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 55405-67-9, name is 3-Bromopyrazolo[1,5-a]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 55405-67-9

Weigh into a round bottom flask 3-bromopyrazolo [1, 5-a] pyrimidine (Lynch et al. Can. J. Chem. 1975, 53, 119-122; 0.095 g, 0.48 mmol), 2- (pyridin-2-yl)-5, 6-dihydro- 4H-pyrrolo [1, 2-b] pyrazole-3-boronic acid (Preparation 5; 0.10 g, 0.44 MMOL), triphenylphosphine (Aldrich; 0.007 g, 0.027 mmol) and tris (dibenzylideneacetone) dipalladium (0) (Aldrich; 0.015 g, 0.016 mmol). Add p-dioxane (6 ml) and 2. 0M aqueous potassium carbonate (2 mL). Stir and reflux under nitrogen for 6 h. Dilute with ethyl acetate, separate the organic layer, concentrate under reduced pressure, and chromatograph on flash silica using neat acetonitrile. Purify on a preparative reverse phase C-18 high-performance chromatography column using a gradient from 5% to 100% acetonitrile in 0.03% aqueous hydrochloric acid. Concentrate the pure fractions under reduced pressure, dissolve the residue in distilled water, and make basic by adding 1. OM aqueous sodium hydroxide. Extract with dichloromethane, dry the organic layer over anhydrous sodium sulfate, filter, and concentrate under reduced pressure to obtain 6 mg (4.5%) of the title compound as a yellow solid. TOF MS ES+ exact mass calculated for C17HL5N6 (MA : m/z = 303.1358 ; Found: 303. 1371.’H NMR (400 MHz, CDCL3) 8 8.66 (d, J = 2 Hz, 1H), 8. 64 (d, J = 2 Hz, 1H), 8.41 (dd, J = 4,2 Hz, 1H), 8.31 (s, 1H), 7.70 (M, 2H), 7.21 (M, 1H), 6.79 (dd, J = 7,4 Hz, 1H), 4.30 (t, J = 7 Hz, 2H), 3.10 (t, J = 8 Hz, 2H), 2.68 (M, 2H).

With the rapid development of chemical substances, we look forward to future research findings about 55405-67-9.

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/50659; (2004); A1;,
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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 43024-61-9, name is Ethyl 7-hydroxypyrazolo[1,5-a]pyrimidine-6-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of Ethyl 7-hydroxypyrazolo[1,5-a]pyrimidine-6-carboxylate

Stage 1.2: 7-Chloro-pyrazolo[1,5-a]pyrimidine-6-carboxylic acid ethyl ester Literature reference:. 7-Hydroxy-pyrazolo[1,5-a]pyrimidine-6-carboxylic acid ethyl ester (8.98 g; 43.3 mMol) (Example 1; stage 1.1) is suspended in POCI3 (100 mL) followed by addition of N,N-diethylaniline (11.76 mL; 73.2 mMol) at RT. The slightly yellowish suspension is slowly heated to relux (oil bath at 120C) and kept stirring for 2 h. After cooling to RT, most of the POCl3 is removed under reduced pressure. The oily residue is poured into ice water (400 mL), followed by extraction with TBME (3 x 250 mL). The combined organics are washed with NaHCO3 satd. solution (2 x 100 ML) and water, dried (Na2SO4), concentrated under reduced pressure and recrystallized from n-heptane to the title compound 1.2 as yellow crystals (3.65 g); mp. 93-95 C; HPLC: tRet = 4.73 minutes (System1).

With the rapid development of chemical substances, we look forward to future research findings about 43024-61-9.

Reference:
Patent; Novartis AG; EP1918291; (2008); 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. 31462-58-5, name is 5-Iodopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. name: 5-Iodopyrimidine

General procedure: A sealed 10 mL glass tube containing aryl halide (1 mmol), CS2(0.5 mmol) and [DBUH]+[OAc]- (1 mL) was placed in the cavity of a microwave reactor and irradiated for 5-60 min at 100-120 C and power 150 W. After cooling to room temperature, the reaction mixture was extracted with Et2O (3 × 5 mL) and the [DBUH]+[OAc]-was separated from the product. The organic layers were combined and the solvent removed under reduced pressure to provide the crude product, which was further purified by column chromatography on silica gel using petroleum ether/EtOAc as the eluent. The recovered [DBUH]+[OAc]- was washed with diethyl ether and could be reused in the next reaction. All of the products are known compounds and their characterisation data were compared and are consistent with literature reports.

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, 31462-58-5, 5-Iodopyrimidine.

Reference:
Article; Zhou, Yongsheng; Journal of Chemical Research; vol. 40; 5; (2016); p. 305 – 307;,
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Adding a certain compound to certain chemical reactions, such as: 17326-27-1, 2-Chloro-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde, 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: C10H7ClN2O2, blongs to pyrimidines compound. Formula: C10H7ClN2O2

To a stirred solution of G2 (1.0 mmol) in THF (2.0 mL) was added Et3N (2.0 mmol). The mixture was cooled to 0 C. After 5 min, an amine (1.0 mmol) was added dropwise and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with CH2Cl2 (10 mL) and washed with brine (10 mL). The organic layer was dried over anhydrous MgSO4 and concentrated in vacuo. The crude product was purified by flash column chromatography to give G3. 1H NMR (400 MHz, CDCl3) delta 2.44 (s, 3H), 6.89 (t, J=6.8 Hz, 1H), 7.11 (t, J=7.2 Hz, 1H), 7.34 (t, J=7.6 Hz, 2H), 7.62 (d, J=6.4 Hz, 1H), 7.76 (d, J=8.0 Hz, 2H), 8.80 (d, J=6.8 Hz, 1H), 10.27 (s, 1H), 11.67 (brs, 1H); 13C NMR (100 MHz, CDCl3) delta 18.1, 94.6, 113.6, 121.8, 124.2, 125.9, 128.7, 133.6, 138.1, 138.9, 152.5, 153.8, 160.2, 190.2.

The synthetic route of 17326-27-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Brodin, Priscille; Christophe, Thierry; No, Zaesung; Kim, Jaeseung; Genovesio, Auguste; Fenistein, Denis Philippe Cedric; Jeon, Heekyoung; Ewann, Fanny Anne; Kang, Sunhee; Lee, Saeyeon; Seo, Min Jung; Park, Eunjung; Contreras Dominguez, Monica; Nam, Ji Youn; Kim, Eun Hye; US2011/178077; (2011); A1;,
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Electric Literature of 634468-96-5, 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.634468-96-5, name is tert-Butyl 4-(pyrimidin-5-yl)piperazine-1-carboxylate, molecular formula is C13H20N4O2, molecular weight is 264.3235, as common compound, the synthetic route is as follows.

A mixture of 3.5 g of the compound obtained in the preceding step in 20 ml of dioxane is admixed at AT with 50 ml of a 2N solution of HCl in ether, which is left with stirring at AT for 1 hour and concentrated under vacuum. This gives a yellow solid which is used as it is.

Statistics shows that 634468-96-5 is playing an increasingly important role. we look forward to future research findings about tert-Butyl 4-(pyrimidin-5-yl)piperazine-1-carboxylate.

Reference:
Patent; sanofi-aventis; US2005/176722; (2005); A1;,
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Reference of 14001-69-5 ,Some common heterocyclic compound, 14001-69-5, molecular formula is C5H5N3O3, 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.

Example 40Synthesis of 4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-(2-methoxy-5-pyrimidinyl)-6-(4-morpholinyl)-1,3,5-triazin-2-amineThe compound was synthesized according to Method A.To a solution of sodium methoxide (0.090 g of sodium) in MeOH (12 mL) was added 0.486 g (3.03 mmol) of 2-chloro-5-nitropyrimidine, and the mixture was heated under reflux for 1 hr. After cooling, the mixture was concentrated in vacuo, extracted with EtOAc, and washed with water. The aqueous layer was extracted with CHCl3 and the combined organic layers were dried (Na2SO4), and concentrated, to give 0.347 g (75% yield) of 2-methoxy-5-nitropyrimidine as a yellow powder: 1H NMR (CDCl3) delta9.31 (s, 2H), 4.17 (s, 3H); LCMS (APCI+) m/z: 156 (MH+, 100%).To 0.342 g (2.20 mmol) of the above nitro compound in MeOH (20 mL) was added 0.30 g of 10% Pd/C and the mixture was stirred under hydrogen (25 in/Hg) for 18 hrs. The reaction mixture was filtered through celite, and concentrated, to give 0.274 g (100% yield) of 5-amino-2-methoxypyrimidine as a colorless oil: 1H NMR (DMSO-d6) delta 8.05 (s, 2H), 3.94 (s, 3H); LCMS (APCI+) m/z: 126 (MH+, 100%).To 0.274 g (2.19 mmol) of the above amino compound in THF (3 mL) was added 1.25 mL of NaHMDS (2 M solution in THF) and the mixture was stirred for 10 min. A solution of 0.31 g (0.78 mmol) of 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazole in THF (5 mL) was added and the resulting mixture was stirred for 90 min. The reaction mixture was neutralized with acetic acid, diluted with water, and extracted with EtOAc. The organic layer was washed with water and aq. NH3, dried, and concentrated. Recrystallization from EtOH/CH2Cl2 gave 0.098 g (26% yield) of 4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-(2-methoxy-5-pyrimidinyl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine: mp 255-258 C.; 1H NMR (DMSO-d6) 810.07 (s, 1H), 8.88-8.74 (m, 2H), 8.15-7.42 (m, 3H), 6.97 (d, J=8.0 Hz, 1H), 3.98 (s, 3H), 3.93 (s, 3H), 3.82-3.72 (m, 8H); Anal. Calcd. for C21H21F2N6O3: C, 52.0; H, 4.4; N, 26.0. Found: C, 52.1; H, 4.5; N, 26.0%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14001-69-5, its application will become more common.

Reference:
Patent; Pathway Therapeutics Limited; US2011/9405; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
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. 6960-17-4, name is 2,5-Dimethoxypyrimidin-4-amine. A new synthetic method of this compound is introduced below., name: 2,5-Dimethoxypyrimidin-4-amine

Example 4 Preparation of 2-amino-5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine (Ia) To a 700 mL jacketed vessel equipped with a mechanical stirrer, a dual pH/temperature probe, a nitrogen inlet, and a reflux condenser was added sequentially 27.9 g (0.180 mol) of 4-amino-2,5-dimethoxypyrimidine followed by 165.4 g (0.207 mol) of 16.4 wt % ethoxy carbonylisothiocyanate solution in toluene. The reaction mixture was heated to gentle reflux (87 C.) for 7 h at which time liquid chromatographic (LC) analysis indicated ?95% conversion of starting 4-amino-2,5-dimethoxypyrimidine. The reaction mixture was cooled to 27 C. and allowed to stand overnight. The mixture was heated to 40 C. and then 114.2 g (6.34 mol) of deionized water was added to the mixture. After heating to reflux (?68 C.). , 14.3 g (0.217 mol) of a 50 wt % aqueous hydroxylamine solution was continuously added over a 2 h 15 min period via a peristaltic pump. During the course of the amine addition, the reaction pH rose from 4.44 to 6.95. After complete addition of hydroxylamine, the pump line was flushed with 4.8 g (0.266 mol) of deionized water, the reaction mixture was heated to 81 C., and then stirred an additional 3 h during which time the reaction pH naturally raised to 7.40. The reaction mixture was cooled to ambient temperature (26 C.). The reaction mixture was then suction transferred into a temporary holding vessel. The reactor was washed with two 30 g portions of water. These water washes were combined with the reaction mixture. The combined mixture was suctioned filtered through a coarse Buchner funnel (filtration time about 30 seconds), and the filtrate was collected and filtered a second time through the cake. A final displacement cake wash with ?40 g of methanol was performed and the product was dried at 60 C. under vacuum (?<10 mm Hg; 1333 Pa) to afford 25.37 g of 2-amino-5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine as a light cream colored solid. NMR analysis (using benzyl acetate as an internal standard) indicated an 97.3% purity of 2-amino-5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine active which corresponds to a 70.4% yield. 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, 6960-17-4, 2,5-Dimethoxypyrimidin-4-amine. Reference:
Patent; Dow AgroSciences LLC; Bland, Douglas C.; Hamilton, Christopher T.; US2014/81024; (2014); A1;,
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Reference of 675-11-6, 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. 675-11-6, name is 4,6-Difluoropyrimidin-2-amine, molecular formula is C4H3F2N3, 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.

In a sealable tube, a solution of 4,6-difluoropyrimidin-2-amine (1.0 g, 7.6 mmol) in 1,4-dioxane/dimethylformamide (20.0 mL, 1:1), potassium carbonate (1.6 g, 11.9 mmol) and tert-butylamine (1.7 g, 23.0 mmol) were added. The resulting reaction mixture was stirred at room temperature for 48 h. After completion, the reaction mixture was concentrated under reduced pressure. The crude material was diluted with cold water (10.0 mL) whereupon a solid formed. The solid was filtered and air dried to afford the title compound S7-2 (1.2 g, 85%) as an off-white solid. MS m/z (M+H): 185.1

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 675-11-6, 4,6-Difluoropyrimidin-2-amine.

Reference:
Patent; Celgene Avilomics Research, Inc.; Alexander, Matthew David; Chuaqui, Claudio; Malona, John; McDonald, Joseph John; Ni, Yike; Niu, Deqiang; Petter, Russell C.; Singh, Juswinder; (164 pag.)US2016/75720; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 99420-75-4, 5-Methylpyrimidine-2-carboxylic acid, 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, Product Details of 99420-75-4, blongs to pyrimidines compound. Product Details of 99420-75-4

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, 7.24 mmol), N,Odimethyihydroxylamine hydrochloride (0.777 g, 7.96 mmol). The mixture was cooled to 0 C 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 23 C overnight. LCMS indicated complete conversion to product. The mixture was diluted with water, extracted with CHC13:IPA (3:1) and washed with brine, 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 -dimethylpyrimidine2-carboxamide (0.7 g, 3.86 mmol, 53.4 % yield). 1H NMR (500 MHz, CDC13) oe 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)t

At the same time, in my other blogs, there are other synthetic methods of this type of compound,99420-75-4, 5-Methylpyrimidine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; CHEN, Yinhong; CHENG, Alan C.; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; PATTAROPONG, Vatee; SWAMINATH, Gayathri; KREIMAN, Charles; MOEBIUS, David C.; SHARMA, Ankit; (543 pag.)WO2018/93580; (2018); A1;,
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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. 946161-16-6, name is (R)-Methyl 2-((2-chloro-5-nitropyrimidin-4-yl)(isopropyl)amino)butanoate, molecular formula is C12H17ClN4O4, 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. name: (R)-Methyl 2-((2-chloro-5-nitropyrimidin-4-yl)(isopropyl)amino)butanoate

50 g 23 in 375 mL of tetrahydrofurane is hydrogenated in the presence of 5 g Platinum on Carbon (5%) at a hydrogene pressure of 3 bar and at 35 C until no further hydrogene consumed. 2.5 g vanadyl acetylacetonate are added and the hydrogenation is continued. The suspension is filtered to remove the catalysts. The solvent is removed under reduced pressure. 150 mL 2-propanol are added to the residue and heated to reflux. 300 ml of demineralised water are added. The suspension is cooled slowly to 2 C. The suspension is suction filtered and washed with a cold mixture of 2- propanol and demineralised water. After drying in a vacuum drying oven at 50C, 36 g (90% of theory) of product 24 is obtained

With the rapid development of chemical substances, we look forward to future research findings about 946161-16-6.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2007/90844; (2007); A1;,
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