Category: 591-55-9

Reference of 591-55-9, 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 591-55-9 as follows.

A mixture of tert-butyl 2-(tert-butyldimethylsilyloxy)-3-(3-(7- chloro-3-isopropyl- pyrazolo[l,5-a]pyrimidin-5-yl)-5-methoxyphenoxy)-propyl(methyl)- carbamate (600 mg, 0.97 mmol); pyrimidin-5-amine (139 mg, 1.46 mmol); Pd2(dba)3 (136 mg, 0.194 mmol); BINAP (121 mg, 0.19 mmol) and NaOt-Bu (286 mg, 2.31 mmol) in 15 mL of dioxane was heated at 100 C under N2 for 14h. After cooling down to room temperature, water (30 mL) was added and the mixture was extracted with EtOAc (30 mL X 3). The organic phase was concentrated and the residue was purified by preparative TLC on silica gel developed with DCM/MeOH = 20: 1 to afford 2-(tert-butyldimethylsilyloxy)-3-(3-(l- isopropyl-4-(pyrimidin-5-ylamino)- lH- pyrazolo[3,4-b]pyridin-6-yl)-5- methoxyphenoxy)propyl (methyl)carbamate (190 mg, 29 % yield) as a pale yellow solid. ESI-LCMS (m/z): 678.3 [M+l]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,591-55-9, its application will become more common.

Reference:
Patent; EPIZYME, INC.; CHESWORTH, Richard; MORADEI, Oscar, Miguel; SHAPIRO, Gideon; DUNCAN, Kenneth, W.; MITCHELL, Lorna, Helen; JIN, Lei; BABINE, Robert, E.; (200 pag.)WO2016/44650; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.591-55-9, name is 5-Aminopyrimidine, molecular formula is C4H5N3, molecular weight is 95.1, as common compound, the synthetic route is as follows.Computed Properties of C4H5N3

General procedure: A solution of Pd(OAc)2 and BINAP in dry toluene was warmed at 45 C for 5 min. The leaving group-containing purine was then added under N2 bubbling; the mixture was kept at 45 C for 10 min. and KOtBu was added. After 10 min, the appropriate nucleophile was added. The mixture was heated at 100 C under N2 until reaction completion (3 h to 2 days depending upon the nucleophile used). After cooling to room temperature,the mixture was filtered through Celite, and concentrated. The residue was dissolved in CH2Cl2 (75 mL) and washed (1 × 10 mL) with water and brine (2 × 10 mL). The organic layer was dried and concentrated under vacuum. The residue was purified by chromatography on silica gel using various amounts of EtOAc/cyclohexane/ethanol as eluants.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,591-55-9, 5-Aminopyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Houz, Sandrine; Hoang, Nha-Thu; Lozach, Olivier; Le Bras, Jacques; Meijer, Laurent; Galons, Herv; Demange, Luc; Molecules; vol. 19; 9; (2014); p. 15237 – 15257;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 591-55-9, 5-Aminopyrimidine, 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, 591-55-9, blongs to pyrimidines compound. Recommanded Product: 591-55-9

A suspension of 5-bromo-2-methylpyrimidine-4-carboxylic acid methyl ester (89.1 mg, 386 muiotaetaomicron,), 5-aminopyrimidine (55.0 mg, 578 muiotaetaomicron) and potassium phosphate tribasic (115 mg, 540 muiotaetaomicron) in toluene (3 mL) was evacuated and flushed with argon. 4,5-Bis(diphenylphosphino)-9,9- dimethylxanthene (Xantphos; 73.6 mg, 127 muiotaetaomicron) and tris(dibenzylideneacetone)-dipalladium(0) chloroform adduct (39.9 mg, 38.6 muiotaetaomicron) were added and the reaction mixture was stirred at 120C for 16 h. The reaction mixture was poured into ethyl acetate (50 mL) and extracted with water. The organic phase was washed brine and the aqueous layers were back-extracted with ethyl acetate. The organic layers were dried and the solvent was removed. The product was obtained after silica gel chromatography using a heptane/ethyl acetate gradient as light yellow solid (55 mg, 58 %).MS: M = 246.2 (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,591-55-9, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLEICHER, Konrad; FLOHR, Alexander; GROEBKE ZBINDEN, Katrin; GRUBER, Felix; KOERNER, Matthias; KUHN, Bernd; PETERS, Jens-Uwe; RODRIGUEZ SARMIENTO, Rosa Maria; WO2011/154327; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 591-55-9, 5-Aminopyrimidine, 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, name: 5-Aminopyrimidine, blongs to pyrimidines compound. name: 5-Aminopyrimidine

Example 11 Preparation of Compound Nos. 7, 7a and 7b To a solution of 1-(4-(3-cyclopropyl-1H-pyrazol-5-ylamino)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)pyrrolidine-2-carboxylic acid (300 mg, 0.847 mmol) in DMF (4 mL) was added pyrimidin-5-amine (201 mg, 2.11 mmol), HATU (386 mg, 1.016 mmol) and DIPEA (0.24 mL, 1.4 mmol). The reaction mixture was allowed to stir at RT for 16 h. The reaction mixture was diluted with water (40 mL) and extracted with EtOAc (2*25 mL). The organic layer was washed with water (8*30 mL) and dried over anhydrous sodium sulfate. Removal of EtOAc under reduced pressure gave a crude product that was purified by reverse phase HPLC to afford 11 mg of 1-(4-(3-cyclopropyl-1H-pyrazol-5-ylamino)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)-N-(pyrimidin-5-yl)pyrrolidine-2-carboxamide as free base. 1H NMR (400 MHz, CD3OD, formate salt) delta (ppm): 0.58-0.67 (m, 2H), 0.80-0.94 (m, 2H), 1.70-1.78 (m, 1H), 2.09-2.21 (m, 4H), 2.22-2.42 (m, 2H), 2.78-2.81 (m, 2H), 2.82-2.95 (m, 2H), 3.60-2.70 (m, 1H), 3.78-3.88 (m, 1H), 4.78 (dd, 1H), 6.08 (s, 1H), 8.84 (s, 1H), 8.89 (s, 2H). Separation by chiral HPLC provided enantiomers 7a and 7b.

The synthetic route of 591-55-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; CHAKRAVARTY, Sarvajit; RAI, Roopa; GREEN, Michael John; US2014/179668; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 591-55-9, Adding some certain compound to certain chemical reactions, such as: 591-55-9, name is 5-Aminopyrimidine,molecular formula is C4H5N3, 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 591-55-9.

To a solution of 2-isocyano-2-methylpropane (2.033 mL, 17.98 mmol), S-phenyl benzenesulfonothioate (1800 mg, 7.19 mmol) and pyrimidin-5-amine (1026 mg, 10.79 mmol) in 2-methyltetrahydrofuran (2-MeTHF) (10 mL), copper(I) iodide (137 mg, 0.719 mmol) was added. The reaction mixture was stirred at 75C for 16 hrs. The reaction mixture was filtered through silica and the solvent was evaporated and the product purified by silica gel chromatography with hexane and ethyl acetate to obtain the title compound phenyl N-(tert- butyl)-N’-(pyrimidin-5-yl)carbamimidothioate (1.98 g, 6.91 mmol, 96 % yield). LC-MS m/z 287.2(M+H)+, 1.06 min (ret. Time).

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. 591-55-9, 5-Aminopyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CALLAHAN, James Francis; COLANDREA, Vincent J.; COOPER, Anthony William James; GOODWIN, Nicole Cathleen; HUFF, Chelsea Ariane; KARPIAK, Joel; KERNS, Jeffrey K.; NIE, Hong; (404 pag.)WO2018/109647; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 591-55-9, 5-Aminopyrimidine, 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: 5-Aminopyrimidine, blongs to pyrimidines compound. Recommanded Product: 5-Aminopyrimidine

To a solution of pyrimidin-5-amine (565 mg, 5.94 mmol) and diisopropylethylamine (1.046 g, 8.09 mmol) in dichloromethane (12 mL), was added a solution of ditrichloromethyl carbonate (601 mg, 2.03 mmol) in dichloromethane (6 mL). The resulting mixture was stirred at room temperature for 15 min, and 32-3 (500 mg, 1.49 mmol) and triethylamine (902 mg, 8.91 mmol, 6.00 equiv) were added sequencially. The reaction mixture was stirred at room temperature for 5 h and then the reaction was quenched by addition of methanol and then water. The reaction was extracted with dichloromethane, washed with water and brine, and dried over anhydrous sodium sulfate. After concentration, the residue was purified by silica gel column with ethyl acetate/petroleum ether (1/5) as the eluent to afford the desired product (570 mg, 84% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,591-55-9, 5-Aminopyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; INVENTISBIO INC.; DAI, Xing; WANG, Yaolin; (187 pag.)WO2017/139414; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 591-55-9, 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. 591-55-9, name is 5-Aminopyrimidine, molecular formula is C4H5N3, 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.

A solution of X-Phos (0.04 equiv) and Pd2(dba)3 (0.02 equiv) in toluene (15 vol) was bubbled with nitrogen and heated to 60 C for 15 min. (2S,4R)-1-(2-(3-acetyl-5-bromo-1H-indol-1-yl)acetyl)-4-fluoro-N-(4-phenylbutyl)pyrrolidine-2-carboxamide (1 equiv), 5- aniinopyriniidine (1.2 equiv) and sodium tert-butoxide (1.4 equiv) was added to the reaction mixture and the reaction mixture was heated to 100 C for 16 h. After completion of the reaction, the reaction mixture was quenched with water. The resulting mixture was extracted with ethyl acetate. The organic layer was separated, dried over anhydrous Na2S04, filtered and then concentrated. The residue was purified by column chromatography on silica gel using DCM/MeOH to give (2S,4R)-1-(2-(3-acetyl-5-(pyrimidin-5-ylamino)-1H-indol-1-yl)acetyl)-4-fluoro-N-(4-phenylbutyl)pyrrolidine-2-carboxamide. H NMR (400 MHz, DMSO-d6) delta 8.57 (s, 1H), 8.48 – 8.45 (m, 3H), 8.22 (s, 1H), 8.02 – 8.00 (m, 2H), 7.43 (d, J = 8.8 Hz, 1H), 7.19 – 7.05 (m, 5H), 5.56 – 5.32 (m, 2H), 5.15 (d, J= 17.1 Hz, 1H), 4.38 – 4.34 (m, 1H), 4.16 – 4.11 (m, 1H), 3.95 – 3.83 (m, 1H), 3.07 – 2.99 (m, 4H), 2.40 (s, 3H), 2.38 – 2.34 (m, 1H), 2.01 – 1.98 (m, 1H), 1.56 – 1.48 (m, 2H), 1.41 – 1.33 (m, 2H).

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 591-55-9, 5-Aminopyrimidine.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (319 pag.)WO2017/35351; (2017); 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. 591-55-9, name is 5-Aminopyrimidine, molecular formula is C4H5N3, 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. Formula: C4H5N3

Pyrimidin-5-amine (9.84 mg, 0.104 mmol) was dissolved in DCM (1.0 mL) along with pyridine (0.039 mL, 0.487 mmol) and DIEA (0.032 mL, 0.183 mmol). Intermediate14SF (28 mg, 0.061 mmol) in 2 mL of DCM was added dropwise, and the reactionmixture was stirred at room temperature for 50 minutes. The reaction was quenched with1.0 N HC1 (0.5 mL). All solvent was removed under vacuum. The crude material wasdissolved in DMSO/THF (2:1, 6 mL) and purified via preparative LC/MS (method C,45-70% B over 30 mm, then a 5-mm hold at 100% B). Fractions containing the desiredproduct were combined and dried via centrifugal evaporation to yield Example 185 (1.6 mg, 4.3% yield). ?H NMR (500MHz, DMSO-d6) 8.86 (m, 3H), 8.76 (s, 1H), 8.60 (s, 1H), 7.90 (d, J=1 1.0 Hz, 1H), 7.85 (br. s., 1H), 5.45 (d, J7.9 Hz, 1H), 4.57 (d, J12.2 Hz, 1H), 4.45 (dd, J=12.2, 6.7 Hz, 1H), 4.09 (s, 3H), 3.68 (dd, J15.9, 9.8 Hz, 1H), 3.33 (d, J12.2 Hz, 1H), 2.64 (s, 3H); LC-MS: method C, 2 to 98% B. RT = 2.14 mm, MS(ESI) m/z: 519.30 (M+H) Analytical HPLC purity (method B): > 86%.

With the rapid development of chemical substances, we look forward to future research findings about 591-55-9.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; HALPERN, Oz Scott; JIANG, Wen; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (545 pag.)WO2018/13776; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 591-55-9, 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.591-55-9, name is 5-Aminopyrimidine, molecular formula is C4H5N3, molecular weight is 95.1, as common compound, the synthetic route is as follows.

6-(4-Chloro-phenyl)-5-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid (prepared as described in WO 2012/032018, Example AE) was combined with DMF (30 ml) at RT, to give a colorless solution. Pyrimidin-5 -amine, TBTU and N-Ethyldiisopropylamine were added. The reaction mixture was stirred at RT for 15 h. The reaction mixture was poured into 150 mL ]0 and extracted with EtOAc (2 x 150 mL). The combined organic layers were washed with brine, dried over MgS04 and evaporated. The crude material was purified by flash chromatography (silica gel, 20g, 0% to 50% EtOAc in hexane). LC-MS (ESI) 409.068 (M+H)+.

Statistics shows that 591-55-9 is playing an increasingly important role. we look forward to future research findings about 5-Aminopyrimidine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC; FORNONI, Alessia; (59 pag.)WO2020/21097; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 591-55-9, 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 591-55-9 as follows.

Example 203: Preparation of N4-cyclopropyI-N2-(pyrimidin-5-yl)-5-(trifluoromethyl) pyrimidine-2,4-diamin2-Chloro-N-cyclopropyl-5-(trifluoromethyl)pyrimidin-4-amine (0.070 g, 0.295 mmol) and pyrimidin-5-amine (0.028 g, 0.295 mmol) were mixed in Acetic Acid (1 ml). The mixture was microwaved at 120 C for 10 minutes and then concentrated. 3 mg of product was recovered after automated reverse phase chromatography (water-MeCN eluent). MS calcd for297.1 1 , found 296.90.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,591-55-9, its application will become more common.

Reference:
Patent; SALK INSTITUTE FOR BIOLOGICAL STUDIES; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; YALE UNIVERSITY; SHAW, Reuben J.; EGAN, Daniel F.; COSFORD, Nicholas; TURK, Benjamin; VAMOS, Mitchell; PANICKAR, Dhanya Raveendra; CHUN, Matthew; SHEFFLER, Doug; (315 pag.)WO2016/33100; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia