Pyrimidines

Application of 165807-05-6, 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.165807-05-6, name is 4-Dimethoxymethylpyrimidin-2-ylamine, molecular formula is C7H11N3O2, molecular weight is 169.18, as common compound, the synthetic route is as follows.

Intermediate P: 1-(4-((2-Aminopyrimidin-4-yl)methoxy)naphthalen-1-yl)-3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)ureaHydrochloric acid (2M, 207 mL, 414 mmol) was added to 4-(dimethoxymethyl)pyrimidin-2-amine (68) (WO 2007/096764) (14.0 g, 83 mmol) and the mixture heated at 48° C. for 16 hr.The mixture was cooled to RT and was neutralized with solid Na2CO3 which produced a precipitate at pH 7.The suspension was diluted with EtOAc (300 mL) and the solid removed by filtration.The organic layer was separated and the aqueous layer was extracted with 1percent MeOH in THF (4*300 mL).The organics were combined, dried and then evaporated in vacuo.The residue (ca. 4.0 g) was suspended in a mixture of MeOH (100 mL), THF (100 mL) and water (100 mL) and treated with NaBH4 (1.57 g, 41.4 mmol).After stirring for 1 hr a solution of NaOH (1M, 20 mL) was added and the mixture was allowed to stand at RT for 48 hr.The solvents were evaporated to give a yellow solid which was partitioned between water (50 mL) and EtOAc (100 mL).The solid which formed at the interface was removed by filtration and the aq layer was extracted with THF (3*300 mL) then dried and evaporated to give a yellow solid.The material was suspended in THF (100 mL) and MeOH (50 mL) and absorbed onto silica gel (20 g) and subjected to column chromatography (80 g, 15percent MeOH in DCM isocratic elution) to give (2-aminopyrimidin-4-yl)methanol (69) as an off-white solid (720 mg, 7percent): m/z 126 (M+H)+ (ES+).

Statistics shows that 165807-05-6 is playing an increasingly important role. we look forward to future research findings about 4-Dimethoxymethylpyrimidin-2-ylamine.

Reference:
Patent; Charron, Catherine Elisabeth; Fenton, Robert; Crowe, Scott; Ito, Kazuhiro; Strong, Peter; Rapeport, William Garth; Ray, Keith; US2012/244120; (2012); A1;,
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Related Products of 5177-27-5 ,Some common heterocyclic compound, 5177-27-5, molecular formula is C4H3Cl2N3, 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.

3.2 g of 5-amino-2,4-dichloropyrimidine in 50 ml ethyl acetate were added to a mixture of 25 ml of saturated aqueous sodium bicarbonate solution and 25 ml of water. At room temperature, a solution of 4.9 g of 3,5-dimethyl-4-methoxybenzoyl chloride was added over a period of 15 min. The mixture was stirred intensively for 4 h. The layers were then separated, after which the aqueous layer was extracted twice with ethyl acetate. After drying over sodium sulfate and filtration, the solvent was removed under reduced pressure, giving 7.54 g of crude product. The crude product was triturated with 25 ml of isopropanol. Filtration and washing with 10 ml of isopropanol gave 2.74 g of the title compound in the form of a white solid. LC/MS (Method LC2): Rt=1.00 min; m/z=326.0; 328.0 [M+H]+ (dichloro pattern)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5177-27-5, its application will become more common.

Reference:
Patent; SANOFI; KADEREIT, Dieter; SCHAEFER, Matthias; HACHTEL, Stephanie; HUEBSCHLE, Thomas; HISS, Katrin; HAAG-DIERGARTEN, Silke; US2013/23545; (2013); A1;,
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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.51-20-7, name is 5-Bromouracil, molecular formula is C4H3BrN2O2, molecular weight is 190.9828, as common compound, the synthetic route is as follows.name: 5-Bromouracil

General procedure: To a suspension of appropriate pyrimidine base (2 equiv.) in toluene were added triethylamine (4.1 equiv.) and trimethylsilyl trifluoromethanesulfonate (6.1equiv.) and the mixture were stirred at room temperature for 1h. The silylated base solution was diluted with additional dichloromethane and this solution was then added to a solution of 10 in dichloromethane dropwise over a period of 20 min at 0C. An additional amount of triethylamine (2.1equiv.) was added dropwise to the reaction mixture to initiate the Pummerer reaction at 0C. After the reaction mixture was stirred at room temperature for 15h, the reaction mixture was quenched with saturated NaHCO3 and extracted with dichloromethane. The organic layers were washed with saturated NaHCO3 solution, water and brine, dried over MgSO4, filtered and evaporated under reduced pressure. The residue was purified on flash silica gel column chromatography (hexane:ethyl acetate=2:1) to give the beta-anomers 11a-11f.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,51-20-7, 5-Bromouracil, and friends who are interested can also refer to it.

Reference:
Article; Kim, Jin-Hee; Yu, Jinha; Alexander, Varughese; Choi, Jung Hee; Song, Jayoung; Lee, Hyuk Woo; Kim, Hea Ok; Choi, Jungwon; Lee, Sang Kook; Jeong, Lak Shin; European Journal of Medicinal Chemistry; vol. 83; (2014); p. 208 – 225;,
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Application of 89283-48-7, 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 89283-48-7, name is 4-Chloro-6-(methylthio)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a suspension of NaH (1.98 g, 50 mmol, 60% in oil) in DMSO (20 mL) is added dimethyl malonate (5.67 mL, 50 mmol) at 23C (cooled by ice-water if necessary). After the evolution of hydrogen has ceased, 4-chloro-6-methylsulfanyl-pyrimidine 2 (3.22 g, 20 mmol) is added. The reaction is further heated at 8O0C for 5 hours. The reaction mixture is then cooled to room temperature, and quenched with saturated NH4Cl solution (50 mL). The organics are extracted with ethyl acetate (3 x 60 mL). The combined organic layers are washed with brine (2x) and dried over Na2SO4, filtered and concentrated. 50 mL of hexanes are added to the residue and heated at 600C for half hour and then cooled to room temperature. The solid is filtered and washed with hexanes to afford 2-(6-methylsulfanyl- pyrimidin-4-yl)-malonic acid dimethyl ester. (If necessary, the hexanes washing can be concentrated and purified by silica gel flash chromatography eluting with ethyl acetate in hexanes from 0% to 40% to afford additional product). 1H NMR 400 MHz (DMSO-d6) Compound A delta 8.92 (s, IH), 7.53 (s, IH), 5.20 (s, I H) 3.70 (s, 6H), 2.56 (s, 3H); Compound B (tautomer of A, the structure is tentatively assigned) 8.37 (s, IH), 7.34 (s, IH), 3.66 (s, 6H), 2.48 (s, 3H).

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 89283-48-7, 4-Chloro-6-(methylthio)pyrimidine.

Reference:
Patent; IRM LLC; WO2008/8747; (2008); A1;,
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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. 3438-48-0, name is 4-Phenylpyrimidine, molecular formula is C10H8N2, 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. Recommanded Product: 4-Phenylpyrimidine

(Step 1: Synthesis of di-mu-chloro-bis[bis(4-phenylpyrimidine)iridium(III)] (abbreviation: [Ir(ppm)2Cl]2))First, into a three-neck flask equipped with a reflux pipe were put 30 mL of 2-ethoxyethanol, 10 mL of water, 0.67 g of a ligand 4-phenylpyrimidine (abbreviation: Hppm), 0.50 g of iridium chloride (IrCl3-HCl H20), and the air in the three-neck flask was replaced with nitrogen. After that, the mixture was heated and refluxed for 13 hours to be reacted. The reacted solution was cooled naturally to room temperature and filtered. The substance obtained by the filtration was washed with ethanol to give a dinuclear complex [Ir(ppm)2Cl]2 (red powder, yield of 42 %). A synthesis scheme (d-1) of Step 1 is shown below.

With the rapid development of chemical substances, we look forward to future research findings about 3438-48-0.

Reference:
Patent; SEMICONDUCTOR ENERGY LABORATORY CO., LTD.; INOUE, Hideko; YAMAGUCHI, Tomoya; SHITAGAKI, Satoko; USHIKUBO, Takahiro; SEO, Satoshi; YAMADA, Yui; NOWATARI, Hiromi; WO2012/53627; (2012); A1;,
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Pyrimidine – Wikipedia

Application of 1254710-16-1, Adding some certain compound to certain chemical reactions, such as: 1254710-16-1, name is 8-Bromo-7-chloro-2-phenyl-[1,2,4]triazolo[1,5-c]pyrimidine,molecular formula is C11H6BrClN4, 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 1254710-16-1.

General procedure: A mixture of 5a (0.16 g, 0.5 mmol), the appropriate amine (1.5mmol, 3.0 equiv), and Et3N (0.51 g, 5 mmol) in anhydrous MeOH(15 mL) was stirred under reflux for 24 h until full consumption ofthe substrates. The progress of the reaction was monitored by TLC(eluent: PE-EtOAc, 3:1). Then, the mixture was concentrated underreduced pressure. The residue was directly subjected to columnchromatography on silica gel using PE-EtOAc (8:1) as the eluent toafford, respectively, the desired 7,8-bis(amino)-substituted[1,2,4]triazolo[1,5-c]pyrimidines 6g and 6h.

According to the analysis of related databases, 1254710-16-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tang, Caifei; Wang, Chao; Li, Zhiming; Wang, Quanrui; Synthesis; vol. 46; 20; (2014); p. 2734 – 2746;,
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Synthetic Route of 17119-73-2, 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 17119-73-2, name is 4-Chloro-6-methyl-2-(methylthio)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

[00195] Ethyl 3-iodo-i-methylcyclopentanecarboxylate (5.60 g, 19.9 mmol) was dissolved in dimethylacetamide (66 mL) in a pressure vessel under a stream of nitrogen. Rieke Zinc (28.6 mL of a 5Omg/mL suspension in THF, 21.8 mmol) was added quickly via syringe. The vessel was capped and stirred at ambient temperature for 15 minutes. The vessel was opened under a stream of nitrogen and 4-chloro-6-methyl-2- (methylthio)pyrimidine (4.16 g, 23.8 mmol) was added followed by PdCl2dppf (1.09 mg, 1.49 mmol). The vessel was capped and heated to 80 C for 2 h. The reaction mixture was then cooled to room temperature, diluted with ethyl acetate, and filtered through celite. The filtrate was transferred to a separatory funnel and washed with water (3x), brine, and dried over sodium sulfate. The dried solution was filtered, and the filtrate was concentrated. The residue was purified by flash-column chromatography on silica gel (gradient elution, 0 to 100% ethyl acetate-hexanes) to give ethyl 1-methyl- 3 -(6-methyl-2-(methylthio)pyrimidin-4-yl)cyclopentane- 1 -carboxylate (2.1 g, 36%) as a mixture of cis and trans isomers. The isomers were separated by preparative HPLC (column: Phenomenex Gemini C18 250*5Omm*10 um; mobile phase: 45-70% water [0.05% ammonia hydroxide v/v]-ACN) to give ethyl (1R,3R and 1S,3S)-1-methyl-3-(6- methyl-2-(methylthio)pyrimidin-4-yl)cyclopentane- 1 -carboxylate (700 mg) as a colorless oil. MS (ES+) C,5H22N2025 requires: 294, found: 295 [M+H]. ?H NMR (400 IVIFIz, CDC13): ppm 6.67 (s, 1H), 4.17 (q, J= 7.2 Hz, 2H), 3.27-3.18 (m, 1H), 2.61- 2.53 (m, 4H), 2.42 (s, 3H), 2.30-2.23 (m, 1H), 2.14-2.05 (m, 1H), 2.02-1.91 (m, 1H),1.8 1-1.72 (m, 2H), 1.38 (s, 3H), 1.29 (t, J= 7.2 Hz, 3H).

According to the analysis of related databases, 17119-73-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; BRUBAKER, Jason, D.; DIPIETRO, Lucian, V.; (105 pag.)WO2018/22761; (2018); A1;,
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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. 49845-33-2, name is 2,4-Dichloro-5-nitropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 49845-33-2

(a) ChlorobonitrQineTo a solution of 2,4-dichloro-5-nitro-pyrimidine (1.00 g; 5.2 mmol) in methanol (30 mL) was added dropwise a solution of sodium methoxide (278 mg, 5.2 mmol) in methanol (5mL) at-10 C. The reaction mixture was stirred for 10 minutes at -10 C. Acetic acid (5 mL) wasadded and the mixture was allowed to warm to room temperature. After evaporation of themixture, the residue was partitioned between 5% NaHCO3-solution and ethyl acetate. The ethyl acetate layer was washed with water, brine, dried over sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography (heptane/ethyl acetate 4/1 v/v%) to obtain 281.9 mg (29%) of 2-chloro-4-methoxy-5-nitro-pyrimidine.

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, 49845-33-2, 2,4-Dichloro-5-nitropyrimidine.

Reference:
Patent; NETHERLANDS TRANSLATIONAL RESEARCH CENTER B.V.; DE MAN, Adrianus Petrus Antonius; BUIJSMAN, Rogier Christian; STERRENBURG, Jan Gerard; UITDEHAAG, Joost Cornelis Marinus; DE WIT, Joeri Johannes Petrus; ZAMAN, Guido Jenny Rudolf; WO2015/155042; (2015); A1;,
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Pyrimidine – Wikipedia

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.504-17-6, name is 4,6-Dihydroxy-2-mercaptopyrimidine, molecular formula is C4H4N2O2S, molecular weight is 144.1518, as common compound, the synthetic route is as follows.Application In Synthesis of 4,6-Dihydroxy-2-mercaptopyrimidine

General procedure: A mixture of aldehyde (0.25 mmol), 2-thiobarbituric acid(0.5 mmol), ammonium acetate (0.3 mmol) and CuFe2O4 (10 mol%)in distilled H2O was stirred for an appropriate time. After completionof the reaction (monitored by TLC), the resulted precipitatewasfiltered and dissolved in hot methanol and the catalyst was separatedand collected by an external magnetic and washed withacetone and EtOH several times and dried in an oven at 70 C toreuse in next reactions. The pure solid product was obtained viaevaporation the 2/3 of methanol and filtration. The solid productwas recrystallized from water/ethanol as solvent to afford the pureproducts. All of the products were identified by physical andspectroscopic data. White powder; M.P: 240 C decompose. IR (KBr) n (cm1): 3432(NH), 3108 (CeH, sp2 stretch), 1623, 1687 (C]O), 1433, 1544 (C]C,Ar). 1H NMR (DMSO-d6, 400 MHz) d (ppm): 6.01 (s, 1H), 6.91e7 (m,3H), 7.08e7.12 (m, 4H), 11.49e11.75 (m, 4H), 17 (s, 1H). 13C NMR(DMSO-d6, 100 MHz) d (ppm): 26.88, 95.44, 115.26, 123.60, 127.61,130.05, 130.48, 159.60, 162.03, 163.32, 173.24. Anal. Calcd forC15H12FN5O2S2: C, 47.74; H, 3.20; N, 18.56, %; Found C, 47.76; H,3.24; N, 18.60%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,504-17-6, 4,6-Dihydroxy-2-mercaptopyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Naeimi, Hossein; Didar, Asieh; Journal of Molecular Structure; vol. 1137; (2017); p. 626 – 633;,
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Synthetic Route of 187035-79-6, 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. 187035-79-6, name is Ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate. A new synthetic method of this compound is introduced below.

The intermediate 8-(((tert-butyldiphenylsilyl)oxy)methyl)- 1 -isopropyl-7- (methylsulfonyl)- l,2,3,4-tetrahydropyrazino[l,2-a]indole was prepared following a procedure analogous to that described in Preparation 4. The mixture of compound 8-(((tert- butyldiphenylsilyl)oxy)methyl)- l-isopropyl-7-(methylsulfonyl)-l, 2,3,4- tetrahydropyrazino[l,2-a] indole (0.19 mmol), ethyl 2-chloro-4-(trifluoromethyl)pyrimidine- 5-carboxylate (97 mg, 0.38 mmol) and DIEA (100 mu,, 0.57 mmol) in j-PrOH / CH2C12 (1 mL / 0.5 mL) was stirred at 50C for 8 h. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel eluting with EtOAc/hexanes (1/1) to give racemic ethyl 2-(8-(hydroxymethyl)- l-isopropyl-7-(methylsulfonyl)-3,4- dihydropyrazino[ 1 ,2-a]indol-2( lH)-yl)-4-(trifluoromethyl)pyrimidine-5-carboxylate. LC- MS m/z 563 [M+Na]+. 1H NMR (400 MHz, CD3OD): delta 9.31 (s, 1H), 8.11 (s, 1H), 7.80 (s, 1H), 6.55 (s, 1H), 6.02 – 5.92 (m, 1H), 5.23 – 5.17 (m, 1H), 5.07 (s, 2H), 4.52 – 4.47 (m, 1H), 4.34 (q, J = 7.2 Hz, 2H), 4.19 – 4.06 (m, 1H), 4.00 – 3.93 (m, 1H), 3.27 (s, 3H), 2.42 – 2.32 (m, 1H), 1.36 (t, J = 7.2 Hz, 3H), 1.18 (d, J = 6.8 Hz, 3H), 1.03 (d, J = 6.8 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,187035-79-6, Ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; DONG, Chengguo; FAN, Yi; LEFTHERIS, Katerina; LOTESTA, Stephen; SINGH, Suresh, B.; TICE, Colin; ZHAO, Wei; ZHENG, Yajun; ZHUANG, Linghang; WO2013/138568; (2013); A1;,
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