Day: March 18, 2022

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. 289042-10-0, name is N-(5-((Diphenylphosphoryl)methyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide, molecular formula is C28H29FN3O3PS, 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. category: pyrimidines

A mixture of DPPO (19.17 g) and THF (227 ml) were warmed briefly to 40 C. until a clear solution had formed then inerted by the sequential application of vacuum and nitrogen (5 cycles). The mixture was immersed in an acetone/CO2 bath cooling the contents to -75 C. Sodium bis(trimethylsilyl)amide (37.4 ml of 1.0 M solution in THF) was added to the reaction mixture over 10 minutes from a pressure equalising dropping funnel maintaining the temperature below -74 C and forming a red solution of the anion. THF (10 ml) was rinsed through the dropping funnel into the mixture and the mixture stirred a further 1 hour at -76 C forming a red suspension. BFA (80 ml of 13.5% w/w toluene solution) was added in portions to the suspension over 20 minutes from a pressure equalising dropping funnel maintaining the temperature below -73 C. Toluene (20 ml) was rinised through the dropping funnel into the mixture and the mixture stirred a further 15 minutes at -76 C. The chilling bath was lowered and the suspension allowed to warm to 10 C over 1.5 hours. Glacial acetic acid (3.21 g) in water (15 g) was added in one portion raising the temperature to 18 C and dissolving all solids and the mixture was stirred a further 5 minutes. The mixture was concentrated by distillation at atmospheric pressure (jacket 110 C) to a temperature of 94 C collecting a total of 274 ml distillates. The concentrated mixture was cooled to 40 C, water (40 ml) was added and the mixture stirred for 5 minutes then allowed to settle for 15 minutes. The lower aqueous phase was discarded. Sodium hydrogen carbonate (2.99 g) in water (40 ml) was added and the mixture stirred for 5 minutes then allowed to settle for 15 minutes. The lower aqueous phase was discarded. Water (30 ml) was added and the mixture stirred for 5 minutes then allowed to settle for 15 minutes. The lower aqueous phase was discarded. The organic phase was transferred to a distillation apparatus with toluene (20 ml) and concentrated by distillation at atmospheric pressure (jacket 125-130 C) to a temperature of 116 C collecting 85 ml distillates. Vacuum was applied (400-500 mbar) and a further 16.5 ml distillates collected to a temperature of 111 C. The vacuum was released and the concentrated mixture allowed to cool to 80 C. Warm MeOH (140 ml, 50 C) was added with rapid stirring and the batch allowed to self-cool to 20 C over 30 minutes during which time a solid was deposited. The suspension was further cooled to 2 C for 30 minutes then the solid was collected by filtration on a sinter and pulled as dry as possible. The solid was washed with cold MeOH (60 ml, 2C.) and again pulled as dry as possible then transferred to a vacuum oven and dried overnight (50 C, 200 mbar); giving BEM (14.01 g, 67.7%). 1H NMR (CDCl3, 270 MHz) 7.65 [m, 2H, ArH], 7.09 [m, 2H, ArH], 6.52 [dd, 1H, ArCH=CH], 5.47 [dd, 1H, ArCH=CH], 3.57, 3.50 [2 x s, 6H, NCH3, SO2CH3], 3.38 [hept., 1H, ArCHMe2], 2.45, 2.30 [2x dd, 2H, CH2CO2tBu], 1.55, 1.13 [dt, dd, 2H, acetonide CH2], 1.50, 1.40 [2x s, 6H, acetonide C(CH3)2], 1.45 [s, 9H, CO2C(CH3)3], 1.27 [dd 6H, ArCH(CH3)2]

With the rapid development of chemical substances, we look forward to future research findings about 289042-10-0.

Reference:
Patent; AstraZeneca AB, AstraZeneca AB; Shionogi & amp Co., Ltd.; US2004/49036; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 85989-61-3 ,Some common heterocyclic compound, 85989-61-3, molecular formula is C6H3Cl2N3, 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.

Example 16A; 6-({2-[(7-Chloroimidazo[1,2-c]pyrimidin-5-yl)amino]ethyl}amino)nicotinonitrile 707 mg (3.20 mmol) of 5,7-dichloroimidazo[1,2-c]pyrimidine (Example 11A) are suspended in 25 ml of 2-propanol, and 1.35 g (3.52 mmol) of 6-[(2-aminoethyl)amino]nicotinonitrile trifluoroacetate (Example 13A) and 1.03 g (7.99 mmol) of DIPEA are added. The mixture is heated at 80 C. for 16 h. After this time, water is added and the precipitate which has separated out is filtered off with suction. It is washed with a little 2-propanol/water and the resulting solid is dried under high vacuum. 523 mg (50% of theory) of the product are obtained.LCMS (method 3): Rt=1.31 min. (m/z=314 (M+H)+)1H-NMR (400 MHz, DMSO-d6): delta=8.37 (d, 1H), 8.33 (t, 1H), 7.93 (s, 1H), 7.80 (s, 1H), 7.68 (d, 1H), 7.50 (d, 1H), 6.90 (s, 1H), 6.56 (s, br, 1H), 3.62 (m, 2H), 3.31 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,85989-61-3, its application will become more common.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2010/113441; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 209959-33-1, 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. 209959-33-1, name is 2-[Bis(tert-Butoxycarbonyl)amino]-5-bromopyrimidine, molecular formula is C14H20BrN3O4, 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.

Example 15 tert-Butyl 5-bromopyrimidin-2-ylcarbamate 11 To a solution of 2-[bis(tert-butoxycarbonyl)amino]-5-bromopyrimidine 10 (216 kg crude, 460 mol, assuming quantitative yield in previous step) in anhydrous ethanol (1692 L) was slowly added a solution of sodium hydroxide (55.2 kg, 1380 mol) in water (344 L) while maintaining the temperature at 0-20 C. The mixture was stirred at that temperature until the content of 2-[bis(tert-butoxycarbonyl)-amino]-5-bromopyrimidine (10) was ?0.5% by HPLC. The reaction mixture was cooled to 0-5 C. and the pH was adjusted to 7 by addition of oxalic acid (86.0 kg, 955 mol) while maintaining the temperature below 5 C. The mixture was then distilled under vacuum to a volume of 500-600 L while controlling the temperature below 50 C. Water (800 kg) was added and the mixture was stirred for 1 h. The solid was collected by filtration and stirred with water (2*500 L). The resulting solid was collected by filtration and dried under reduced pressure at 50 C. to afford tert-butyl 5-bromopyrimidin-2-ylcarbamate 11 (107 kg, 85% yield over two steps). 1H NMR (500 MHz, CDCl3) delta 8.63 (s, 2H), 8.12 (s, 1H), 1.55 (s, 9H). LCMS (ESI) m/z [M+H-Boc] 176

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 209959-33-1, 2-[Bis(tert-Butoxycarbonyl)amino]-5-bromopyrimidine.

Reference:
Patent; Genentech, Inc.; Babu, Srinivasan; Cheng, Zhigang; Gosselin, Francis; Hidber, Pirmin; Hoffmann, Ursula; Humphries, Theresa; Reents, Reinhard; Tian, Qingping; Yajima, Herbert; US2014/100366; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 3438-61-7 ,Some common heterocyclic compound, 3438-61-7, molecular formula is C5H7N3, 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.

4-methylpyrimidin-5-amine (1.09 g, 10 mmol) was dissolved in dry THF (150 mL) under nitrogen. The solution was cooled to -78C and a solution of n-BuLi was added dropwise. The solution was kept at the same temperature for 30min and then warm to r.t., stirred for 2h. Then cooled to -78C, ethyl benzoate (1.5 g, 10 mmol) in THF (30 mL) was added, and the resulting mixture was stirred at -78C for 30min, and was warmed to r.t. for lh. The reaction mixture was quenched with drop some water, and neutralized with NaHC03. EtOAc and water were added, portioned. The organic layer was concentrated and purified by by flush column chromatography on silica gel (eluting with petroleum ether/ethyl acetate =100/1-0/1), to give the title product 6-phenyl-5H-pyrrolo[3,2-d]pyrimidine (0.8 g, 41%). MS (ESI) m/z :196.1 [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. 3438-61-7, 5-Amino-4-methylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; SKELTON, Nicholas; GRADL, Stefan; BLAKE, James F.; GRAHAM, James M.; GUNAWARDANA, Indrani W.; HENTEMANN, Martin; MARLOW, Allison L.; TANG, Tony P.; WO2013/78254; (2013); A1;,
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. 1239460-82-2, name is 5,6-Dibromothieno[2,3-d]pyrimidin-4(3H)-one. A new synthetic method of this compound is introduced below., Product Details of 1239460-82-2

Zinc dust (210 mg, 3.21 mmol) was added to a solution of 5,6- dibromothieno[2,3-T|pyrimidin-4(3H)-one (910 mg, 2.94 mmol) in glacial acetic acid (8 ml) and water (2 ml). After stirring for 4 h, a second portion of zinc dust (214 mg, 3.27 mmol) was added and the heterogeneous mixture was placed into a preheated oil bath at 600C. The heterogeneous mixture became a clear solution in 30 min. The solution was diluted with water and extracted with ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford 5-bromothieno[2,3- fiT]pyrimidin-4(3H)-one as a white solid. Method [8] retention time 2.68 min by EtaPLC (M+ 231 and 233).

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, 1239460-82-2, 5,6-Dibromothieno[2,3-d]pyrimidin-4(3H)-one.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; SHAM, Hing, L.; KONRADI, Andrei, W.; HOM, Roy, K.; PROBST, Gary, D.; BOWERS, Simeon; TRUONG, Anh; NEITZ, R., Jeffrey; SEALY, Jennifer; TOTH, Gergely; WO2010/91310; (2010); 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 87253-62-1, name is 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. Formula: C8H8N4O2

General procedure: In 25ml RB flask to a solution of Compound 9 (200 mg) in dry DMF (5ml), EDCI (250 mg, 1.25eq) and DMAP (130 mg,1eq) were added followed by addition of Sulfonamide (1eq). RM was stirred at RT for 4hrs. Solvent from the reaction mixture was evaporated. To the residue water was added and acidified with 6N HCl, solid precipitated out. Solid was filtered and dried. Crude solid was purified by flash chromatography eluating with 4-8% MeOH/DCM as solvent system to give pure product.

With the rapid development of chemical substances, we look forward to future research findings about 87253-62-1.

Reference:
Article; Patil, Vikas; Kale, Manoj; Raichurkar, Anandkumar; Bhaskar, Brahatheeswaran; Prahlad, Dwarakanath; Balganesh, Meenakshi; Nandan, Santosh; Shahul Hameed; Bioorganic and Medicinal Chemistry Letters; vol. 24; 9; (2014); p. 2222 – 2225;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 53557-69-0, 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 53557-69-0 as follows.

To a solution of 6-iodopyrimidin-4-amine (442 mg, 2 mmol) in 5 mL of DMF was added (Phen)CuCF2CF3 (1.14 g, 3 mmol, purchased from Aspira scientific). The mixture was stirred at 90 C for 2 hours. Then, the mixture was poured into water and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated under vacuum. The crude product was purified by column chromatography on silica gel to give 6-(1 , 1 ,2,2,2- pentafluoroethyl)pyrimidin-4-amine. H NMR (400Mz, DMSO-c/6) delta (ppm): 6.80 (s, 1 H), 7.50(s, 2 H), 8.47 (s, 1 H). 9F-NMR (300Mz, DMSO-c/6) delta: -79.41 (s, 3 F), -1 16.10 (s, 2 F); ESI-MS(+): 214(M+1 ), ESI-MS(-): 212(M-1 ).

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; SYNGENTA PARTICIPATIONS AG; EDMUNDS, Andrew; JEANGUENAT, Andre; JUNG, Pierre Joseph Marcel; MUEHLEBACH, Michel; (150 pag.)WO2016/71214; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1993-63-1, Adding some certain compound to certain chemical reactions, such as: 1993-63-1, name is 5-Fluoro-2-methoxypyrimidin-4-amine,molecular formula is C5H6FN3O, 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 1993-63-1.

Take 27.2kg of Intermediate 5 prepared in the previous step and mix with sulfuric acid, raise the temperature to 95-105 C, maintain the temperature for 1.5h, and then lower the temperature. Then add the mixture to water, adjust the pH to 8-9, cool, and stand still. Set, filter, and dry to obtain 23.3 kg of crude product with a yield of 95.0%. Step 6: Take 20.5 kg of the crude product prepared in the previous step and mix it with 200 kg of water, add 0.6 kg of activated carbon, stir and raise the temperature, maintain the temperature for 1 h, and filter. The resulting mother liquor is cooled and crystallized, filtered, and dried to obtain 19.7 kg of 5-fluorocytosine. The yield is 96.1%, and the purity of HPLC is 99.9% or more. According to the reaction yield of each step, the total yield of the process route provided by the present invention is 57.3%.

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. 1993-63-1, 5-Fluoro-2-methoxypyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhejiang Pioneer Technology Co., Ltd.; Gao Junlong; Gao Feifei; Li Ming; Chen Xiaoping; Wei Chenhui; (8 pag.)CN108033917; (2019); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1159818-57-1 ,Some common heterocyclic compound, 1159818-57-1, molecular formula is C4H4BrN3, 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 6-bromopyrimidin-4-amine (4.17 g, 24 mmol) in 100 mL of HI was added Nal (14.4 g, 96 mmol). The mixture was stirred at ambient temperature for 2 days. Then, the mixture was adjusted to pH=10 with NaOH solution, and the solid was separated and filtered to give 6-iodopyrimidin-4- amine. H NMR (400Mz, DMSO-c/6) delta (ppm): 6.85 (s, 1 H), 6.99(s, 2 H), 7.99 (s, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1159818-57-1, its application will become more common.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; EDMUNDS, Andrew; JEANGUENAT, Andre; JUNG, Pierre Joseph Marcel; MUEHLEBACH, Michel; (150 pag.)WO2016/71214; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1398507-08-8, name is 4-((4-Amino-6-chloropyrimidin-2-yl)amino)benzonitrile. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 4-((4-Amino-6-chloropyrimidin-2-yl)amino)benzonitrile

Example 2a: Preparation of 4-(4-amino-5-bromo-6-chloropyrimidin-2-ylamino) benzonitrile (“Compound 3a”)A suspension of 4-(4-amino-6-chloropyrimidin-2-ylamino)benzonitrile (“CAPBN”, compound la; 0.4 g; 1.628 mmol) in methanol (5 ml) was cooled to 0-5 C. Bromine (167.2 mu?; 3.26 mmol; 2 eq) was added dropwise to the suspension over 10 minutes. The resulting reaction mixture was stirred at 0-5 C for 2 hours, and then water (0.83 ml) and 10 % aqueous NaOH (1.95 ml; 4.88 mmol; 3 eq) was added dropwise. The resulting suspension was stirred lhour at 0- 5 C. A solid was separated from the suspension by filtration and washed with a MeOH / water mixture (1 : 1 ; 3 ml), and dried (4h/ 40 CI 10 mbar).Yield: 423 mg (80.1 %) of 4-(4-amino-5-bromo-6-chloropyrimidin-2-ylamino)benzonitrile. Purity (HPLC/ MS): 95.71 Area %M+ 326.4 (± 2)1H NMR (DMSO-de, delta): 10.06 (s, 1H, NH), 7.96 (d, 2H, Ph-b, Ji=8.8 Hz), 7.70 (d, 2H, Ph-c, Ji=8.8 Hz), 7.50-6.50 (br, 2H, NH2)13C NMR (DMSO-^6, delta): 161.9 (s, C2), 157.0 (s, C6), 156.7 (s, C4), 144.7 (s, Ph-a), 132.9 (d, Ph-c), 1 19.6 (s, CN), 1 18.5 (d, Ph-b), 102.6 (s, Ph-d), 89.8 (s, C5)1H NMR and 13C NMR spectra for this product are shown in figures 1-2 and 3-4, respectively.

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, 1398507-08-8, 4-((4-Amino-6-chloropyrimidin-2-yl)amino)benzonitrile.

Reference:
Patent; ASSIA CHEMICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; MAJER, Maja, Sepelj; KRIZMANIC, Irena; VRBANEC, Gordana; WO2013/59572; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia