Category: pyrimidines

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 56741-95-8, name is 2-Amino-5-bromo-4-hydroxy-6-phenylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C10H8BrN3O

To a solution of 35 (0.25 g, 0.94 mmol) in DMF (8 mL) was added NEt3 (0.14 mL, 0.99 mmol) and diethyl pyrocarbonate (0.27 mL, 1.89 mmol). The reaction mixture was maintained at 65 C. for 20 h. The solvent was removed and the residue treated with DCM. The resulting mixture was filtered to remove the remaining starting material 35 and the filtrate washed with aqueous NaHCO3, brine and dried (MgSO4). The filtrate was concentrated and purified by HPLC (Thomson ODS-A 100A 5mu 150×21.2 mm column; flow rate=30 mL/min; CH3CN with 0.05% TFA (A), Water with 0.05% TFA (B); Make up pump flow=0.9 mL/min; Make up pump mobile phase; MeOH with 0.05% TFA using a gradient system as follows: t=0; 15% A, 85% B; t=3.0 min; 15% A, 85% B; t=9.5 min; 70% A, 30% B; t=10.0 min; 100% A, 0% B; t=12.0 min; 100% A, 0% B; t=12.5 min; 15% A, 85% B; t=15.0 min; 15% A, 85% B.) to afford 54 mgs of 36 (17%) as a clear oil: 1H NMR (400 MHz, CDCl3)delta 7.66 (m, 1H), 7.44 (m, 3H), 4.26 (q, J=7.6 Hz, 2H), 1.32 t, J=6.8 Hz, 3H); MS (+)-ES [M]+338.1 [M+2]+340.0 m/z. Elemental analysis for C13H12BrN3O3: calc’d: C, 46.17; H, 3.58; N, 12.43; found: C, 46.43; H, 3.74; N, 11.95.

With the rapid development of chemical substances, we look forward to future research findings about 56741-95-8.

Reference:
Patent; Averett, Devron R.; US2005/54590; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 63155-11-3 ,Some common heterocyclic compound, 63155-11-3, molecular formula is C8H10N2O2, 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 mixture of ethyl 2-pyrimidin-2-ylacetate (900 mg, 5.42 mmol) in THF (20 mL) was added LDA (3.25 mL, 6.5 mmol) at -78 C, then the mixture was stirred at -78 C for 2 hours. To the mixture was added iodomethane (922.46 mg, 6.5 mmol), then the mixture was stirred at -78 C to 20 C for 3 hours. The mixture was quenched with sat. NH4C1 (30 mL), then the mixture was extracted with EtOAc (50 mL x 2). The combined organic phase was washed with water (20 mL) and brine (20 mL), dried over Na2S04, filtered and concentrated to give the crude product. The crude product was purified by flash chromatography on silica gel (EtOAc in PE = 0% to 20% to 45%) to give the product (730 mg, 4.05 mmol, 75% yield) as oil. 1H NMR (CDC13, 400MHz) deltaH = 8.72 (d, 2H), 7.19 (t, 1H), 4.19 (q, 2H), 4.14 – 4.07 (m, 1H), 1.62 (d, 3H), 1.22 (t, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,63155-11-3, its application will become more common.

Reference:
Patent; PRAXIS PRECISION MEDICINES , INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (244 pag.)WO2018/148745; (2018); 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. 34415-10-6, name is 2-Methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid, the common compound, a new synthetic route is introduced below. COA of Formula: C6H6N2O3

Example 1592-Methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid [(5R,7R)-2-(3,5-difluoro-phenyl)-1-oxo-2-aza-spiro[4.5]dec-7-yl]amide Example 159 was made from intermediate 36 via the process of Scheme 1, supra, as follows:To a solution of intermediate 36 (5R,7R)-7-amino-2-(3,5-difluoro-phenyl)-2-aza-spiro[4.5]decan-1-one (80 mg, 0.28 mmol), triethylamine (0.16 mL, 1.14 mmol) in DMF (2.0 mL) was added 6-hydroxy-2-methyl-pyrimidine-4-carboxylix acid (49 mg, 0.32 mmol), HOBt (51 mg, 0.38 mmol) and EDCI (73 mg, 0.38 mmol). The mixture was stirred at rt overnight. The solvent was removed with Genevac, and the resulting residue was purified with spectrometry (RP-HPLC/MS) purification system (Gradient: acetonitrile in water, 25-95% in 3.9 minutes with a cycle time of 5 min. Flow rate: 100 mL/min. Mobile phase additive: 48 mM of ammonium formate. Column: Inertsil C18, 30×50 mm, 5 um particle size) to afford 26 mg (22%) of the title compound 2-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid [(5R,7R)-2-(3,5-difluoro-phenyl)-1-oxo-2-aza-spiro[4.5]dec-7-yl]amide. 1H NMR (400 MHz, CDCl3) delta 13.0 (bs, 1H), 7.94 (d, J=8.4 Hz, 1H), 7.25-7.32 (m, 2H), 7.14 (s, 1H), 6.56-6.63 (m, 1H), 4.02-4.12 (m, 1H), 3.73-3.80 (m, 2H), 2.52 (s, 3H), 2.04-2.26 (m, 3H), 1.86-1.95 (m, 2H), 1.34-1.80 (m, 5H). ESI-MS m/z: 417 (M+H)+.

The synthetic route of 34415-10-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; US2011/98299; (2011); A1;,
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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. 3438-61-7, name is 5-Amino-4-methylpyrimidine. A new synthetic method of this compound is introduced below., category: pyrimidines

To a solution of the reactant (109 mg, 1.0 mmol) in toluene (1.5 mL) was added acetic anhydride (0.2 mL, 2.10 mmol), acetic acid (0.2 mL, 3.5 mmol) followed by potassium acetate (196 mg, 2.0 mmol). The mixture was heated to reflux and isopentyl nitrire (0.168 mL, 1.25 mmol) in toluene (0.3 mL) was added. After 2 hours, the mixture was poured into water (20 mL). The solution was made basic by addition of Na2C03 solid. The solution was extracted with ethyl acetate (2×50 mL) and the combined organic extracts were washed with brine (50 mL), dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography (eluant:petroleum ether: ethyl acetate = 1 :2) to afford product product (32 mg, 0.266 mmol, Yield=27%) as yellow solid. 1H NMR (400 MHz, d6-DMSO) 5(ppm): 13.91 (1H, br), 9.35 (1H, s), 9.04 (1H, s), 8.45 (1H, s).

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, 3438-61-7, 5-Amino-4-methylpyrimidine.

Reference:
Patent; SAGE THERAPEUTICS, INC.; BOTELLA, Gabriel Martinez; HARRISON, Boyd L.; ROBICHAUD, Albert Jean; SALITURO, Francesco G.; BERESIS, Richard Thomas; WO2014/169832; (2014); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 289042-10-0, N-(5-((Diphenylphosphoryl)methyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide, 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, Recommanded Product: N-(5-((Diphenylphosphoryl)methyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide, blongs to pyrimidines compound. Recommanded Product: N-(5-((Diphenylphosphoryl)methyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide

Sodium bis (trimethylsilyl) amide (1 M in tetrahydrofuran, 23 mi) is added dropwise, AT-74C, to a suspension of the compound of formula (38) (12 g, 22.3 MMOL) in tetrahydrofuran (130 M .). STIRRING is carried out at-74C for 1 hour and then a solution of the compound of formula (40) (6.9 g, 26.8 MMOI) in toluene (28 ML) is added dropwise. Stirring is then carried out AT-74C for 1 hour, then warming to 10C over the course of 1 hour and stirring for a further 1 hour at that temperature. A mixture of acetic acid (2 ml) and water (8.4 ML) is added, at 10C, to the resulting yellow suspension and stirring is carried out at room temperature for 5 minutes. The tetrahydrofuran is then distilled off, and, at 40C, 45 ml of water are added to the reaction mixture and vigorous stirring is carried out for 5 minutes. The aqueous phase is separated off and a solution of sodium hydrogen carbonate (2.27 G) in water (45 ml) is added to the organic phase. Vigorous stirring is again carried out for 5 minutes and then the aqueous phase is removed again. The organic phase is diluted with 250 ML of toluene, washed successively with water and saturated sodium chloride solution and dried (using NA2SO4). The salt mixture is filtered off and the filtrate is concentrated by evaporation. The concentrated residue is then purified by column chromatography on silica gel (hexane: ethyl acetate 8: 1). 2.59 G (61 %) of the desired product (39) can be obtained in the form of colourless crystals. ‘H NMR (300 MHz, CDCI3) : 0.91-1. 08 (m, 1H) ; 1.20 (d, J = 6. 7 HZ, 6H); 1. 24 (S, 3H); 1. 38 (S, 9H); 1.41 (S, 3H); 1.41-1. 56 (m, 1 H) ; 2.21 (dd, J = 15. 2, 7. 9, 1 H) ; 2. 35 (dd, J = 15. 0, 5. 0 HZ, 1H) ; 3. 27-3. 37 (m, 1H) ; 3. 43 (S, 3H); 3.52 (S, 3H); 4.17-4. 24 (m, 1H) ; 4. 47-4. 53 (m, 1H) ; 5.43 (dd, J = 16.4, 5.5 Hz, 1H) ; 6.55 (dd, J = 16.1, 0.8 Hz, 1H) ; 7.24 (dd, J = 8.8, 8.8 HZ, 2H); 7.65 (dd, J = 8.8, 5.6 Hz, 2H). 13C NMR (75 MHz, CDCI3) : 18.7, 20.6, 20.7, 27.0, 29.0, 30.9, 32.0, 35.0, 41.3, 41.4, 64.8, 68.1, 79.6, 97.7, 113.7 (JCF = 21.7 Hz), 120.0, 122.0, 131. 0 (JCF = 8.4 Hz), 133.2 (JCF = 3.2 Hz), 136.3, 156.0, 162.0 (JCF = 249 Hz), 162.2, 168.8, 173.6.

The synthetic route of 289042-10-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CIBA SPECIALTY CHEMICALS HOLDING INC.; WO2004/103977; (2004); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 56621-91-1, 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. 56621-91-1, name is 5-Amino-2-bromopyrimidine, molecular formula is C4H4BrN3, 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.

To a solution of 2-bromopyrimidin-5-amine (3.0 g, 23 mmol) in fert-BuOH (46 mL) was added Boc20 (8.0 mL, 34 mmol). The reaction was stirred at 60 C for two days, after which additional Boc20 (8.0 mL, 34 mmol) was added and the reaction was kept at 60 C for two days. Upon completion, the solvent was evaporated in vacuo and the residue was purified by flash chromatography (MPLC, 10-100% EtOAc-hexanes) to give terr-butyl (2-bromopyrimidin- 5-yl)carbamate.LRMS (ESI) calc’d for C9H13BrN302_[M+H]+: 274, Found: 274

According to the analysis of related databases, 56621-91-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; YOUNG, Jonathan; CZAKO, Barbara; ALTMAN, Michael; GUERIN, David; MARTINEZ, Michelle; RIVKIN, Alexey; WILSON, Kevin; LIPFORD, Kathryn; WHITE, Catherine; SURDI, Laura; CHICHETTI, Stephanie; DANIELS, Matthew, H.; AHEARN, Sean, P.; FALCONE, Danielle; OSIMBONI, Ekundayo; WO2011/84402; (2011); 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. 99420-75-4, name is 5-Methylpyrimidine-2-carboxylic acid, the common compound, a new synthetic route is introduced below. COA of Formula: C6H6N2O2

To a solution of 5-methylpyrimidine-2-carboxylic acid (1 g, 7.24 mmol) in DMF (72.4 mL) was added 5-methylpyrimidine-2-carboxylic acid (1 g, 7.24mmol), and N,O- dimethylhydroxylamine hydrochloride (0.777 g, 7.96 mmol). The mixture was cooled to 0oC and 1-propanephosphonic acid cyclic anhydride (50 wt. % solution in EtOAc, 9.21 mL, 14.48 mmol) was added droppwise. The mixture was allowed to warm to RT overnight. LCMS indicated complete conversion to product. The mixture was then diluted with water, extracted with CHCl3:IPA (3:1), and washed with brine and NaHCO3. The mixture was dried over Na2SO4, concentrated in vacuo, and purified by silica gel chromatography (0-100% heptanes:EtOAc) to yield N-methoxy-N,5-dimethylpyrimidine- 2-carboxamide (0.7 g, 3.86 mmol, 53.4 % yield), Example 142.1.1H NMR (500 MHz, CDCl3) delta 8.61 – 8.69 (m, 2 H) 3.61 – 3.79 (m, 3 H) 3.27 – 3.47 (m, 3 H) 2.34 – 2.45 (m, 3 H). LCMS-ESI (pos.) m/z: 182.2 (M+H)+.

The synthetic route of 99420-75-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; 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.; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YANG, Kevin; YEH, Wen-Chen; (700 pag.)WO2018/97945; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 186519-92-6, 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 186519-92-6 as follows.

Svnthesis 8-1 -B; f-Butyl 3-(4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamido)piperidine-1-carboxylate; A solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid (18 mg, 0.09 mmol), HATU (45 mg, 0.12 mmol), and diisopropylethylamine (80 mul_, 0.46 mmol) in DMF (1 mL) was stirred at room temperature for 30 minutes. ferf-Butyl 3-aminopiperidine-1- carboxylate hydrochloride (28 mg, 0.12 mmol) in DMF (0.5 mL) was added and the resulting solution was stirred for 16 hours. The mixture was diluted with brine and extracted with ethyl acetate. The combined organic layers were washed sequentially with NaHCO3 solution, citric acid, and brine, then dried (Na2SO4), filtered, and concentrated. Purification by preparative TLC, eluting with ethyl acetate, gave the title compound as a light yellow oil (10 mg, 29%).1H NMR (500 MHz, CD3OD) delta 1.47 (9H, s), 1.49-1.69 (2H, m), 1.71-1.84 (1 H, m), 2.02- 2.11 (1 H, m), 3.13-3.27 (1 H, m), 3.54-3.68 (1 H, m), 3.86-3.96 (2H, m), 4.00-4.09 (1 H, m), 7.92 (1 H, s), 8.61 (1 H, s); LC-MS Rt 4.29 min; m/z (ESI) 380 [MH+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,186519-92-6, its application will become more common.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; WO2008/75007; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 42839-08-7, 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. 42839-08-7, name is Ethyl pyrimidine-2-carboxylate. A new synthetic method of this compound is introduced below.

The 2 – (2 – methoxy phenoxy) malonamide (II) (35.0 g, 156.1 mmol) dissolved in ethanol (600 ml) in, are tertiary butanol sodium (30.0 g, 312.2 mmol) and 2 – pyrimidine formic acid ethyl ester (III) (23.8 g, 156.1 mmol), stirred under the protection of nitrogen reflux 1 h, TLC detection reaction is completed. Recovering the ethanol, the residue with water (200 ml) mixed beating, filtering, a little water to wash the filter cake, drying, to obtain compound 5 – (2 – methoxyphenoxy) – 1H – [2, 2′] – bipyridyl – 4, 6 – dione (IV) 40.5 g, yield is 83%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,42839-08-7, Ethyl pyrimidine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai Tianci International Pharmaceutical Co., Ltd.; Li Xinjuanzi; Li Jianzhi; Ma Xilai; Chi Wangzhou; Liu Hai; Hu Xuhua; Zheng Xiaoli; Zhai Zhijun; Li Jianxun; (14 pag.)CN104193687; (2017); B;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 149765-15-1, N-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide, 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, Formula: C11H13ClN4O, blongs to pyrimidines compound. Formula: C11H13ClN4O

A solution of the 2-pivaloylamino-4-chloro-pyrrolo[2,3-d]pyrimidine (21.5 g, 85 mmol) and N-iodosuccinimide (19.12 g, 85 mmol) in DMF (150 mL) was stirred at ambient temperature for 18 hr. The red solution was evaporated to an amber residue which upon trituration with cold water gave a yellow solid. The solid was collected by filtration, the filter cake was washed with cold water and then dried in vacuo to yield 30.5 g (94%) of the title compound. 1 H-NMR (DMSO-d6): delta 12.72 (s,1, N (7)-H); 10.14 (s,1, N(2)-H); 7.78 (d,1, H-6); 1.24 (s, 9, pivaloyl methyls). mp 218-220 C.

The synthetic route of 149765-15-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Isis Pharmaceuticals, Inc.; US6093807; (2000); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia