Xiaochun; Zhao, WeiLi; Zhao, Yichao; Lin, Zhaohu; Lu, Xiuhong; Wang, Wen; Dong, Qian; (12 pag.)CN104151321; (2016); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia