Day: March 24, 2022

Reference of 36314-98-4 ,Some common heterocyclic compound, 36314-98-4, molecular formula is C5H4N4, 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.

40-48wt.% aqueous ammonium sulfide (8.27ml, 48.5mmol) was added to a mixture of 57 (5.3g, 44.1mmol), triethylamine (6.14ml, 44.1mmol), and pyridine (28.8ml, 353mmol) and the resulting suspension was stirred at 52C for 2h. The mixture was concentrated under reduced pressure and H2O was added to the residue. The mixture was chilled to 0C and the resulting precipitate was removed by filtration to deliver 2-aminopyrimidine-4-carbothioamide (5.5g, 35.7mmol, 80% yield) as a yellow solid. 1H NMR (400MHz, DMSO-d6) delta ppm 10.23 (br. s, 1H), 9.58 (br. s, 1H), 8.42 (d, J=4.9Hz, 1H), 7.35 (d, J=4.9Hz, 1H), 6.80 (br. s, 2H). MS (ESI, pos. ion) m/z: 155.1 (M+1).

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. 36314-98-4, 2-Amino-4-cyanopyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Reichelt, Andreas; Bailis, Julie M.; Bartberger, Michael D.; Yao, Guomin; Shu, Hong; Kaller, Matthew R.; Allen, John G.; Weidner, Margaret F.; Keegan, Kathleen S.; Dao, Jennifer H.; European Journal of Medicinal Chemistry; vol. 80; (2014); p. 364 – 382;,
Pyrimidine | C4H4N2 – PubChem,
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 209959-33-1, name is 2-[Bis(tert-Butoxycarbonyl)amino]-5-bromopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-[Bis(tert-Butoxycarbonyl)amino]-5-bromopyrimidine

Step B: A mixture of 2-[bis(tert-butoxycarbonyl)amino]-5-bromopyrimidine (3.0 g, 8.0 mmol), dimethylzinc (1.2 M×8.0 mL, 9.6 mmol) and [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (130 mg, 0.16 mmol) in 1,4-dioxane (30 mL) was stirred at 110 C. for 16 h under Argon. The mixture was cooled to room temperature, diluted with ethyl acetate and washed with saturated NH4Cl, water and brine. The organic layer was dried over NaSO4, concentrated and purified by silica gel column chromatography (0-35% EtOAc in hexanes) to give a white solid, which was dissolved in trifluoroacetic acid (5.0 mL). After 5 min, the solvent was removed and the residue was partitioned between ethyl acetate and an aqueous saturated NaHCO3 solution. The organic layer was dried over NaSO4, filtered and concentrated to give the title compound (0.7 g, 80%) as a white solid. MS m/z 110.1 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 209959-33-1.

Reference:
Patent; PTC Therapeutics, Inc.; F. Hoffmann-La Roche AG; Woll, Matthew G.; Chen, Guangming; Choi, Soongyu; Dakka, Amal; Huang, Song; Karp, Gary Mitchell; Lee, Chang-Sun; Li, Chunshi; Narasimhan, Jana; Naryshkin, Nikolai; Paushkin, Sergey; Qi, Hongyan; Turpoff, Anthony A.; Weetall, Marla L.; Welch, Ellen; Yang, Tianle; Zhang, Nanjing; Zhang, Xiaoyan; Zhao, Xin; Pinard, Emmanuel; Ratni, Hasane; (317 pag.)US9617268; (2017); B2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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