Pyrimidines

Electric Literature of 7752-78-5 ,Some common heterocyclic compound, 7752-78-5, molecular formula is C5H5BrN2, 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.

5-Bromo-1-(2-methylpyrimidin-5-yl)-1H-indole (13A) 5-Bromo-2-methylpyrimidine (0.971 g, 5.61 mmol) was added to a solution of 5-bromo-1H-indole (1 g, 5.1 mmol) and copper(I) bromide (0.073 g, 0.51 mmol) in DMF (10 mL) followed by potassium carbonate (1.762 g, 12.75 mmol), and the resulting mixture was stirred at 100° C. for 10 min. NaOH (0.153 g, 3.83 mmol) and copper(II) acetate (0.009 g, 0.051 mmol) were added at 110° C., and the reaction mixture was stirred for 16 h. Insoluble solids were filtered, and the filtrate was concentrated. The residue was partitioned between ethyl acetate and water. Separated organic layer was dried over sodium sulphate and filtered. The filtrate was concentrated in vacuo and purified by flash chromatography using 10percent ethyl acetate in hexane to afford the title compound (0.25 g, 16percent) as an off-white solid. 1H NMR (300 MHz, CDCl3): delta 8.81 (s, 2H), 7.83 (d, J=1.5 Hz, 1H), 7.36 (dd, J1=1.8 Hz, J2=8.7 Hz, 1H), 7.33-7.26 (m, 2H), 6.71 (d, J=3.3 Hz, 1H), 2.82 (s, 3H). ESI-MS m/z=288 (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,7752-78-5, its application will become more common.

Reference:
Patent; GlaxoSmithKline LLC; CHEUNG, Mui; TANGIRALA, Raghuram S.; US2014/148437; (2014); A1;,
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. 157335-97-2, name is 5-Bromo-4,6-dimethylpyrimidine, the common compound, a new synthetic route is introduced below. Recommanded Product: 157335-97-2

Step 3. Synthesis of 4-[4-(4,6-dimethylpyrimidin-5-yl)-3-fluorophenoxy]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[3,2-c]pyridine (C14) A mixture of C13 (427 mg, 0.881 mmol), 5-bromo-4,6-dimethylpyrimidine (150 mg, 0.802 mmol), tris(dibenzylideneacetone)dipalladium(0) (147 mg, 0.160 mmol), tricyclohexylphosphine (90 mg, 0.32 mmol) and potassium phosphate (341 mg, 1.61 mmol) in 1,4-dioxane (4 mL) containing 5 drops of water was heated at 120 C. for 2 hours under microwave irradiation. The mixture was filtered, the filtrate was concentrated under reduced pressure, and the residue was purified by preparative thin layer chromatography on silica gel (Eluent: ethyl acetate) to give the product, which was used without further purification. Yield: 180 mg, 0.387 mmol, 48%. LCMS m/z 465.3 [M+H+].

The synthetic route of 157335-97-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC; DAVOREN, JENNIFER ELIZABETH; DOUNAY, AMY BETH; EFREMOV, IVAN VIKTOROVICH; GRAY, DAVID LAWRENCE FIRMAN; MENTE, SCOT RICHARD; O’NEIL, STEVEN VICTOR; ROGERS, BRUCE NELSEN; SUBRAMANYAM, CHAKRAPANI; ZHANG, LEI; US2014/128374; (2014); A1;,
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Application of 147118-37-4, Adding some certain compound to certain chemical reactions, such as: 147118-37-4, name is N-(4-(4-Fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide,molecular formula is C16H18FN3O3S, 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 147118-37-4.

Step D: Titanium tetrachloride (1M in dichloromethane, 12.67 mL) was added dropwise to a solution of 4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)-5-pyrimidinecarbardehyde (2.13 g) (compound of formula (III-a)) in dry THF (60 mL) at 0C. After stirring for 15 minutes, a solution of compound of formula (II, PG=TBDMS, Z=OMe) (2 g) in dry THF (20 mL) and subsequently a solution of N-methylmorpholine (2.64 mL) in dry THF (20 mL) were slowly added. The reaction mixture was stirred at 0C for 3h, then quenched with water (40 mL) and extracted with EtOAc (3×40 mL). The combined organic layers were dried under vacuum and the resulting oil was purified via chromatographic column on silica gel (hexane/EtOAc 9:1) to give the 2.5 g of the corresponding racemic product of formula (I-a, PG=TBDMS, Z=OMe) (Molar yield = 68% yield). [0125] The 1 N-NMR spectrum is the same of that of the product of Example 4.

According to the analysis of related databases, 147118-37-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F.I.S.- Fabbrica Italiana Sintetici S.p.A.; De Lucchi, Ottorino; Tartaggia, Stefano; Ferrari, Clark; Galvagni, Marco; EP2769979; (2014); A1;,
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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. 4318-56-3, name is 6-Chloro-3-methylpyrimidine-2,4(1H,3H)-dione, the common compound, a new synthetic route is introduced below. COA of Formula: C5H5ClN2O2

a) 6-Chloro-3-methyl-1-(2-methylpropyl)-1H-pyrimidine-2,4(1H,3H)-dione. A mixture of 6-chloro-3-methyl-1H-pyrimidine-2,4(1H,3H)-dione (J. Amer. Chem. Soc., 1980, 102, 5036) (27.85 g), 1-iodo-2-methylpropane (21.9 ml) and potassium carbonate (26.36 g) in anhydrous dimethylformamide (110 ml) was stirred at 90 C., under nitrogen for 40 hours. The reaction mixture was cooled to room temperature and diluted with water (800 ml). Brine (100 ml) was added and the mixture was extracted with ether (2*500 ml). The organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residual oil was triturated with ether and the resulting crystals were filtered, washed with ether and dried in vacuo to give the subtitle compound (7.38 g). The mother liquors were evaporated under reduced pressure and purified by column chromatography over silica eluding with isohexane:ether (1:1) to give further subtitle compound (6.90 g). 1H NMR (CDCl3) delta 0.96 (6H, d), 2.10-2.24 (1H, m), 3.34 (3H, s), 3.90 (2H, d), 5.92 (1H, s).

The synthetic route of 4318-56-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AstraZeneca AB; US6300334; (2001); B1;,
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Pyrimidine – Wikipedia

Related Products of 24415-66-5 ,Some common heterocyclic compound, 24415-66-5, molecular formula is C6H5ClN4, 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.

General procedure: A mixture of chloro compound (50 mg) and amine derivative (2 equiv.) in PEG 400 (2 mL) wasstirred at 120 C for 5 min. After completion the reaction was then cooled to room temperature. DCM and water were added and the phases were separated. The aqueous phase was extracted withDCM and the organic phase was dried and filtered. The removal of solvent gave the product as solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,24415-66-5, its application will become more common.

Reference:
Article; Campos, Joana F.; Loubidi, Mohammed; Scherrmann, Marie-Christine; Berteina-Raboin, Sabine; Molecules; vol. 23; 3; (2018);,
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Synthetic Route of 1260088-72-9, 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.1260088-72-9, name is 2,4-Dichloro-7,7-dimethyl-5,7-dihydrofuro[3,4-d]pyrimidine, molecular formula is C8H8Cl2N2O, molecular weight is 219.0679, as common compound, the synthetic route is as follows.

General procedure: A mixture of 2,4-dichloro-7,7-dimethyl-5,7-dihydrofuro[3,4-d]pyrimidine7 (257mg, 1.173 mmol), 1H-pyrazolo[4,3-c]pyridin-3-amine (291 mg, 1.735 mmol), N,N-diisopropylethylamine (0.40 mL, 2.3 mmol) and N,N-dimethylformamide (4.0 mL) was heated at 70 C for 2 hours. The reaction mixture was diluted with ethyl acetate, washed with water (2x) and brine, dried over magnesium sulfate, filtered, and evaporated in vacuo. The crude product was purified via flash chromatography on silica gel (24 silica, solvent gradient: 0-100% ethyl acetate in dichloromethane followed by 10% methanol indichloromethane) to yield 176.7 mg of the title compound.

Statistics shows that 1260088-72-9 is playing an increasingly important role. we look forward to future research findings about 2,4-Dichloro-7,7-dimethyl-5,7-dihydrofuro[3,4-d]pyrimidine.

Reference:
Article; Hanan, Emily J.; Baumgardner, Matt; Bryan, Marian C.; Chen, Yuan; Eigenbrot, Charles; Fan, Peter; Gu, Xiao-Hui; La, Hank; Malek, Shiva; Purkey, Hans E.; Schaefer, Gabriele; Schmidt, Stephen; Sideris, Steve; Yen, Ivana; Yu, Christine; Heffron, Timothy P.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 2; (2016); p. 534 – 539;,
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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 73418-87-8, name is 2-(Trifluoromethyl)pyrimidin-5-amine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-(Trifluoromethyl)pyrimidin-5-amine

Into a 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen,was placed 2-(trifluoromethyl)pyrimidin-5-amine (2 g, 12.3 mmol) in acetonitrile (20 mL), tothis stirred solution was added NBS (2.62 g, 14.7 mmol). The resulting solution was stirred for 12 h at RT. The resulting solution was diluted with 40 mL of water. The resulting solution was extracted with 2×30 mL of dichloromethane and concentrated. The residue was eluted from silica gel with ethyl acetate/petroleum ether (1:50 to 1:20). This resulted in 1.6 g (53.9%) of thetitle compound as a brown solid. MS-ESI: 242/244 [M+1]

With the rapid development of chemical substances, we look forward to future research findings about 73418-87-8.

Reference:
Patent; IFM TRE, INC.; GLICK, Gary; ROUSH, William R.; VENKATRAMAN, Shankar; SHEN, Dong-Ming; GHOSH, Shomir; KATZ, Jason; SEIDEL, Hans Martin; FRANCHI, Luigi; WINKLER, David Guenther; OPIPARI JR., Anthony William; (637 pag.)WO2019/23145; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 3932-97-6, Adding some certain compound to certain chemical reactions, such as: 3932-97-6, name is 2,4-Dichloro-5-(trifluoromethyl)pyrimidine,molecular formula is C5HCl2F3N2, 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 3932-97-6.

5 g (23 mmol) 2,4-dichloro-5-trifluoromethyl-pyrimidine is dissolved in 40 mL THF, the solution is adjusted to -25 C. and 1.8 g (25.3 mmol, 1.1 eq) sodium thiomethoxide is added. The mixture is stirred for 1 h at -25 C. and then without cooling stirred overnight at RT. Then it is diluted with dichloromethane and washed 3× with 1 N HCl. The organic phase is dried on magnesium sulphate and evaporated down in vacuo. The crude product is purified by column chromatography (silica gel, cyclohexane/dichloromethane; from 90/10 to 80/20% in about 20 min). 1.56 g (6.8 mmol, 30%) of the product A-3 and 1.46 g (6.4 mmol, 28%) of the product A-2 are isolated as colourless oils. In addition 0.24 g (4%) of 2,4-bis-methylsulphanyl-5-trifluoromethyl-pyrimidine may be isolated as a colourless solid. product A-3 product A-2 Rf (cHex:CH2Cl2 1:1) 0.48 0.40 The structural analysis is carried out by chemical derivatisation and subsequent NMR spectroscopy. For this, A-2 and A-3 are first of all dehalogenated separately in THF at 100 C., 5 bar H2, Pd/C and Pd(OH)2 in a ratio of 1:1 in each case. Thanks to the different symmetry characteristics of the products formed it is possible to identify the regioisomers clearly.

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. 3932-97-6, 2,4-Dichloro-5-(trifluoromethyl)pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zahn, Stephan Karl; Boehmelt, Guido; Mantoulidis, Andreas; Reiser, Ulrich; Treu, Matthias; Guertler, Ulrich; Schoop, Andreas; Solca, Flavio; Tontsch-Grunt, Ulrike; Brueckner, Ralph; Reither, Charlotte; Herfurth, Lars; Kraemer, Oliver; Stadtmueller, Heinz; Engelhardt, Harald; US2007/32514; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 89466-39-7, 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. 89466-39-7, name is 4-Chloro-6-methoxy-2-methylpyrimidine. A new synthetic method of this compound is introduced below.

1,1,1 ,2,2,2-Hexamethyl-distannane (620 mg, 1.892 mmol) and tetrakis(triphenylphosphine)palladium (219 mg, 0.189 mmol)were added to a solution of 4-chloro-6-methoxy-2-methylpyrimidine (300 mg, 1.892 mmol) in 1,4-dioxane (3 mL). The reaction mixture was degassed with nitrogen 3 times and stirred for 1 h at 100C under and atmosphere of nitrogen. The reaction mixture was used in the next step directly without further purification. MS = 285.0/287.0/289.0 (+ESI).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89466-39-7, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SHEN, Dong-Ming; WILSON, Jonathan, E.; MCCRACKEN, Troy; (95 pag.)WO2016/179059; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 355806-00-7, (3R,5S,6E)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-[(methanesulfonyl) methylamino]pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoic acid tert-butyl ester, 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, Computed Properties of C26H36FN3O6S, blongs to pyrimidines compound. Computed Properties of C26H36FN3O6S

(2) Preparation of sodium (E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl) amino]pyrimidin-5-yl]-(3R,5S)-3,5-dihydroxy-hept-6-enoate (compound IV) To a 5 L four-necked flask, 2 L (10 mL/g) of acetonitrile and 200 g (1 mol) of tert-butyl 6-[(1E)-2-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methanesulfonyl)amino]-5-pyrimidinyl]vinyl]-2,2-dimethyl-1,3-dioxane-4-acetate (compound III) were added, and stirred to homogeneity, followed by adding 14.8 g (0.02 mol, calculated from titrated content) of an aqueous solution of hydrochloric acid having a mass percentage concentration of 0.06%. The system was warmed up to 35 C. and stirred at the same temperature for 5 hours until compound III was completely consumed. To the reaction system was added dropwise 32.5 g (1.1 mol) of an aqueous solution of sodium hydroxide having a mass percentage concentration of 4%, and stirred at 20 C. for 7 hours until the dihydroxy ester intermediate produced in the first phase was completely consumed. The system was concentrated to remove acetonitrile, followed by adding 2 L (10 mL/g) of purified water, and stirred to clearness. The system was extracted three times with 400 mL (2 mL/g) of methyl tert-butyl ether. The aqueous phase was further concentrated until no organic solvent was left, to give the an aqueous solution of the product, sodium (E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl]-(3R,5S)-3,5-dihydroxy-hept-6-enoate (compound IV), with a purity of >98% and a yield of 97%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,355806-00-7, (3R,5S,6E)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-[(methanesulfonyl) methylamino]pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoic acid tert-butyl ester, and friends who are interested can also refer to it.

Reference:
Patent; Asymchem Laboratories (Tianjin) Co., Ltd.; Asymchem Life Science (Tianjin) Co., Ltd.; Tianjin Asymchem Pharmaceutical Co., Ltd.; Asymchem Laboratories (Fuxin) Co., Ltd.; Jilin Asymchem Laboratories Co., Ltd.; HONG, Hao; GAGE, James; LI, Jiuyuan; SHEN, Litao; ZHANG, Lei; DONG, Changming; (12 pag.)US2017/22169; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia