Pyrimidines

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;,
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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);,
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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;,
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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;,
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Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 105806-13-1, name is 4,6-Dichloro-5-fluoro-2-methylpyrimidine, the common compound, a new synthetic route is introduced below. name: 4,6-Dichloro-5-fluoro-2-methylpyrimidine

Part A: 4-Chloro-6-[(2S)-2,4-dimethyl-1-piperazinyl]-5-fluoro-2-methylpyrimidine. To 4,6-dichloro-5-fluoro-2-methylpyiotamidine (0.309 g, 1.71 mmol) and triethylamine (0.83 ml_, 5.98 mmol) in THF (6.0 ml.) was added (3S)-1 ,3-dimethylpiperazine dihydrochloride (Example 64) (0.320 g, 1.71 mmol). MeOH (3 ml.) was added to improve solubility and the reaction was stirred for 4 days at room temperature. The solvent was removed in vacuo, and ether, THF and water were added to the resulting residue. The organics were dried (Na2SO4) and concentrated in vacuo to provide 4-chloro-6-[(2S)-2,4-dimethyl- 1-piperazinyl]-5-fluoro-2-methylpyrimidine as an orange solid (0.277 g, 63%). LCMS: (M+H)+ = 259.3.

The synthetic route of 105806-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/61879; (2009); A1;,
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Pyrimidine – Wikipedia

Reference of 1439-09-4, 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.1439-09-4, name is 5-Bromo-4-methylpyrimidine, molecular formula is C5H5BrN2, molecular weight is 173.01, as common compound, the synthetic route is as follows.

Preparation 4A: 4-Methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyrimidine[00135] Nitrogen was bubbled into a mixture of 5-bromo-4-methylpyrimidine (0.100 g, 0.578 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (0.191 g, 0.751 mmol), and potassium acetate (0.129 g, 1.316 mmol) in DMSO (2.89 mL) for 10 min. Then 1 , 1 ‘-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.019 g, 0.024 mmol) was added and the reaction mixture was heated at 90 C overnight. The reaction was quenched with FLO. The reaction mixture was extracted with EtOAc (3X). The organic phases were combined, dried over Na2S04, filtered, and concentrated to afford the title compound (127 mg, 100%) as a dark brown residue.

Statistics shows that 1439-09-4 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-4-methylpyrimidine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; HUANG, Audris; VELAPARTHI, Upender; LIU, Peiying; WO2013/49263; (2013); 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.14080-59-2, name is 4-Chlorothieno[2,3-d]pyrimidine, molecular formula is C6H3ClN2S, molecular weight is 170.62, as common compound, the synthetic route is as follows.Recommanded Product: 4-Chlorothieno[2,3-d]pyrimidine

General procedure: alpha,beta-unsaturated tosylhydrazones 1 (0.11 mmol, 1.1 equiv), heteroaryl chlorides 2 (0.1 mmol, 1 equiv), Cs2CO3 (0.25 mmol, 2.5 equiv) and MeCN (1 mL) were added to a tube. The mixture was stirred at 60 C until the heteroaryl chlorides was completely disappeared for 4-8h. After cooling to room temperature, the mixture was quenched with NH4Cl (2 mL, saturated aqueous solution) and extracted with CH2Cl2 (3 × 2 mL). The combined organic phases were dried over Na2SO4 and solvents removed in vacuo. The residue was purified by flash column chromatography on silica gel with ethyl acetate/petroleum ether (1:10-1:4, V/V) as the eluent, affording the desired product 3 and 4.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14080-59-2, 4-Chlorothieno[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Zeng, Lin; Guo, Xiao-Qiang; Yang, Zai-Jun; Gan, Ya; Chen, Lian-Mei; Kang, Tai-Ran; Tetrahedron Letters; vol. 60; 33; (2019);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 91717-22-5, name is 2-Amino-4-piperidino-6-methylpyrimidine, the common compound, a new synthetic route is introduced below. Recommanded Product: 91717-22-5

General procedure: Briefly, 4-methyl-6-(piperidin-1-yl)pyrimidin-2-amine 1 (0.30 mmol), benzaldehyde 2a (0.30 mmol), 10 equiv of dimethyl malonate 3a (3 mmol), and chiral catalyst Q4(10 mol%) were added to capped vials at 60C and stirred for 36 h. After completion of the reaction, as observed by TLC, the mixture was directly purified by column chromatography on silica gel (EtOAc/hexane=8:1), affording the product (R)-4a. However, the product (S)-4a was obtained using the Q5 catalyst. Enantiomeric excess of the product was determined by HPLC analysis using a Chiralpak IA column.

The synthetic route of 91717-22-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bai, Song; Liu, Shan; Zhu, Yunying; Zhao, Kunhong; Wu, Qin; Synlett; vol. 29; 14; (2018); p. 1921 – 1925;,
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Pyrimidine – Wikipedia

Related Products of 111196-81-7, 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 111196-81-7 as follows.

Step D: Preparation of 4-(l-(5-Ethylpyrimidin-2-yl)piperidin-4-yloxy)-5-fluoro-6- (2-methyl-6-(methylsulfonyl)pyridin-3-yloxy)pyrimidine.To a solution of 5-fluoro-4-(2-methyl-6-(methylsulfonyl)pyridin-3-yloxy)-6-(piperidin- 4-yloxy)pyrimidine hydrochloride (50.0 mg, 0.119 mmol) and 2-chloro-5-ethylpyrimidine (17.0 mg, 0.119 mmol) in IPA (2 mL) was added triethylamine (0.166 mL, 1.194 mmol). The reaction mixture was heated at 100 C under microwave irradiation for 3 h and then concentrated under reduced pressure. The residue was taken up in EtOAc and washed with water. The EtOAc layer was dried over anhydrous Na2S04, filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography to give the title compound as a white solid (21.0 mg, 36%). Exact mass calculated for C22H25FN6O4S: 488.2, found: LCMS m/z = 489.4 [M+H]+; lU NMR (400 MHz, CDC13) delta ppm 1.14 (t, = 8.0 Hz, 3H), 1.69-1.77 (m, 2H), 2.06-2.11 (m, 2H), 2.45 (q, = 8.0 Hz, 2H), 2.47 (s, 3H), 3.31 (s, 3H), 3.49-3.55 (m, 2H), 4.20-4.26 (m, 2H), 5.43-5.47 (m, 1H), 8.01 (d, = 8.0 Hz, 1H), 8.04 (d, = 8.0 Hz, 1H), 8.25 (s, 1H), 8.27 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,111196-81-7, its application will become more common.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; WO2012/145604; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia