Tag: M.W:200-300

Adding a certain compound to certain chemical reactions, such as: 941685-26-3, 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine, 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, Safety of 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine, blongs to pyrimidines compound. Safety of 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

A 100 mL round bottom flask was charged with 4-chloro-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (1.00 g, 3.52 mmol), 1-butanol (25.0 mL), [1-(triisopropylsilyl)-1H-pyrrol-3-yl]boronic acid (1.41 g, 5.28 mmol), water (25.0 mL) and potassium carbonate (1.27 g, 8.8 mmol). This solution was degased 4 times, filling with nitrogen each time. Tetrakis(triphenylphosphine)-palladium(0) (0.41 g, 0.35 mmol) was added and the mixture was degased 4 times, filling with nitrogen each time. The reaction was stirred overnight at 100 C. and cooled to room temperature. The mixture was filtered through a bed of celite and the celite was rinsed with ethyl acetate (42 mL). The filtrate was combined and the organic layer was separated. The aqueous layer was extracted with ethyl acetate. The organic extracts were combined and concentrated under vacuum with a bath temperature of 30-70 C. to give the title compound 4-(1H-pyrrol-3-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine. Yield: 83%; LC-MS: 315.2 (M+H)+.

The synthetic route of 941685-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Huang, Taisheng; Xue, Chu-Biao; Wang, Anlai; Kong, Ling Quan; Ye, Hai Fen; Yao, Wenqing; Rodgers, James D.; Shepard, Stacey; Wang, Haisheng; Shao, Lixin; Li, Hui-Yin; Li, Qun; US2011/224190; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 663194-10-3, Adding some certain compound to certain chemical reactions, such as: 663194-10-3, name is 4-(4-Bromopyrimidin-2-yl)morpholine,molecular formula is C8H10BrN3O, 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 663194-10-3.

In Nu,Nu-dimethylformamide (DMF) (537 mu) was dissolved 4- (difluoromethyl)-N-(4-fluoro-5-(tributylstannyl)-2-((3S,5R)-3,4,5-trimethylpiperazin- l-yl)phenyl)-6-(2-(trimethylsilyl)ethoxy Nicotinamide (107 mg, 0.134 mmol). To the solution was added 4-(4-bromopyrimidin-2-yl)morpholine (36.0 mg, 0.148 mmol), lithium chloride (17.06 mg, 0.402 mmol) and bis(triphenylphosphine)palladium(II) dichloride (5.18 mg, 7.38 muetaiotaomicron) at room temperature and then it was microwaved at the temperature of 120 °C for 3 hours. To the reaction mixture was added water and then extracted with dichloromethane. The organic layer was separated, concentrated and purified by column chromatography on silica gel (0-100percent, 89percent CH2C12, 10percent MeOH, 1percent NH4Ac/CH2Cl2) to afford the title compound. LCMS [M+l]+ = 672.43.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 663194-10-3, 4-(4-Bromopyrimidin-2-yl)morpholine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; ZEPEDA-VELAZQUEZ, Carlos Armando; PODA, Gennady; ISAAC, Methvin; UEHLING, David; WILSON, Brian; JOSEPH, Babu; LIU, Yong; SUBRAMANIAN, Pandiaraju; MAMAI, Ahmed; PRAKESCH, Michael; STILLE, Julia Kathleen; (1053 pag.)WO2017/147700; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 7400-06-8, 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. 7400-06-8, name is 6-Amino-5-(2,2-diethoxyethyl)pyrimidin-4-ol, molecular formula is C10H17N3O3, 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.

7H-Pyrrolo[2,3-d]pyrimidin-4-ol (7).; Formamidine acetate (5, 1.04 Kg,10 mol, 1.25 equiv) was added to 7.52 L of (21percent wt) sodium ethoxide (EtONa) in ethanol (EtOH, 62.5 equiv) and the resulting solution was stirred for 60 minutes. 2-cyano-4,4-diethoxy-butyric acid ethyl ester (4, 1.8 Kg, 8.0 mol) was then added and the resulting reaction mixture was refluxed for seven hours. The stirring was turned off after the solution was cooled and the solids were allowed to settle. The supernatant ethanol solution was removed, leaving the solids in the bottom of the reaction flask. The ethanol was evaporated and the residue was added back to the solids remaining in the reaction flask with water and ice at a ratio of 600 mL/mol. A solution of 6 N aqueous HCl was added to the resulting solution at a ratio of 500 mL/mol at 15° C. The resulting solution was then heated at 45° C. for 45 minutes. The solution was again cooled to 15° C. and the pH was adjusted to 8.0 with the addition of aqueous ammonium hydroxide. The precipitated solids were collected by filtration, washed with water (2.x.225 mL/mol) and pulled dry. The solids were further washed with 1:1 ethyl acetate/heptane (500 mL/mol), then heptane (2.x.250 mL/mol) and dried in vacuum to afford 7H-pyrrolo[2,3-d]pyrimidin-4-ol (7, 738.6g, 1081 g theoretical, 68.3percent) as yellow to brown to yellow crystalline material. For 7: 1H NMR (DMSO-d6, 300 MHz) delta ppm 11.88 (bs, 1H), 11.80 (bs, 1H), 7.81 (s,1H), 7.02 (dd,1H, J=3.2, 2.3 Hz), 6.42 (dd, 1H, J=3.5, 2.3 Hz); C6H5N3O (MW, 135.12), LCMS (EI) m/e 136 (M++H) and (M++Na) m/e 158.

According to the analysis of related databases, 7400-06-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhou, Jiacheng; Liu, Pingli; Lin, Qiyan; Metcalf, Brian W.; Meloni, David; Pan, Yongchun; Xia, Michael; Li, Mei; Yue, Tai-Yuen; Rodgers, James D.; Wang, Haisheng; US2010/190981; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 876343-10-1 ,Some common heterocyclic compound, 876343-10-1, molecular formula is C6H3ClIN3, 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.

4-(4-(5-Fluoro-3-r4-(1-fluoro-cvclopropyl)-benzoylaminol-2-methyl-phenyl)-7H- Pyrrolor2 -dlpyrimidin-6-yl)-3,6-dihvdro-2H-pyridine-1-carboxylic acid dimethylamide(1 ) 4-(4-Chloro-7H-pyrrolor2,3-dlpyrimidin-6-yl)-3,6-dihvdro-2H-pyridine-1-carboxylic acid tert-butyl ester, Intermediate 1To a mixture of 4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine (2.6 g, 9.30 mmol) and dichlorobis(triphenylphosphine)palladium (II) (0.52 g, 0.74 mmol) in 1-propanol (120 ml) and aqueous sodium carbonate solution (2M, 10.23 ml, 20.46 mmol), 4-(4, 4,5,5- tetramethyl-[1 ,2,3]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (3.02 g, 9.77 mmol) was added. The mixture was heated to 100C for 18 hours. After cooling the brownish mixture was diluted with 200 ml water and extracted with DCM. The organic layer was washed with brine (2x) and dried over sodium sulfate, than filtered and evaporated. The residue was purified by flash chromatography on silica (cyclohexane/EtOAc 1 :1 ) to afford the compound Intermediate 1 as a beige solid.MS (ESI): 335 [M+H]+ , 1H-NMR (DMSO-d6): delta (ppm) 12.64 (br s, 1 H), 8.56 (s, 1 H), 6.59 (s, 2H), 4.08 (br s, 2H), 3.57 (m, 2H), 2.55 (m, 2H), 1.45 (s, 9H). (2) 4-Chloro-6-(1.2.3.6-tetrahvdro-pyridin-4-vn-7H-pyrrolor2.3-dlpyrimidine.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,876343-10-1, its application will become more common.

Reference:
Patent; NOVARTIS AG; HENG, Richard; HOEGENAUER, Elizabeth, Kate; KOCH, Guido; PULZ, Robert, Alexander; VULPETTI, Anna; WAELCHLI, Rudolf; WO2013/8095; (2013); 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. 89581-38-4, name is Methyl 5-bromopyrimidine-2-carboxylate, molecular formula is C6H5BrN2O2, 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. Safety of Methyl 5-bromopyrimidine-2-carboxylate

5-(3-((2-((2,4-dichloro-3-(((2-methoxy-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)phenyl)(methyl)amino)-2-oxoethyl)amino)-3-oxopropyl)-N-methyl-1,4,5,6-tetrahydropyrimidine-2-carboxamide (41) To a solution of 5-bromopyrimidine-2-carboxylic acid methyl ester (5.0 g, 23.0 mmol) in THF (10 mL) was added 8 N solution of methyl amine in ethanol (11.5 mL). The reaction mixture was heated 20 min in a microwave oven, cooled down to room temperature and concentrated under pressure to give 5 g of 5-bromo-N-methylpyrimidine-2-carboxamide as a solid LCMS: 216, 218 (M+1).

With the rapid development of chemical substances, we look forward to future research findings about 89581-38-4.

Reference:
Patent; ASTELLAS PHARMA INC.; ALCON RESEARCH, LTD.; US2012/46285; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 955368-90-8, 2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one, 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, Safety of 2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one, blongs to pyrimidines compound. Safety of 2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one

I1 (182.89 mg, 822.85 mumol) and 57-1 (200 mg, 822.85 mumol) were added into 1,4-dioxane (5.00 mL), followed by adding cuprous iodide (156.71 mg, 822.85 mumol), potassium carbonate (159.22 mg, 1.15 mmol) and N,N’-dimethylethylenediamine (79.79 mg, 905.14 mumol, 98.87 muL), the temperature was raised to 95C under nitrogen atmosphere, then reacted for 16 h. Ammonia (20 mL) was added into the reacted mixture, then extracted by EA (3×10 mL), the organic phase was washed by saturated brine (20 mL), dried over anhydrous sodium sulfate, the filtrate was concentrated to give the crude product, which was separated by an automatic column machine COMBI-FLASH (PE/EA=10/1-1/1) to give 57-2. MS m/z: 384.41 [M+H]+

The synthetic route of 955368-90-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shijiazhuang Sagacity New Drug Development Co., Ltd.; QIAN, Wenyuan; YANG, Chundao; LI, Zhengwei; LI, Jie; LI, Jian; CHEN, Shuhui; (137 pag.)EP3572413; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 13162-26-0, 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. 13162-26-0, name is 2,4-Dichloro-6-methyl-5-nitropyrimidine. A new synthetic method of this compound is introduced below.

Isopropylamine(4.5ml) and N,N-diisopropylethylamine(13.2ml) were dissolved into 150ml dichloromethane. The mixture was added dropwise to a solution of 2,4-dichloro-5-nitro-6-methylpyrimidine(10.7g) in dichloromethane(30ml) at 0C. After the completion of the dropwise addition, the mixture was kept at the same temperature to react for half an hour. Purification was conducted by a column chromatography to obtain a bright-yellow solid(10.2g) in a yield of 86.8%. 1H NMR(400 MHz, CDCl3): delta 8.01(s, 1H), 4.48(m, J=4.1, 1H), 2.72(s, 3H), 1.32(d, J=6.8Hz, 6H)ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13162-26-0, 2,4-Dichloro-6-methyl-5-nitropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Si Chuan University; CSPC Zhongqi Pharmaceutical Technology (Shijiazhuang) Co., Ltd.; YANG, Shengyong; WEI, Yuquan; EP2578584; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1224944-77-7, 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.1224944-77-7, name is Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate, molecular formula is C9H8ClN3O2, molecular weight is 225.63, as common compound, the synthetic route is as follows.

Chiral amine ((S) -2- (2-((R) -1-aminoethyl) -4-fluorophenoxy) propyl-3,3,3-d3) carbamic acid tert-butyl ester (10g ) And 5-chloropyrazolo [1,5-a] pyrimidine-3-carboxylic acid ethyl ester (10g)Diisopropylethylamine base (6.5g) in n-butanol solvent (50mL)The target compound was obtained by condensation at 114-120 C for 8 hours.

Statistics shows that 1224944-77-7 is playing an increasingly important role. we look forward to future research findings about Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate.

Reference:
Patent; Jiao Yuqi; (29 pag.)CN110577549; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 13479-88-4, 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. 13479-88-4, name is 5,7-Dichlorothiazolo[5,4-d]pyrimidine, molecular formula is C5HCl2N3S, 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.

Step 5N-(3-(2-Oxa-6-azaspiro[3.3]heptan-6-yl)phenyl)-5-chlorothiazolo[5,4-d]pyrimidin-7-amine Procedure:A mixture of 5,7-dichlorothiazolo[5,4-d]pyrimidine (108 mg, 0.526 mmol), 3-(2-oxa-6-azaspiro[3.3]heptan-6-yl)aniline (100 mg, 0.526 mmol) and DIEA (102 mg, 0.789 mmol) in 5 mL of DMSO was stirred at room temperature for 16 hours. The mixture was poured into water and the precipitate was filtered. The crude N-(3-(2-oxa-6-azaspiro[3.3]heptan-6-yl)phenyl)-5-chlorothiazolo[5,4-d]pyrimidin-7-amine (160 mg, 85%) was used into the next step without purification. LC-MS: 360 [M+H]+, tR=1.53 min.

According to the analysis of related databases, 13479-88-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hermann, Johannes Cornelius; Lowrie, JR., Lee Edwin; Lucas, Matthew C.; Luk, Kin-Chun Thomas; Padilla, Fernando; Wanner, Jutta; Xie, Wenwei; Zhang, Xiaohu; US2012/252777; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 56686-16-9, 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 56686-16-9, name is 5-Bromo-2,4-dimethoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a stirred anhydrous THF containing 5-bromo-2,4-dimethoxypyrimidine (0.29g, 1.3mmol) was added dropwise a 2.5M n-BuLi/hexane solution (0.6mL, 1.4mmol) at 195K under argon atmosphere. After 30min, 8a (0.52g, 1.3mmol) was added and the reaction mixture was stirred for 2h at this temperature. The reaction was allowed to warm to room temperature and quenched by addition of water. The product was extracted with diethyl ether. Then the combined organic layers were dried over MgSO4, filtered and concentrated. Column chromatography on SiO2 with petroleum ether and ethyl acetate (v/v=6/1) as the eluent afforded 0.35g of 1o as a colorless solid in 52% yield.

According to the analysis of related databases, 56686-16-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Hongliang; Pu, Shouzhi; Liu, Gang; Chen, Bing; Dyes and Pigments; vol. 102; (2014); p. 159 – 168;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia