Pyrimidines

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. 104048-92-2, name is 4-(Trifluoromethyl)pyrimidin-2(1H)-one, the common compound, a new synthetic route is introduced below. Recommanded Product: 104048-92-2

Example 250 Methyl-phenyl-carbamic Acid 4-trifluoromethyl-pyrimidin-2-yl Ester A solution of 4-(trifluoromethyl)-2-pyrimidol (0.49 g, 3.00 mmol), 1-methyl-3-(methyl-phenyl-carbamoyl)-3H-imidazol-1-ium iodide (1.03 g, 3.00 mmol) and triethylamine (0.42 ml, 3.00 mmol) in acetonitrile (15 ml) was stirred at room temperature for 3 days. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane (30:70)) yielding the title compound (0.35 g, 39% yield) as a colourless oil. 1H NMR (300 MHz, CDCl3): delta 3.45 (br.s, 3H), 7.28 (m, 1H), 7.38 (m, 4H), 7.52 (br.s, 1H), 8.93 (br.s, 1H); HPLC-MS (Method A): m/z=320 (M+Na); Rt=3.58 min.

The synthetic route of 104048-92-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ebdrup, Soren; de Jong, Johannes Cornelis; Jacobsen, Poul; Hansen, Holger Claus; Vedso, Per; US2003/166644; (2003); A1;,
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Synthetic Route of 5750-76-5 ,Some common heterocyclic compound, 5750-76-5, molecular formula is C4HCl3N2, 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 2-(isopropylsulfonyl)aniline (3.0 g,15.1 mmol) in DMF (80 mL) was added sodium hydride (1.2 g,30.1 mmol, 60% in mineral oil) at 0 C. After stirring for 30 min,2,4,5-trichloropyrimidine was added to the reaction mixture followedby warming the mixture to room temperature. After stirringfor 2 h, the reaction mixture was quenched with ice and dilutedwith excess water. The precipitate was filtered and the solid wasdried by blowing nitrogen gas to obtain 3c as an off-white solid(3.75 g, 72%). 1H NMR (500 MHz, DMSO-d6) delta 9.81 (s, 1H), 8.56 (s,1H), 8.33-8.31 (m, 1H), 7.89 (dd, J = 7.9, 1.5 Hz, 1H), 7.88-7.84 (m,1H), 7.48 (td, J = 7.6, 1.2 Hz, 1H), 3.58-3.48 (m, 1H), 1.16 (d, J = 6.7,6H); LC/MS (ESI) m/z 346.18 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5750-76-5, its application will become more common.

Reference:
Article; Jang, Jaebong; Son, Jung Beom; To, Ciric; Bahcall, Magda; Kim, So Young; Kang, Seock Yong; Mushajiang, Mierzhati; Lee, Younho; Jaenne, Pasi A.; Choi, Hwan Geun; Gray, Nathanael S.; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 497 – 510;,
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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.1421372-94-2, name is N-(4-Fluoro-2-methoxy-5-nitrophenyl)-4-(1-methyl-1H-indol-3-yl)pyrimidin-2-amine, molecular formula is C20H16FN5O3, molecular weight is 393.3712, as common compound, the synthetic route is as follows.Formula: C20H16FN5O3

3. Synthesis of intermediate 053-5 The intermediate 053-4 (1.2 g, 4.95 mmol) as a raw material was dissolved in 20 mL ofNMP at room temperature in a 50 mL of single-necked flask, followed by adding the intermediate 006-5 (19.5 g, 49.6 mmol) and anhydrous potassium carbonate (2.06 g , 14.9 mmol) into the reaction system. The reaction was heated to 100C and then carried out for 2 h. After the reaction was completed, the reaction was quenched by adding 100 mL of ice water to the mixture. A solid was precipitated, collected, dissolved in 200 mL of methylene chloride and washed once with 100 mL of saturated sodium chloride solution. The organic phases were dried over sodium sulfate and spin-dried to give 1.2 g of the intermediate 053-5 (47%) as a brown solid. LCMS: 518.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1421372-94-2, N-(4-Fluoro-2-methoxy-5-nitrophenyl)-4-(1-methyl-1H-indol-3-yl)pyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai Shaletech Technology Co., Ltd.; JIANG, Yueheng; (143 pag.)EP3216786; (2017); A1;,
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Application of 7752-78-5, 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.7752-78-5, name is 5-Bromo-2-methylpyrimidine, molecular formula is C5H5BrN2, molecular weight is 173.01, as common compound, the synthetic route is as follows.

To a solution of 5- bromo-2 -methyl-pyrimidine (700 mg, 4.05 mmol) and tetrahydropyran-4-amine (818 mg, 8.09 mmol) in toluene (12 ml) was added BINAP (504 mg, 0.81 mmol), Pd(OAc)2 (91 mg, 0.40 mmol) and Cs2C03 (2.64 g, 8.09 mmol). The mixture was stirred under N2 at 100 °C for 3 h. (1528) The mixture was poured into ethyl acetate (100 ml) and washed with 10: 1 H20 / methanol (4 x 100 ml). The EtOAc phase was concentrated in vacuo. The residue was purified by FCC (33 – 100 percent EtOAc in petroleum ether) to give the title compound as a white solid (Y = 45 percent). H NMR (400 MHz, chloroform-J) d ppm 8.07 (s, 2H), 4.05 – 3.95 (m, 2H), 3.57 – 3.48 (m, 3H), 2.61 (s, 3H), 2.06 – 2.00 (m, 2H), 1.55 – 1.44 (m, 2H).

The chemical industry reduces the impact on the environment during synthesis 7752-78-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NODTHERA LIMITED; HARRISON, David; WATT, Alan Paul; BOCK, Mark G.; (334 pag.)WO2019/121691; (2019); A1;,
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Related Products of 1074-40-4, 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 1074-40-4, name is 4,6-Dichloro-2-methoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

E&urphile I;I- 16-[2-(2.4-DkhIoiO-rhohgHVJ >-ethvS3iJiino|-2-me.hyi-pymidir;-4-yl j-rhoyrrhthetaine-3-alphaifboxyJsc ^cidSic|> . : lambda .soh?ion of 4,6-dich]uro-2-rskappalhoxypyrirHfdine (0,7 g_J, 2-f2,4-dichloro-phelambdayi’}-e.hykitauni?e (0,74 g) and Na>COj (0.88 gs hi EfOH (25 mU is heated at 80″C for 3 hours and poured nio wafer (400 nttj. The resulting solid is filtered and air dried to afford (6Patent; SANOFI-AVENTIS; WO2007/121280; (2007); A1;,
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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. 2380-63-4, name is 1H-Pyrazolo[3,4-d]pyrimidin-4-amine, the common compound, a new synthetic route is introduced below. Recommanded Product: 2380-63-4

1H-[3,4-d]pyrazolopyrimidin-4-amine(5.3g, 39mmol) andN-Iodosuccinimide (13.3 g, 59 mmol) was suspended in N,N-dimethylformamide,The reaction was heated to 80C under a nitrogen atmosphere for 12 hours.After the reaction is completed, it is cooled to room temperature, water is added, and a large amount of solids are precipitated and filtered with a Buchner funnel.Solids in turn with saturated sodium thiosulfate solution,Water and hot ethanol are washed twice each.The oil pump was drained to give 7.8 g of the target compound in a yield of 77%.

The synthetic route of 2380-63-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhao Yujun; Chen Deheng; Yan Ziqin; Guo Dexiang; (85 pag.)CN107759602; (2018); A;,
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Reference of 939986-65-9 , The common heterocyclic compound, 939986-65-9, name is 6-Chloropyrimidine-4-carbonitrile, molecular formula is C5H2ClN3, 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.

The title compound (1-60) was prepared using the procedure for Example 17, using 4- hydroxy- 1H-indazole in Step 1. The free base form of the title compound was purified via silica gel (eluting with 1-20% MeOH in DCM) and then converted to the hydrochloride salt, using 2 M HC1 in ether. ?H NIVIR (300 IVIHz, DMSO-d6): 8.78 (s, 1H), 8.60 (br s, 3H), 7.77 (s, 1H), 7.48 (m, 1H), 7.35-7.45 (m, 2H), 6.94(m, 1H), 4.10-4.20(m, 2H).; A mixture of 6-hydroxyindole 1 (157 mg, 1.18 mmol), 6-chloropyrimidine-4-carbonitrile (150 mg, 1.07 mmol), K2C03 (444 mg, 3.21 mmol), DMF (2 mL), and THF (4 mL), was stirred at RT for 20 h. Additional 6-chloropyrimidine-4-carbonitrile (30 mg, 0.2 15 mmol) was added and the mixture stirred at RT for a further 16 h. The mixture was concentrated under reduced pressure. The residue was purified (silica gel; eluting 0 to 100% EtOAc in hexanes), to afford compound 2 (190 mg, 56%) as a yellow solid. LCMS Mass: 237.0 (M+1).To a stirred solution of compound 2 (40 mg, 0.169 mmol) in EtOAc (3 mL) and HOAc (0.3 mL) at RT, was added 10% Pd/C (10 mol%). The reaction mixture was stirred at RT under hydrogen (1 atmosphere pressure) for 1 h. The reaction mixture was filtered through a pad of celite, and the filtrate was concentrated under reduced pressure. The residue was purified via preparative HPLC (Waters XTerra Prep MS C-18 OBD 5 jiM 50 x 100mm column; eluting with 10-90% ACN/H20 containing 0.1% TFA, over 20 mm), followed by silica gel (eluting 0 to 100% EtOAc in hexanes), to afford compound 1-17 (3 mg, 7%) as a solid. ?H NIVIR (300 IVIFIz, MeOH-d4): 8.76 (m, 1H), 7.61 (m, 1H), 7.29 (m, 1H), 7.18 (m, 1H), 6.94 (m, 1H), 6.80 (m, 1H), 6.49 (m, 1H), 4.22 (s, 2H); LCMS Mass: 241.0 (M+1).

The synthetic route of 939986-65-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMAKEA, INC.; ROWBOTTOM, Martin, W.; HUTCHINSON, John, Howard; (185 pag.)WO2017/3862; (2017); A1;,
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Electric Literature of 13479-88-4 , The common heterocyclic compound, 13479-88-4, name is 5,7-Dichlorothiazolo[5,4-d]pyrimidine, molecular formula is C5HCl2N3S, 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.

[00492] (+/-)-trans-Methyl 3-aminobicyclo[2.2.2]octane-2-carboxylate (284 mg, 1.55 mmol)and 5,7-dichlorothiazolo[5,4-d]pyrimidine (352 mg, 1.71 mmol) were dissolved in DMF (5 mL), then potassium carbonate (428 mg, 3.10 mmol) was added. The mixture was stirred at rt overnight. The reaction was stopped, and to the reaction mixture was added water (50 mL). The resulting mixture was extracted with ethyl acetate (50 mL x 2). The combined organic layers were washed with saturated brine (80 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to remove the solvent and the residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 10/1) to give the title compound as a yellow solid (317 mg, 58%).MS (ESI, pos.ion) m/z: 353.0 [M+H]1H NMR (600 MHz, CDC13) (ppm): 8.75 (s, 1H), 6.49 (d, J = 4.7 Hz, 1H), 4.63 (s, 1H), 3.76 (s, 3H), 2.50 (d, J= 5.6 Hz, 1H), 2.01 (d, J= 1.8 Hz, 1H), 1.95 (d, J= 2.5 Hz, 1H), 1.88- 1.76 (m, 2H), 1.73- 1.53 (m, 6H).

The synthetic route of 13479-88-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; REN, Qingyun; TANG, Changhua; LIN, Xiaohong; YIN, Junjun; YI, Kai; (270 pag.)WO2017/97234; (2017); A1;,
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Related Products of 935667-50-8, 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 935667-50-8 as follows.

To a -60 C solution of Example 361.0 (2.20 g, 6.3 mmol) in THF (13 mL) was added n-butyllithium (2.5 M solution in hexanes, 2.72 mL, 6.8 mmol) slowly via syringe. After 10 mm, a solution of Example 343.2 (660 mg, 5.2 mmol) in THF (5 mL) was added dropwise via cannula at-60 C. The resulting mixture was stirred at -60 C for 15 mm and was then allowed to warm to RT and stirred overnight. The reaction was quenched with saturated aqueous NH4C1 and extracted with EtOAc (3X). The combined organic layers were dried over anydrous sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography (eluent was 20-70% EtOAc in hexanes over 30 mm) to provide Example 355.01 (547 mg, 22% yield) as a red solid. LCMS-ESI (pos.) m/z: 498.0 (M+Na).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,935667-50-8, its application will become more common.

Reference:
Patent; AMGEN INC.; BROWN, Matthew; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HOUZE, Jonathan; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YEH, Wen-Chen; (815 pag.)WO2018/97944; (2018); A1;,
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Reference of 852180-74-6, Adding some certain compound to certain chemical reactions, such as: 852180-74-6, name is 3-(Pyrimidin-5-yl)benzoic acid,molecular formula is C11H8N2O2, 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 852180-74-6.

A mixture of 3-pyrimidin-5-yl-benzoic acid (100 mg, 0.50 mmol) and SOCl2 (73 mu, 1.0 mmol) was heated under reflux for 4 h. The solvent was evaporated off under reduced pressure and the residue was dissolved in DCM (5 mL) and slowly added to a mixture of 4- (chlorodifluoromethoxy)aniline (106 mg, 0.55 mmol) and TEA (140 mu, 1.0 mmol) in DCM (5 mL). The mixture was stirred at RT overnight. The solvent was evaporated off under reduced pressure and the residue was suspended in EtOAc (10 mL),filtered through a 10 muetaiota Isolute fritted cartridge and the filtrate was evaporated to dryness under reduced pressure to give the crude product which was purified by preparative HPLC to afford the title compound. LC-MS (Condition 4) tR = 1.15 min, m/z = 375.8 [M+H]+; XH-NMR (400 MHz, DMSO-d6) delta ppm 7.40 (d, J = 9.05 Hz, 2 H) 7.73 (t, J = 7.82 Hz, 1 H) 7.92 (m, 2 H) 8.06 (t, J = 6.97 Hz, 2 H) 8.37 (t, J = 1.96 Hz, 1 H) 9.24 – 9.29 (m, 3 H) 10.52 (s, 1 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. 852180-74-6, 3-(Pyrimidin-5-yl)benzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; GROTZFELD, Robert Martin; JONES, Darryl Brynley; MANLEY, Paul; MARZINZIK, Andreas; MOUSSAOUI, Saliha; PELLE, Xavier Francois Andre; SALEM, Bahaa; SCHOEPFER, Joseph; WO2013/171641; (2013); A1;,
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