Tag: M.W:100-200

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 6960-17-4 ,Some common heterocyclic compound, 6960-17-4, molecular formula is C6H9N3O2, 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.

In 2000ml four bottles in order to join4-Amino-2,5-dimethoxypyrimidine (116.7 g, 0.75 mol)And toluene (188 g),Heated to 70 ~ 75 ,A solution of phenoxycarbonyl isothiocyanate in toluene was added dropwise,About 1 hour drop finished,Continue to heat 2 hours,The reaction was monitored by HPLC.To room temperature,The filter cake was washed twice with 50 ml of ethanol and dried at 60 C to give the desired intermediate4- [4- (2,5-dimethoxypyrimidinyl)] – 3-ThioureaPhenyl ester234.9g, the content is 98.1%, the yield is up to 92.0%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6960-17-4, its application will become more common.

Reference:
Patent; Beijing Yingli Refinement Technology Development Co., Ltd; Hubei Huida Technology Development Co., Ltd; Ling, Yun; Yan, Wei; Huang, Bibo; (7 pag.)CN105294697; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 695-87-4, Adding some certain compound to certain chemical reactions, such as: 695-87-4, name is 5-Methoxypyrimidin-4(1H)-one,molecular formula is C5H6N2O2, 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 695-87-4.

EXAMPLE 4 4-Chloro-5-methoxypyrimidine (VII) Materials: Procedure: To a stirred slurry of 4-hydroxy-5-methoxypyrimidine in toluene (171 mL) was added DIPEA and POCl3 at room temperature under nitrogen atmosphere, The reaction mixture was stirred for about 1-2 hours at 60 to 70 C. under nitrogen atmosphere to complete the reaction. The reaction was quenched by adding 90 mL of 1.55N NaOH at 5 to 8 C. and the aqueous phase was separated. The organic layer was washed with saturated NaHCO3 solution (31 mL) and polish filtered. Concentration of the intermediate was determined by HPLC quantitation. This 0.37 to 0.43M solution of chloromethoxypyrimidine was used without further purification,

According to the analysis of related databases, 695-87-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; US5550239; (1996); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 4472-44-0, 2-Chloro-4,6-dimethylpyrimidine, 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 C6H7ClN2, blongs to pyrimidines compound. Computed Properties of C6H7ClN2

[0586] Synthesis of methyl 4, 6-dimethylpyrimidine-2-carboxylate: [0587] To a stirred solution of 2-chloro-4, 6-dimethylpyrimidine (1 g, 7.05 mmol) in MeOH: CH3CN (4: 1, 20 mL) under argon atmosphere were added triethyl amine (1.98 mL, 14.02 mmol) and Pd(dppf)2Cl2 (1 g, 1.40 mmol) at room temperature; heated to 100 C and stirred for 20 h under CO pressure in steel bomb. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was filtered through celite and the filtrate was concentrated in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 30% EtOAc/ Hexanes to afford methyl 4,6-dimethylpyrimidine-2-carboxylate (400 mg, 34%) as an off- white solid. [0588] 1H-NMR (CDCI3, 400 MHz): delta 7.20 (s, 1H), 4.07 (s, 3H), 2.61 (s, 6H); LC-MS: 87.29%; 167.2 (M++l); (column: X-Bridge C-18, 50 3.0 mm, 3.5 mupiiota); RT 1.47 min. 0.05% Aq TFA: ACN; 0.8 mL/min); TLC: 30% EtOAc/ Hexanes (R 0.3).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4472-44-0, 2-Chloro-4,6-dimethylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew, J.; BURSAVICH, Matthew, Gregory; WO2013/142269; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 101257-82-3, 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. 101257-82-3, name is 4-Amino-5-chloropyrimidine, molecular formula is C4H4ClN3, 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.

L. [4-(3-Chloropropylsulfanyl)-3-methylpyridin-2-ylmethyl]-(5-chloropyrimidin-4-yl)amine A solution of 2.7 g (20.85 mmol) of 4-amino-5-chloropyrimidine in 20 ml of dimethylformamide is added dropwise to a suspension of 0.75 g (18.25 mmol) of sodium hydride (60% strength in paraffin) in 5 ml of dimethylformamide. The mixture is stirred at room temperature for 20 minutes. A solution of 5 g (17.38 mmol) of 2-chloromethyl-4-(3-chloropropylsulfanyl)-3-methylpyridine in 5 ml of dimethylformamide is then added dropwise in the course of 30 minutes and the mixture is then stirred at room temperature for 4 hours. It is concentrated in a high vacuum and the residue is taken up in 150 ml of water and 100 ml of dichloromethane with vigorous stirring. The aqueous phase is extracted with 3*50 ml of dichloromethane. The organic extracts are dried over magnesium sulfate and concentrated. The residue is purified by chromatography on silica gel (eluent: toluene/ethyl acetate/methanol/conc. ammonia=6/3.5/0.5/0.05). The elude is concentrated and the residue is then digested with diethyl ether. After filtration and drying of the precipitate, 2.8 g (47%) of the title compound are obtained as a colorless solid, which is used without further purification.

According to the analysis of related databases, 101257-82-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BYK Gulden Lomberg Chemische Fabrik GmbH; US6395732; (2002); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 60025-06-1, 1-(4,6-Dichloropyrimidin-5-yl)ethanone, 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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

Synthesis of Compound 6.1. Hydrazine hydrate (107 uL, 2.20 mmol) was slowly added to a solution of 1-(4,6-dichloro-pyrimidin-5-yl)-ethanone (Clark, J. et al J. Chem. Soc. 1976, 9, 1004) (400 mg, 2.09 mmol) and triethylamine (280 uL, 2.0 mmol) in 1,4-dioxane (7 mL) at 8 C. After the addition was complete, the reaction mixture was warmed to RT. After 2.5 hr, the reaction mixture was filtered through celite and then evaporated to afford compound 6.1 (200 mg) as a yellow solid. 1H-NMR (400.13 MHz, DMSO-d6) 14.07 (s, 1H), 8.75 (s, 1H), 2.64 (s, 3H). MS m/z 169 [M+1]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60025-06-1, 1-(4,6-Dichloropyrimidin-5-yl)ethanone, and friends who are interested can also refer to it.

Reference:
Patent; Sunesis Pharmaceuticals, Inc; US2009/5359; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 108-53-2, 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.108-53-2, name is 2-Aminopyrimidin-4(1H)-one, molecular formula is C4H5N3O, molecular weight is 111.102, as common compound, the synthetic route is as follows.

In a three neck IL round bottom flask equipped with reflux condenser was added 2-amino- 4(3H)-pyrimidinone A.ll (10Og, 0.9 mol) (available from Toronto Research Chemicals) followed by POCl3 (168 ml, 1.800mol) at room temperature and under an atmosphere of N2. To this was cautiously added ClSO3H (4.8ml, 72.01 mmol). The solution was heated to 950C for 4 hrs, before it was cooled to room temperature. The solution was then cooled in an ice bath before it was poured into 700ml of ice water with vigorous stirring. Adjusted the pH to ~7 with NH4OH (30% by weight) (temperature was held below 2O0C). A tan colored solid was collected by filtration. The solid was dried under vacuum at 7O0C overnight to afford 4-chloro- 2-pyrimidinamine A.12 (108g, 92%) as an off white solid.1H NMR (400 MHz, (CD)3SO) delta 8.17 (d, J = 5.2 Hz, IH), 7.07 (br s, 2H), 6.64 (d, J = 5.2 Hz, IH); ESI MS: M + H+ 130.0 m/z.

Statistics shows that 108-53-2 is playing an increasingly important role. we look forward to future research findings about 2-Aminopyrimidin-4(1H)-one.

Reference:
Patent; AMGEN INC.; WO2009/158011; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia