Tag: M.W:100-200

Electric Literature of 38275-43-3, 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. 38275-43-3, name is 2-(Methylthio)pyrimidine-5-carbonitrile. A new synthetic method of this compound is introduced below.

Reference Example 231 To a mixture of 4- [3- (methoxymethoxy) propyl]-3- (l-methylethyl)-lH-pyrazole (1.00 g), 2-methylthiopyrimidine-5- carbonitrile (0.80 g) and N, N-dimethylformamide (15 ml) was added sodium hydride (60%, in oil, 0.24 g) at0 C, and, after termination of hydrogen generation, the mixture was stirred at room temperature for2 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried(MgS04) and concentrated. A mixture of the obtained residue,conc. hydrochloric acid (3 drops) and methanol (20 ml) was refluxed for 4 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried(MgS04) and concentrated. The residue was subjected to silica gel column chromatography, and2- [4- (3-hydroxypropyl)-3- (l-methylethyl)-lH-pyrazol-1-yl] pyrimidine-5-carbonitrile (450 mg, yield36%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-chloroform (1: 4, volume ratio). melting point:153-154 C. H-NMR (CDC13) 5 : 1.38 (6H, d, J= 7. 0Hz), 1.44 (1H, t, J= 5.2Hz), 1.84-2. 00 (2H, m), 2.62 (2H, t, J= 7.8Hz), 3.10 (1H, septet, J= 7. 0Hz), 3.77 (2H, q, J= 5.9Hz), 8.31 (1H, s), 8.93 (2H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,38275-43-3, 2-(Methylthio)pyrimidine-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA CHEMICAL INDUSTRIES, LTD.; WO2003/99793; (2003); 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. 13877-55-9, name is 7-Hydroxypyrazolo[4,3-d]pyrimidine, the common compound, a new synthetic route is introduced below. HPLC of Formula: C5H4N4O

Compound 28: DMF (1.05 mL) was added to a solution containing 27 (1.0 g, 7.3 mmol) in thionyl chloride (21 mL). Heated the stirring solution to 90 C. for 1 hour. Cooled the homogeneous reaction mixture to room temperature. Concentrated to remove volatiles and diluted the reaction mixture with EtOAc followed by ice. Extracted the aqueous layer with EtOAc. Combined the organics, washed with saturated NaHCO3, dried with MgSO4, filtered and concentrated to afford 28 (0.73 g, 64%), ES (+) MS m/e=155.

The synthetic route of 13877-55-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sunesis Pharmaceuticals, Inc.; US2007/27166; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 108-53-2 ,Some common heterocyclic compound, 108-53-2, molecular formula is C4H5N3O, 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.

REFERENCE EXAMPLE 5 Production of 2-amino-5-bromo-4-hydroxypyrimidine To a solution of isocytosine (1.04 g, 9.36 mmol) in acetic acid (25 ml) are added dropwise bromine (0.51 ml, 9.83 mmol) at room temperature. After the addition is completed, the reaction mixture is stirred for 1 hour at this temperature, successively concentrated under reduced pressure to give the residue, which is washed with ethyl ether, dried to afford white powders(2.49 g, 98%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,108-53-2, its application will become more common.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6194419; (2001); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 923282-39-7 ,Some common heterocyclic compound, 923282-39-7, 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.

To a solution of 2-[3-methoxy-4-[[2-(trifluoromethyl)-4-pyridyl]oxy]phenyl]ethanamine (0.39 g, 1.2 mmol) in acetonitrile (30 mL) was added triethylamine (1.5 g, 4.8 mmol). The solution was stirred for 5 min at room temperature at which time 7-chloro-1-methyl-pyrazolo[4,3-d]pyrimidine (0.25 g, 1.2 mmol) was added. The reaction mixture was stirred at room temperature overnight. Water was added and was extracted with ethyl acetate (3*). The combined organic layers were washed with water, dried over Na2SO4 and concentrated in vacuo. The residue was purified by HPLC to provide 85 mg (0.19 mmol, 17%) of the product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,923282-39-7, its application will become more common.

Reference:
Patent; BASF SE; Grammenos, Wassilios; Craig, Ian Robert; Boudet, Nadege; Mueller, Bernd; Dietz, Jochen; Lauterwasser, Erica May Wilson; Lohmann, Jan Klaas; Montag, Jurith; US2014/371065; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
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. 19858-50-5, name is (2-(Methylthio)pyrimidin-5-yl)methanol, molecular formula is C6H8N2OS, 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. Quality Control of (2-(Methylthio)pyrimidin-5-yl)methanol

To the solution of (2-(methylthio)pyrimidin-5-yl)methanol (0.88 g, 5.6 mmol) in DCM (20 ml) at 0°C was added triphenylphosphine (2.1 g, 7.9 mmol) and carbon tetrabromide(2.6 g, 7.9 mmol). The resulting solution was stirred at 0°C for 1 hour. The reaction mixture was purified on silica gel column using EtOAc/hexane as eluting solvents to give 5- (bromomethyl)-2-(methylthio)pyrimidine. LC/MS: (M+ 1 ): 218.90; 220.90.

With the rapid development of chemical substances, we look forward to future research findings about 19858-50-5.

Reference:
Patent; MERCK SHARP & DOHME CORP.; TANG, Haifeng; YANG, Shu-Wei; MANDAL, Mihir; SU, Jing; LI, Guoqing; PAN, Weidong; TANG, Haiqun; DEJESUS, Reynalda; PAN, Jianping; HAGMANN, William; DING, Fa-Xiang; XIAO, Li; PASTERNAK, Alexander; HUANG, Yuhua; DONG, Shuzhi; YANG, Dexi; WO2015/171474; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 29458-38-6, 6-Methoxypyrimidine-2,4(1H,3H)-dione, 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, 29458-38-6, blongs to pyrimidines compound. Formula: C5H6N2O3

A mixture of 2,4-dihydroxy-6-methoxypyrimidine (15g, 0.106mol) in phosphorus (III) oxychloride (400ml) was heated under reflux for 4 hours to give solution. Excess phosphorus (IQ) oxychloride was removed by evaporation, the residue treated with ice/water and extracted with EtOAc. The combined extracts were washed with water, dried (Na2SO4) . and the solvent removed by evaporation to give 2,4-dichloro-6-methoxypyrimidine (5.5g, 30%) as an oil; NMR Spectrum 3.96 (s, 3H), 6.63 (s, IH); Mass Spectrum 179 [MH]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,29458-38-6, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/109026; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1513-69-5, 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 1513-69-5 as follows.

Example 15: 4-chloro-6-(trifluoromethyl)pyrimidin-2-amine (24)2-Amino-6-(trifluoromethyl)pyrimidin-4-ol (200 mg, 1.1 mmol) is dissolved in POCI3 (3 eq., 0.3 ml_, 3.3 mmol) and dimethylaniline (0.28 ml_, 2 eq.) is added. The reaction mixture is heated at 7O0C for 4 h. The resulting mixture is poured into a mixture of ice-water, and the resulting precipitate is collected to yield the desired compound 24 in 59%. ESI-MS m/z 198 [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,1513-69-5, its application will become more common.

Reference:
Patent; COVALYS BIOSCIENCES AG; WO2006/114409; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 99420-75-4 ,Some common heterocyclic compound, 99420-75-4, molecular formula is C6H6N2O2, 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 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,0- dimethylhydroxylamine 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 RT overnight. LCMS indicated complete conversion to product. The mixture was diluted with water, extracted with CHC13:IPA (3: 1) and washed with brine and NaHC03. The mixture was dried over Na2S04, concentrated in vacuo and purified by silica gel chromatography (0-100% heptane s:EtO Ac) to yield N-methoxy-N,5-dimethylpyrimidine- 2-carboxamide (0.7 g, 3.86 mmol, 53.4 % yield). NMR (500 MHz, CDC13) 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 +.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,99420-75-4, its application will become more common.

Reference:
Patent; AMGEN INC.; CHEN, Yinhong; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; RAMSDEN, Philip Dean; SHARMA, Ankit; (321 pag.)WO2018/93576; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1196152-00-7 ,Some common heterocyclic compound, 1196152-00-7, molecular formula is C7H7ClN2O2, 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-chloropyrimidin-4-yl)-l-methyl-lH-pyrazol-5-amine (9.C). To a solution of acetonitrile (0.19 ml, 3.60 mmol) in THF 4.0 ml was slowly added butyllithium (1.5 ml, 2.5M solution in hexanes, 3.77 mmol) at -78 0C and the mixture was stirred at -78 0C for 50 min. Ethyl 2-chloropyrimidine-4-carboxylate, 9.B (0.64 g, 3.43 mmol) in THF (3.0 ml) was added dropwise at -78 0C. The reaction mixture was continued to stirre at -78 0C for Ih. The reaction mixture was allowed to warm up to room temperature and stirred for 1 h. The reaction was quenched by addition of water (15.0 ml). The aquouse layer was acidified to pH = 5 with IN HCl, and extracted with ethyl acetate (30 x 3 ml). The combined organic layer was washed with brine (20 ml) and dried over Na2SO4. The solvent was removed to give the intermediate ketonitrile as a dark brown solid. The crude ketonitrile was treated with methyl hydrazine (0.37 ml, 6.86 mmol) in methanol (6.0 ml) and 2N HCl (3.0 ml) at 80 0C for 6 h. LC-MS results indicated the product was formed. The crude mixture was purified by preperative HPLC to give 9.C. 0.23g, yield 32%. MS ESI (pos.) m/e: 209.9 (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,1196152-00-7, its application will become more common.

Reference:
Patent; AMGEN INC.; DU, Xiaohui; FU, Zice; HOUZE, Jonathan, B.; JIAO, Xianyun; KIM, Yong-jae; LI, Leping; LIU, Jinqian; LIZARZABURU, Mike; MEDINA, Julio; SHEN, Wang; TURCOTTE, Simon; YU, Ming; WO2010/93849; (2010); A2;,
Pyrimidine | C4H4N2 – PubChem,
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. 64951-06-0, name is Ethyl imidazo[1,2-a]pyrimidine-2-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 64951-06-0

To a stirred solution of ethyl imidazo[l ,2-alpha]pyrimidine-2-carboxylate or ethyl imidazo[1,2-a]pyrimidine-3-carboxylate (1 g, 5.2 mmol) in ethanol (40 mL) was added hydrazine monohydrate (0.28 mL, 5.7 mmol). The reaction was heated to 75 C for 16 h and was concentrated under reduced pressure. The resulting light yellow solid was suspended in diethyl ether and filtered to collect ethyl 2-amino-1H-imidazole-4- carboxylate (800 mg, 100%) as a white solid. [00243] 1E NMR (400 MHz, CD3OD) 5 7.27 (s, 1H), 4.24 (q, J= 7.0 Hz, 2H), 1.31(t, J= 7.0 Hz, 3H).[00244] 13C NMR (500 MHz, CD3OD) delta 165.5, 156.1, 131.8, 125.7, 63.8, 17.3.[00245] HPLC Phenomenex LUNA C- 18 4.6 x 50 mm, 0 to 100% B over 4 minutes, 1 minutes hold time, A = 90% water, 10% methanol, 0.1% TFA, B = 10% water, 90% methanol, 0.1% TFA, RT = 0.46 min, 100% homogeneity index.[00246] Anal. Calcd for C6H9N3O2: C, 46.44; H, 5.84; N5 27.08. Found: C, 46.17;H, 5.65; N, 27.28.[00247] HRMS: Anal. Calcd. for C6Hi0N3O2 156.0773 found: 156.0779 (M+H)+.

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, 64951-06-0, Ethyl imidazo[1,2-a]pyrimidine-2-carboxylate.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2006/71752; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia