Day: June 11, 2021

Application of 38696-21-8, 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. 38696-21-8, name is 5-Bromo-N,N-dimethylpyrimidin-2-amine. A new synthetic method of this compound is introduced below.

A mixture of 0.5 g (2.48 mmol) 5-bromo-N,N-dimethyl-pyrimidin-2-amine, 0.8 g (3.24 mmol) bis(pinacolato)diborone, 0.6 g (6.38 mmol) KOAc, 0.2 g (0.25 mmol) (0358) Pd(dppf)CI2 * DCM and dioxane is heated to 100C for 4.5 h. After cooling to RT, the reaction mixture is filtered through a pad of Celite and evorated, water is added and the mixture is extracted with EtOAc. The organic phases are pooled, dried and evaporated The crude product is purified by FC. (0359) Yield: 0.6 g (96%), ESI-MS: m/z = 250 (M+H)+, Rt(HPLC): 0.22 min (HPLC-A)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,38696-21-8, 5-Bromo-N,N-dimethylpyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BLUM, Andreas; GODBOUT, Cedrickx; HEHN, Joerg, P.; PETERS, Stefan; (74 pag.)WO2017/194453; (2017); A1;,
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 13162-26-0, name is 2,4-Dichloro-6-methyl-5-nitropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C5H3Cl2N3O2

Step A: 4-(4-bromo-2,6-dimethylphenylthio)-2-chloro-6-methyl-5-nitropyrimidine; A solution of LiHMDS in THF (77 mmol) is added to a mixture of 4-bromo-2,6-dimethylbenzenethiol (70 mmol) in THF (100 ml) at -78 C. over 15 minutes and the mixture stirred for an additional 2 hours. The mixture is cooled with liquid nitrogen to around -100 C. and a solution of 2,6-dichloro-4-methyl-5-nitropyrimidine (84 mmol) in THF (50 ml) is added rapidly. The reaction is maintained at around -100 C. for 1 hour and then allowed to warm to room temperature. The mixture is filtered and the isolated solid washed with ethanol. The filtrate may be concentrated and crystallized to obtain additional compound.

With the rapid development of chemical substances, we look forward to future research findings about 13162-26-0.

Reference:
Patent; Ardea Biosciences; US2009/162319; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 14048-15-8, 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. 14048-15-8, name is 2,4-Dimethoxypyrimidin-5-amine. A new synthetic method of this compound is introduced below.

To a 250 mL sealed tube equipped with magnetic stirring bar, compounds C-4A (12.48 g, 50 mmol, 1 eq), C-7A (7.76 g, 50 mmol, 1 eq) and C-6E (9.06 g, 50 mmol, 1 eq) were added followed by AcOH (100 mL), and the tube was tightly closed with plastic stopper. The mixture was heated up to 80 C (temperature of the heating bath) and stirred at this temperature overnight. After that time UPLCMS analysis showed almost full consumption of starting materials (which equals to 40 % of a product peak area). The reaction mixture was cooled to room temperature and AcOH was evaporated to dryness. The residue was preadsorbed onto silicagel and purified by chromatography (50 % of AcOEt/n-hexane). After removing of solvents product C-8.C7 was obtained as a dark brown solid/foam (7.63 g, 24.9 % yield, 84 % of purity according to UPLCMS analysis.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14048-15-8, its application will become more common.

Reference:
Patent; Adamed sp. z o.o.; FEDER, Marcin; MAZUR, Maria; KALINOWSKA, Iwona; JASZCZEWSKA, Joanna; LEWANDOWSKI, Wojciech; WITKOWSKI, Jakub; JELEN, Sabina; WOS-LATOSI, Katarzyna; (56 pag.)EP3511334; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 25940-35-6, Adding some certain compound to certain chemical reactions, such as: 25940-35-6, name is Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid,molecular formula is C7H5N3O2, 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 25940-35-6.

2,2-Dimethyl-6′-morpholino-spiro[1,3-dioxane-5,2′-3H-benzofuran]-5′-amine (90 mg, 0.28 mmol), pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (100 mg, 0.61 mmol), HATU (180 mg, 0.47 mmol) and N,N-diisopropylamine (0.2 ml, 1.22 mmol) was stirred in N,N-dimethylformamide (5 ml) at 25 oC for 12h. The mixture was concentrated and purified by column chromatography (eluent 40% ethyl acetate: petroleum ether) to afford N-(2,2-dimethyl-6′-morpholino-spiro[1,3- dioxane-5,2′-3H-benzofuran]-5′-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (110 mg, 84% yield).

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. 25940-35-6, Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BRYAN, Marian, C.; GOBBI, Alberto; KIEFER, James, Richard, Jr.; KOLESNIKOV, Aleksandr; OLIVERO, Alan, G.; DROBNICK, Joy; LIANG, Jun; RAJAPAKSA, Naomi; (846 pag.)WO2017/108723; (2017); 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 3764-01-0, name is 2,4,6-Trichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. name: 2,4,6-Trichloropyrimidine

i22 i23 2,4,6-Trichloropyrimidine (Manchester Organics, product number Y17832, 1 1.2 g, 61 mmol, 1.0 eq.), N,N-diisopropylethylamine (23.3 mL, 134.2 mmol, 2.2 eq.) and morpholine (1 1.7 mL, 134.2 mmol, 2.2 eq.) are charged in a flask and dissolved in ethanol (120 mL). The flask is equipped with a refluxed condenser and placed in an oil bath preheated at 100 C. The reaction mixture is stirred at this temperature for 18 hours. After this time, the reaction mixture is cooled down to room temperature and volatiles are removed under reduced pressure. The resulting mixture is dissolved in dichloromethane (100 mL) and washed twice with an aqueous solution of sodium bisulfate (2 x 80 mL). The organic layer is dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure using a rotary evaporator. Products i22 and i23 are isolated by flash chromatography on silica gel (cyclohexane / ethyl acetate 3 : 1 to 1 : 1). The product fractions are pooled and evaporated to yield i22 as a colorless powder (13.8 g, 80%) and i23 as a colorless powder (2.2 g, 13% yield). 4,4′-(6-chloropyrimidine-2,4-diyl)dimorpholine (i22): 1H NMR (400 MHz, CDC13): delta 5.85 (s, 1 H), 3.71-3.75 (m, 12 H), 3.52-3.55 (m, 4 H); MS (MALDI): m/z: 285.4 ([M+H]+).4,4′-(2-chloropyrimidine-4,6-diyl)dimorpholine (i23): 1H NMR (400 MHz, CDC13): delta 5.38 (s, 1 H), 3.73-3.76 (m, 8 H), 3.52-3.54 (m, 8 H); MS (MALDI): m/z: 285.2 ([M+H]+).

With the rapid development of chemical substances, we look forward to future research findings about 3764-01-0.

Reference:
Patent; PIQUR THERAPEUTICS AG; THE TRUSTEES OF THE UNIVERSITY OF PENNESYLVANIA; FABBRO, Doriano; HEBEISEN, Paul; HILLMANN-WUELLNER, Petra; STUETZ, Anton; SEYKORA, John, T.; BEAUFILS, Florent; (182 pag.)WO2017/198347; (2017); 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. 941685-26-3, name is 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C12H18ClN3OSi, 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: 941685-26-3

(B) (R)-tert-butyl 1-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-ylcarbamate A solution of 4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (900 mg, 3.17 mmol), (R)-tert-butyl pyrrolidin-3-ylcarbamate (709 mg, 3.80 mmol) and DIPEA (618 mg, 4.75 mmol) in EtOH (20 mL) was stirred at refluxed temperature for 3 hours. The volatiles were removed under reduced pressure and the residue was dissolved in EtOAc (100 mL), washed with brine (3*10 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give the tile compound. MS (m/z): 434 (M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 941685-26-3.

Reference:
Patent; Su, Wei-Guo; Deng, Wei; Li, Jinshui; Ji, Jianguo; US2013/210831; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 934524-10-4 ,Some common heterocyclic compound, 934524-10-4, molecular formula is C13H9Cl2N3O2S, 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.

General procedure: To a solution of 8 (1 equiv) in n-BuOH (20mL), corresponding amines (1.1 equiv) and N-ethyl-N-isopropylpropan-2-amine (1.2 equiv) were added. The mixture was stirred at 100C for 5h. The mixture was diluted with EtOAc and washed successively with water and brine. The organic layer was dried over Na2SO4, filtered, and evaporated. The resulting intermediate was purified by chromatography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,934524-10-4, its application will become more common.

Reference:
Article; Wang, Ruifeng; Chen, Yixuan; Zhao, Xiangxin; Yu, Sijia; Yang, Bowen; Wu, Tianxiao; Guo, Jing; Hao, Chenzhou; Zhao, Dongmei; Cheng, Maosheng; European Journal of Medicinal Chemistry; vol. 183; (2019);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1100318-96-4, 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. 1100318-96-4, name is 4-Iodo-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H4IN3, 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.

[00304] 206 mg (0.84 mmol) of 4-iodo-7H-pyrrolo[2,3-d]pyrimidine was dissolved in 1 ml_ DMF. 37 mg (0.92 mmol) of 60% sodium hydride was added followed by 58 mul_ (0.92 mmol) of iodomethane. The reaction was quenched by adding 10 ml_ of water, the solid filtered off, washed with 10 ml_ of water, then 10 ml_ of hexanes and dried. Yield: 142 mg of a tan powder, 90% pure.

According to the analysis of related databases, 1100318-96-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2009/9740; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 705-24-8, 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. 705-24-8, name is 4,6-Dichloro-2-(trifluoromethyl)pyrimidine, molecular formula is C5HCl2F3N2, 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.

To a suspension of 2-trifluoromethyl-pyrimidine-4, 6-diol (3.25 g) in POC13 (7.89 mL) was added Et3N (5.00 mL). The mixture was stirred at 120C for 3 hr, cooled to ambient temperature, and poured into ice water. The aqueous layer was extracted with CHC13 (three times). The combined organic layer was dried over MgS04, filtrated, and concentrated under reduced pressure to give 4, 6-dichloro-2-trifluoromethyl-pyrimidine. To the solution of the above material (1.00 g) in THF (10 mL) were added iPrzNEt (0.98 mL) and 50% aqueous Me2NH (0.48 mL). The mixture was stirred at ambient temperature for 60 hr. To the solution was added saturated aqueous NaHCO3 and the aqueous layer was extracted with CHCI3 (three times). The combined organic layer was dried over MgSO4, filtered, concentrated under reduced pressure, and purified by medium-pressure liquid chromatography (silica gel, 5% to 25% EtOAc in hexane) to give (6-chloro-2- trifluoromethyl-pyrimidin-4-yl)-dimethyl-amine (728 mg). ESI MS m/e 225 M+ ; 1H NMR (300 MHz, CDC13) 8 2.77-3. 61 (m, 6 H), 6.50 (s, 1 H).

According to the analysis of related databases, 705-24-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; Arena Pharmaceuticals, Inc; WO2005/95357; (2005); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 5751-20-2, Adding some certain compound to certain chemical reactions, such as: 5751-20-2, name is 2-(Methylthio)pyrimidin-4(3H)-one,molecular formula is C5H6N2OS, 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 5751-20-2.

Preparation of 2-(3-chlorophenylamino)pyrimidin-4(3H)-one (2); To 2-(methyl-thio)pyrimidine-4(3H)-one, 1, (4.88 g, 34.37 mmol) in diglyme (20 mL) is added 3-chloroaniline (4.3 mL, 68.74 mmol). The resulting mixture is heated to reflux and stirred for 18 hours. A solid forms upon cooling the mixture to room temperature. The solid is washed with hexanes to afford 5.0 g (66percent yield) of the desired compound. 1H NMR (DMSO-d6, 300 MHz): delta 5.91 (d, J=5.7 Hz, 2H), 7.05 (d, J=7.5 Hz, 1H), 7.11 (br s, 1H), 7.32 (t, J=7.8, 15.9 Hz, 1H), 7.45 (d, J=7.8 Hz, 1H), 7.86 (d, J=4.5 Hz, 1H), 7.94 (s, 1H).

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. 5751-20-2, 2-(Methylthio)pyrimidin-4(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Djung, Jane Far-Jine; Golebiowski, Adam; Hunter, Jack A.; Shrum, Gary P.; US2007/293494; (2007); A1;; ; Patent; DJUNG, Jane Far-Jine; Golebiowski, Adam; Hunter, Jack A.; Shrum, Gary P.; US2007/293525; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia