Tag: M.W:100-200

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.1683-75-6, name is 2-Amino-4-chloro-5-fluoropyrimidine, molecular formula is C4H3ClFN3, molecular weight is 147.54, as common compound, the synthetic route is as follows.Formula: C4H3ClFN3

[00306] A mixture of 4-chloro-5-fluoropyrimidin-2-amine (3) (O. lg, 0.64 mmol) and 3,4- dichlorophenyl isocyanate (0.24g, 1.29 mmol) in dioxane (3 mL) was heated overnight at 90 C. The mixture was chromatographed in 0-60% ethyl acetate in hexanes to afford the title product (167). (75mg, 35%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1683-75-6, 2-Amino-4-chloro-5-fluoropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; CURTANA PHARMACEUTICALS, INC.; BEATON, Graham; MCHARDY, Stanton F.; LOPEZ JR., Ambrosio; CAMPOS, Bismarck; WANG, Hua-Yu Leo; (143 pag.)WO2019/169112; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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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Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
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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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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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Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
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. 26452-81-3, name is 4-Chloro-6-methoxypyrimidine, molecular formula is C5H5ClN2O, 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. Quality Control of 4-Chloro-6-methoxypyrimidine

EXAMPLES 7-12 General Procedure for Conversion of 4-chloro-6-methoxypyrimidine (CMP) to 4,6-dichloropyrimidine (DCP): The reaction vessel is a Morton-type flask fitted with a heating mantle, a mechanical agitator, a temperature probe, a phosgene dip pipe (which also serves as a nitrogen inlet when phosgene is not being introduced to the reactor), and a dry ice condenser. The dry ice condenser is vented into a caustic scrubber. The reactor is charged with CMP, solvent, and catalyst. The agitator is started and the mixture is heated to 100°-110° C. When this temperature range is reached, phosgene gas is introduced subsurface to the reaction mixture via the dip pipe. Phosgene addition is continued over 3-5 hours. During the addition, phosgene escaping the reaction mixture is condensed by the dry ice condenser and returned to the reaction mixture. This reflux of phosgene begins shortly after the phosgene addition is begun, and continues throughout the course of the reaction.

With the rapid development of chemical substances, we look forward to future research findings about 26452-81-3.

Reference:
Patent; Doyle, Timothy John; Wehrenberg, Peter Karl; Standen, Michael Charles Henry; US2002/42514; (2002); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 43212-41-5, Adding some certain compound to certain chemical reactions, such as: 43212-41-5, name is 2,4-Dichloro-6-methoxypyrimidine,molecular formula is C5H4Cl2N2O, 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 43212-41-5.

This product is mixed with morpholine in THF and stirred at 20-25 to give 6-methoxy-2-morpholino-4-chloropyrimidine.

According to the analysis of related databases, 43212-41-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Upjohn; US5120843; (1992); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia