Month: March 2022

Electric Literature of 14248-01-2 ,Some common heterocyclic compound, 14248-01-2, molecular formula is C5H5BrN2O, 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.

Step 2: 5-(4-Amino-3,5-dimethylphenyl)-1-methylpyrimidin-2(1H)-one [0768] The title compound is prepared from 5-bromo-1-methylpyrimidin-2(1H)-one and 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline following a procedure analogous to that described in Step 2 of Intermediate 62. The mixture is stirred for 12 hours at 70 C. LC (method 9): tR=0.63 min; Mass spectrum (ESI+): m/z=230 [M+H]+.

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. 14248-01-2, 5-Bromo-1-methylpyrimidin-2(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Ingelheim International GmbH; ECKHARDT, Matthias; FRATTINI, Sara; HAMPRECHT, Dieter; HIMMELSBACH, Frank; LANGKOPF, Elke; LINGARD, Iain; PETERS, Stefan; WAGNER, Holger; US2013/252937; (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.675-11-6, name is 4,6-Difluoropyrimidin-2-amine, molecular formula is C4H3F2N3, molecular weight is 131.0835, as common compound, the synthetic route is as follows.category: pyrimidines

EXAMPLE 5 Preparation of 6-allyloxy-2-amino-4-fluoropyrimidine (Variant A) STR13 1.14 g (0.0382 mol) of 80% sodium hydride (emulsion in linseed oil) were added at 25 C. under a nitrogen atmosphere to 70 ml of allyl alcohol. To the clear solution obtained after stirring at 40 C. for 20 minutes were added 5.0 g (0.0382 mol) of 2-amino-4,6-difluoropyrimidine, and the mixture was then stirred at 97 C. for 1.5 hours. To work up, the excess alcohol was removed by distillation under reduced pressure, the residue was taken up in methylene chloride, and the solution was washed with water, dried over magnesium sulfate and then freed of solvent. The viscous oil obtained in this way crystallized on trituration with n-pentane. 4.6 g (71.2% of theory) of the title compound of melting point 62-66 C. were obtained after filtering off, washing with water and drying.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,675-11-6, 4,6-Difluoropyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; BASF Aktiengesellschaft; US5011927; (1991); 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. 99420-75-4, name is 5-Methylpyrimidine-2-carboxylic acid, molecular formula is C6H6N2O2, 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: 99420-75-4

To a solution of 5-methylpyrimidine-2-carboxylic acid (1 g, 7.24 mmol) in DMF (72.4 mL) was added 5-methylpyrimidine-2-carboxylic acid (1 g, 7.24mmol), and N,O- dimethylhydroxylamine hydrochloride (0.777 g, 7.96 mmol). The mixture was cooled to 0 oC and 1-propanephosphonic acid cyclic anhydride, 50 wt. % solution in EtOAc (9.21 mL, 14.48 mmol) was added dropwise. The mixture was allowed to warm to RT overnight after which LCMS indicated complete conversion to product. The mixture was diluted with water, extracted with CHCl3:IPA (3:1) and washed with brine and then NaHCO3. The mixture was dried over Na2SO4, concentrated in vacuo and purified by silica gelchromatograph (0-100% heptanes:EtOAc) to yield N-methoxy-N,5- dimethylpyrimidine-2-carboxamide (0.7 g, 3.86 mmol, 53.4 % yield). 1H NMR (500 MHz, CDCl3) delta 8.61 – 8.69 (m, 2 H) 3.61 – 3.79 (m, 3 H) 3.27 – 3.47 (m, 3 H) 2.34 – 2.45 (m, 3 H). LCMS-ESI (pos.) m/z: 182.2 (M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 99420-75-4.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Yinhong; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HEATH, Julie Anne; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; KREIMAN, Charles; (308 pag.)WO2018/93579; (2018); 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 911461-47-7, name is 4,6-Dichloropyrimidine-5-carboxamide. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 911461-47-7

To a solution of 4,6-dichloropyrimidine-5-carboxamide (24.6 g, 128 mmol) in methanol (200 mL) was added a solution of sodium methylate (15.2 g, 282 mmol) in MeOH (100 mL). The resulted mixture was stirred at rt for 4.5 hours and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc/MeOH (v/v)=25/1) to give the title compound as a pale yellow solid (18.3 g, yield: 71.1%). [0686] MS (ESI, pos. ion) mz: 184.1 [M+H]+; [0687] 1H NMR (600 MHz, CDCl3) delta (ppm): 8.47 (s, 1H), 6.30 (br. s, 1H), 5.98 (br. s, 1H), 4.07 (s, 6H).

With the rapid development of chemical substances, we look forward to future research findings about 911461-47-7.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD.; Xi, Ning; Wang, Liang; Wang, Tingjin; US2015/87658; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 38275-42-2, 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. 38275-42-2, name is 5-Chloro-2-(methylthio)pyrimidine. A new synthetic method of this compound is introduced below.

Step B: 5 -chloro-2-(methylsulfonyl)pyrimidine: A solution of 5 -chloro-2- (methylsulfanyl)pyrimidine (0.6 g, 3.9 mmol) was dissolved in MeOH (15 mL) and treated with a solution of oxone (7.2 g, 12 mmol) in H20 (50 mL). Upon completion of the reaction, the solution was filtered to remove solid and the aqueous filtrate was extracted with 3:1 CHC13 :IPA.The desired sulfone was isolated as a solid with no further purification required. LCMS: m/z193.02 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,38275-42-2, 5-Chloro-2-(methylthio)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP; TANG, Haifeng; PIO, Barbara; JIANG, Jinlong; PASTERNAK, Alexander; DONG, Shuzhi; FERGUSON, Ronald Dale, II; GUO, Zack Zhiqiang; CHOBANIAN, Harry; FRIE, Jessica; GUO, Yan; WU, Zhicai; YU, Yang; WANG, Ming; WO2015/17305; (2015); 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 1211522-68-7, name is 4,6-Dichloro-3-methyl-1H-pyrazolo[3,4-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 4,6-Dichloro-3-methyl-1H-pyrazolo[3,4-d]pyrimidine

Example 12: Synthesis of Compound XIII-10; Step 1: Synthesis of 4,6-dichloro-3-methyl-l-(tetrahydro-2H-pyran-2-yl)-lH-pyrazolo[3,4- d]pyrimidine (2); 4,6-dichloro-3-methyl-l H-pyrazolo[3,4-d]pyrimidine (1, 2 g, 9.85 mmol) was taken in ethyl acetate ( 100 mL), 3,4-Dihydropyran (2.5 g, 29.55 mmol) and p-TSA (0.1 g) were added to it. Reaction was stirred at RT for overnight. Product was detected by ESMS and NMR. Reaction was basified with Sat. NaHC03, organic layer was seperated, dried over sodium sulfate and concentrated to get 4,6- dichloro-3-methyl-l -(tetrahydro-2H-pyran-2-yl)-l H-pyrazolo[3,4-d]pyrimidine (2, 2.6 g, 92%). Crude product was used as such for the next step. NMR (400 MHz, CDC13): delta 5.95 (dd, 1 H), 4.18-4.10 (dd, 1 H), 3.83-3.76 (t, 1 H), 3.70 (s, 3H), 2.60-2.50 (m, 1H), 2.18-2.10 (m, 1H), 1.92- 1.60 (m, 4H).

With the rapid development of chemical substances, we look forward to future research findings about 1211522-68-7.

Reference:
Patent; GATEKEEPER PHARMACEUTICALS, INC.; GRAY, Nathanael, S.; ZHOU, Wenjun; WO2011/140338; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 3551-55-1 , The common heterocyclic compound, 3551-55-1, name is 2,4-Dimethoxypyrimidine, molecular formula is C6H8N2O2, 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.

2,4-Dimethoxypyrimidine (1.4 g, 10 mmol) was dissolved in tetrahydrofuran (14 mL) under nitrogen. cool down to around 0 C, 1M magnesium dichloride(2,2,6,6-tetramethylpiperidine)lithium salt (11 mL, 11 mmol) was added dropwise with stirring. Stirring was continued for 2 hours, then iodine (2.79 g, 11 mmol) was added with stirring. After maintaining the low temperature reaction for 2 hours, it was naturally warmed to room temperature and stirring was continued for 6 hours. The reaction was quenched with aqueous ammonium chloride solution was poured into ethyl acetate and extracted three times were combined, washed, dried, and concentrated. After the obtained crude column chromatography, 5-iodo-2,4-dimethoxypyrimidine (2.34 g, yield: 88%) was obtained

The synthetic route of 3551-55-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fuxin Fulongbao Pharmaceutical Technology Co., Ltd.; Cai Fanping; Li Xinming; (5 pag.)CN109232385; (2019); A;,
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. 29509-91-9, name is 4-Chloro-2,6-diphenylpyrimidine. A new synthetic method of this compound is introduced below., Product Details of 29509-91-9

4-Chloro-2.6-diphenylpyrimidine (10.00g, 37.49mmol), 4′-bromo-4-biphenylboronic acid (10.34g, 37.35mmol), tetrakis (triphenylphosphine) palladium (2.15g, 1.87 mmol), potassium carbonate (10.32g, 74.70mmol), tetrabutylammonium chloride (0.43g, 1.86mmol), toluene (80mL), ethanol (40mL) and deionized water (20mL) were added to a round bottom flask, and nitrogen The temperature was increased to 78 C under protection and stirred for 10 hours. The reaction solution was cooled to room temperature, and toluene (300 mL) was added for extraction. The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The alkane was purified by silica gel column chromatography as a mobile phase, and then recrystallized from a dichloromethane / ethyl acetate system to obtain a white solid intermediate IF-1 (12.18 g, yield 84%).

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, 29509-91-9, 4-Chloro-2,6-diphenylpyrimidine.

Reference:
Patent; Shanxi Laite Optoelectric Materials Co., Ltd.; Ma Tiantian; Yang Min; Nan Peng; (69 pag.)CN110615759; (2019); A;,
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 1192813-64-1, name is 2-Chloro-5-(difluoromethoxy)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 1192813-64-1

16. Reaction of 2-chloro-5-(difluoromethoxy)pyrimidine with zinc cyanide, tris(dibenzylideneacetone)dipalladium(0), 1 , 1 ‘-bis(diphenylphosphino)ferrocene, and zinc dust in Lambda/,/V-dimethylacetamide at elevated temperature provided 5- (difluoromethoxy)pyrimidine-2-carbonitrile. This material was hydrolyzed with aqueous sodium hydroxide solution to afford the requisite 5-(difluoromethoxy)pyrimidine-2- carboxylic acid.

With the rapid development of chemical substances, we look forward to future research findings about 1192813-64-1.

Reference:
Patent; PFIZER INC.; BRODNEY, Michael Aaron; BECK, Elizabeth Mary; BUTLER, Christopher Ryan; ZHANG, Lei; O’NEILL, Brian Thomas; BARREIRO, Gabriela; LACHAPELLE, Erik Alphie; ROGERS, Bruce Nelsen; WO2015/155626; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 14248-01-2 ,Some common heterocyclic compound, 14248-01-2, molecular formula is C5H5BrN2O, 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 5-bromo-1-methylpyrimidin-2(1H)-one (S2, 1 equiv) in DMF/H2O (9:1, 10 vol) was added compound S1 (1 equiv), K2CO3(2 equiv), and tetrakis(triphenylphosphine)palladium (0.1 equiv). The reaction mixture was stirred at 90 C. for 5 h and then concentrated under reduced pressure. The remaining residue was purified by column chromatography on silica gel to give compound S3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14248-01-2, its application will become more common.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAK, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (905 pag.)WO2017/35353; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia