Day: June 22, 2021

Adding a certain compound to certain chemical reactions, such as: 14394-70-8, 2-Chloro-5-methylpyrimidin-4-amine, 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, Formula: C5H6ClN3, blongs to pyrimidines compound. Formula: C5H6ClN3

[0126] 2-chloro-5-methyl-pyrimidin-4-ylamine (0.408 g, 2.83 mmol, 1 equiv), 4-Bromo- 1,2-dichloro-benzene (0.704 g, 3.12 mmol, 1.1 equiv), cesium carbonate (2.8 g, 8.49 mmol, 3 equiv), 4,5-bis(diphenylphosrhohino)-9,9-dimethyl xanthene (0.328 g5 0.57 mmol, 0.2 equiv) and tris(dibenzylideneacetone) dipalladium (0.26 g, 0.283 mmol, 0.1 equiv) were combined in 30ml microwave vessel. Reactants were then diluted with 12ml dioxane and microwaved for 25 minutes at 160 0C. Reaction vessel was then spun down, decanted and evaporated to dryness. Resulting solids were diluted with DCM and adsorbed onto silica gel. Chromatography (gradient of 15% ethyl acetate in hexanes up to 80% ethyl acetate in hexanes) afforded the title intermediate 19 as a pale yellow powder (0.366 g, 45% yield). MS (ESI+): 287.97 (M+H), r.t. = 3.12 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14394-70-8, 2-Chloro-5-methylpyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; TARGEGEN, INC.; WO2007/53452; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1195768-23-0 , The common heterocyclic compound, 1195768-23-0, name is N-(3-(2-(tert-Butyl)-5-(2-chloropyrimidin-4-yl)thiazol-4-yl)-2-fluorophenyl)-2,6-difluorobenzenesulfonamide, molecular formula is C23H18ClF3N4O2S2, 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 D: A/-{3-[5-(2-amino-4-pyhmidinyl)-2-(1 ,1 -dimethylethyl)-1 ,3-thiazol-4-yl]-2- fluorophenyl}-2,6-difluorobenzenesulfonannideIn 1 gal pressure reactor, a mixture of A/-{3-[5-(2-chloro-4-pyrinnidinyl)-2-(1 ,1 – dimethylethyl)-1 ,3-thiazol-4-yl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide (120 g) prepared in accordance with Step C, above, and ammonium hydroxide (28-30%, 2.4 L, 20 vol) was heated in the sealed pressure reactor to 98-103 C and stirred at this temperature for 2 hours. The reaction was cooled slowly to room temperature (20 C) and stirred overnight. The solids were filtered and washed with minimum amount of the mother liquor and dried under vacuum. The solids were added to a mixture of EtOAc (15 vol)/ water (2 vol) and heated to complete dissolution at 60-70 C and the aqueous layer was removed and discarded. The EtOAC layer was charged with water (1 vol) and neutralized with aq. HCI to ~pH 5.4-5.5. and added water (1 vol). The aqueous layer was removed and discarded at 60-70 C. The organic layer was washed with water (1 vol) at 60-70 C and the aqueous layer was removed and discarded. The organic layer was filtered at 60 C and concentrated to 3 volumes. EtOAc (6 vol) was charged into the mixture and heated and stirred at 72 C for 10 min , then cooled to 20C and stirred overnight. EtOAc was removed via vacuum distillation to concentrate the reaction mixture to ~3 volumes. The reaction mixture was maintained at ~65-70C for ~30mins. Product crystals having the same crystal form as those prepared in Example 58b (and preparable by the procedure of Example 58b), above, in heptanes slurry were charged. Heptane (9 vol) was slowly added at 65-70 C. The slurry was stirred at 65-70 C for 2- 3 hours and then cooled slowly to 0-5C. The product was filtered, washed withEtOAc/heptane (3/1 v/v, 4 vol) and dried at 45C under vacuum to obtain A/-{3-[5-(2- amino-4-pyrimidinyl)-2-(1 ,1 -dimethylethyl)-1 ,3-thiazol-4-yl]-2-fluorophenyl}-2,6- difluorobenzenesulfonamide (102.3 g, 88%).

The synthetic route of 1195768-23-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; DUMBLE, Melissa; KUMAR, Rakesh; LAQUERRE, Sylvie; LEBOWITZ, Peter; WO2011/47238; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 934524-10-4, Adding some certain compound to certain chemical reactions, such as: 934524-10-4, name is 2,4-Dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine,molecular formula is C13H9Cl2N3O2S, 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 934524-10-4.

To a stirred solution of 4-methoxyphenol (87 mg, 0.70 mmol) in DMF (10 mL) was added Cs2CO3 (229 mg, 0.70 mmol). After 10 min, 2,4-dichloro-N-tosylpyrrolopyrimidine 3 (200 mg, 0.58 mmol) was added and the mixture was stirred at room temperature for 30 min. The reaction mixture was diluted with H2O (40 mL) and extracted with EtOAc (2 * 30 mL). The combined organic extracts were washed with brine (6 * 25 mL), dried, filtered and the solvent was removed in vacuo to give a grey residue. The residue was purified by flash chromatography (20% EtOAc/Hexanes) and recrystallised from n-PrOH to give 5c (150 mg, 51%) as a white solid; mp 161-164 C; deltaH (CDCl3): 8.10 (2H, d, J 8.0 Hz), 7.55 (1H, d, J 4.0 Hz), 7.32 (2H, d, J 8.0 Hz), 7.06 (2H, d, J 9.0 Hz), 6.90 (2H, d, J 9.0 Hz), 6.41 (1H, d, J 4.0 Hz), 3.81 (3H, s), 2.40 (3H, s); deltaC (CDCl3): 163.0, 157.5, 154.1, 153.2, 146.2, 145.5, 134.3, 129.9, 128.7, 124.9, 122.2, 114.7, 106.6, 102.3, 55.6, 21.7; m/z (ESI): 430.0 (M[35Cl]H+), 432.0 (M[37Cl]H+); HRMS (ESI): M[35Cl]H+, found 430.0636. C20H17ClN3O4S+ requires 430.0623.

According to the analysis of related databases, 934524-10-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; O’Brien, Nathan J.; Brzozowski, Martin; Buskes, Melissa J.; Deady, Leslie W.; Abbott, Belinda M.; Bioorganic and Medicinal Chemistry; vol. 22; 15; (2014); p. 3879 – 3886;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 18740-38-0, 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.18740-38-0, name is Thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione, molecular formula is C6H4N2O2S, molecular weight is 168.1732, as common compound, the synthetic route is as follows.

To a solution of 1H-thieno[2,3-d]pyrimidine-2,4-dione (62) (92.8 mg, 0.552 mmol) in toluene (1 mL) were added N,N-dimethylaniline (0.140 mL, 1.10 mmol) and phosphoryl chloride (0.280 mL, 3.00 mmol). The reaction mixture was warmed to 100 C and stirred for 3 h. After cooling to room temperature, H2O was added to the reaction mixture and the mixture was extracted with CHCl3. The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo to give 2,4-dichlorothieno[2,3-d]pyrimidine (63). This compound was used for the next reaction without further purification.To a solution of 63 in DMF (4 mL) was added ethyl 2-(4-aminophenyl)acetate (95.2 mg, 0.531 mmol) and the reaction mixture was stirred at 65 C for 2.5 h. After cooling, H2O was added to the reaction mixture and the mixture was extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was chromatographed (EtOAc/hexane = 0% to 100%) to give the title compound (85.9 mg, 0.247 mmol, 45%) as a colorless solid. 1H NMR (CDCl 3) delta: 1.28 (3H, t, J = 7.4 Hz), 3.64 (2H, s), 4.18 (2H, q, J = 7.4 Hz), 7.03 (1H, d, J = 5.7 Hz), 7.21 (1H, s), 7.29 (1H, d, J = 5.7 Hz), 7.32 (2H, d, J = 8.6 Hz), 7.56 (2H, d, J = 8.6 Hz).

Statistics shows that 18740-38-0 is playing an increasingly important role. we look forward to future research findings about Thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione.

Reference:
Article; Goto, Taiji; Shiina, Akiko; Yoshino, Toshiharu; Mizukami, Kiyoshi; Hirahara, Kazuki; Suzuki, Osamu; Sogawa, Yoshitaka; Takahashi, Tomoko; Mikkaichi, Tsuyoshi; Nakao, Naoki; Takahashi, Mizuki; Hasegawa, Masashi; Sasaki, Shigeki; Bioorganic and Medicinal Chemistry Letters; vol. 23; 11; (2013); p. 3325 – 3328;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 18592-13-7, 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. 18592-13-7, name is 6-(Chloromethyl)pyrimidine-2,4(1H,3H)-dione. A new synthetic method of this compound is introduced below.

6-[(4-Fluorophenyl)sulfanylmethyl]-1H-pyrimidine-2,4-dione DBU (4.02 mL, 26.91 mmol) was added to 4-fluorobenzenethiol (3.45 g, 26.91 mmol), in DMF (90 mL) at RT. The resulting solution was stirred at 20 C. for 15 minutes. 6-(Chloromethyl)-1H-pyrimidine-2,4-dione (2.88 g, 17.94 mmol) was then added and the reaction stirred for 4 hours. The reaction mixture was concentrated and diluted with DCM (100 mL), and washed with water (100 mL). The aqueous layer was acidified with 2M hydrochloric acid to give a white solid which was filtered and washed with water then dried under vacuum to give desired product (2.5 g). NMR Spectrum: 1H NMR (400.132 MHz, DMSO-d6) delta 3.80 (2H, s), 5.20 (1H, s), 7.18-7.23 (2H, m), 7.45-7.49 (2H, m), 10.90 (1H, s), 10.93 (1H, s)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,18592-13-7, its application will become more common.

Reference:
Patent; AstraZeneca AB; US2009/18134; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 32779-36-5, 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. 32779-36-5, name is 5-Bromo-2-chloropyrimidine, molecular formula is C4H2BrClN2, 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 solution of 5-bromo-2-chloropyrimidine (3 g, 15.50 mmol) in acetonitrile (40 mL) was added morpholine (4.1 mL, 47 mmol) and potassium carbonate (11 g, 78.80 mmol) . The mixture was heated at 85 and stirred for 10 h. The reaction mixture was cooled to rt and concentrated in vacuo. The residue was diluted with water (30 mL) . The resulting mixture was extracted with DCM (40 mL × 3) . The combined organic layers were dried over anhydrous Na2SO4and concentrated in vacuo to give a white solid product (3.6 g, 95) .[1814]MS (ESI, pos. ion) m/z: 245.9 [M+1]+.

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 32779-36-5, 5-Bromo-2-chloropyrimidine.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Bing; ZHANG, Yingjun; CHENG, Changchung; HUANG, Jiuzhong; BAI, Shun; REN, Xingye; LI, Zhi; ZHOU, Youbai; (368 pag.)WO2016/615; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 32779-37-6, 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 32779-37-6, name is 2,5-Dibromopyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

j0120] To a solution of2-(4-fluorophenyl)ethanol (0.566 g) in TRF (10 mE) was added NaR (0.269 g). The mixture was stirred at room temperature for 2 hours, before 2,5-dibro- mopyrimidine (0.8 g) was added. The mixture was stirred at room temperature for 16 h. The reaction was quenched with water and extracted with EtOAc (2×20 mE). The organic layers were combined, dried over MgSO4 and concentrated under vacuum. The residue was purified by silica gel column (Rex/EtOAc=1 00:5) to give 5-bromo-2-(4-fluoropheneth- oxyl)pyrimidine (0.7 g). ECMS (M+R)=297.0.

According to the analysis of related databases, 32779-37-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; Naidu, B. Narasimhulu; Patel, Manoj; Romine, Jeffrey Lee; St. Laurent, Denis R.; Wang, Tao; Zhang, Zhongxing; Kadow, John F.; US2015/232463; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 211244-81-4, 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.211244-81-4, name is 2-(Methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one, molecular formula is C8H7N3OS, molecular weight is 193.23, as common compound, the synthetic route is as follows.

2-methylthio-pyrido [2,3-d] pyrimidin-7-one (300mg) (as shown in the formula the compound 4-b) dispersingIn glacial acetic acid (10ml), was added bromine (0.16mL), the reaction mixture was stirred at room temperature 48h. After completion of the reactionDichloromethane was added, filtered, washed with methanol to give a white solid (390mg, 92%) (as defined in formulaThe compound represented by 4-c):

The chemical industry reduces the impact on the environment during synthesis 211244-81-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shanghai Pharmaceutical Group Inc.; Wan, Huixin; Xu, Zhiyong; Shi, Chen; Li, Chunli; Xu, Zhenmin; Xia, Guangxin; Ma, Ke; Li, Yufeng; (59 pag.)CN105481858; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 312613-82-4, 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. 312613-82-4, name is Pyrimidine-2-carboximidamide acetate, molecular formula is C7H10N4O2, 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.

In a dry, IL round bottom flask 845 ml of methanol was taken. To this 16 g sodium metal was added at room temperature till it was dissolved, under cooling to obtain sodium methoxide. 98.23 g of diethyl-2-(2-methoxy phenoxy) malonate (0.34 mole) was added into it and stirred at room temperature for 30 min to 1 hrs and subsequently added 65 g pyrimidine-2-carboxamidine (0.23 moles) in one lot. Further the reaction mixture was stirred at room temperature for 15-30 min, then refluxed the reaction mixture for 4-5 hrs. The reaction mixture was cooled, dumped into cold water and adjusted to pH-2 using hydrochloric acid. The solid obtained was filtered off, washed with water till neutral, suck dried to obtain 4,6- dihydroxy-5-(2-methoxy phenoxy)[2, 2′]bipyrimidine

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 312613-82-4, Pyrimidine-2-carboximidamide acetate.

Reference:
Patent; CADILA HEALTHCARE LIMITED; SATA, Kaushilk; PANDEY, Bipin; WO2010/32261; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 171408-73-4, 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. 171408-73-4, name is 2,5-Dibromo-4-methylpyrimidine, molecular formula is C5H4Br2N2, 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.

Sodium hydride (0.128g, 60% disp. in oil) was added to a stirred solution of 2-methyl- 1,2, 5-thiadiazolidine 1, 1-dioxide (0.433g) in THF (10ml). DMF (10ml) was added and the mixture heated at 80C for 5min then a solution of the product from step (i) (0.8g) in DMF (SML) was added. The mixture was heated at 60C for 10MIN, poured into water (100ml), acidified with citric acid and extracted with ethylacetate. The organics were evaporated under reduced pressure and the residue purified by chromatography on silica eluting with diethylether, yield 0.58g. 1H NMR CDC13 : 8 8.50 (s, 1H), 4.05 (t, 2H), 3.45 (t, 2H), 2.87 (s, 3H), 2.58 (s, 3H). MS: APCI (+ve) 307/9

According to the analysis of related databases, 171408-73-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; WO2004/89885; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia