Pyrimidines

Reference of 330786-24-8, 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 330786-24-8, name is 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

Step 3. A suspension of 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (400 mg, 1.3 mmol, 1.00 equiv), 2-(3-bromo-2,2-dimethylpropyl)-2,3-dihydro-1H-isoindole-1,3-dione (570 mg, 1.95 mmol, 1.50 equiv) and cesium carbonate (847 mg, 2.60 mmol, 2.00 equiv) in NMP (50 mL) was stirred at 100 C for 12 h under nitrogen atmosphere. It was quenched with water (150 mL). The resulting solution was extracted with ethyl acetate (5 x 30 mL). The organic layers were combined, dried over sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column eluting with dichloromethane/methanol (10 /1). This resulted in 280 mg (41%) of 2-(2-[[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-2-methylpropyl)-2,3-dihydro-1H-isoindole-1,3-dione as a yellow oil.

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 330786-24-8, 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine.

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; BABLER, Martin; GERRITSEN, Mary E.; WO2014/22569; (2014); A1;,
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Pyrimidine – Wikipedia

Related Products of 1337532-51-0 , The common heterocyclic compound, 1337532-51-0, name is 5-Bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine, molecular formula is C7H7BrN4, 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 stirred solution of 4-benzyl- 1 -(4-bromo-3-fl uorophenyl)- 1 H- 1,2 ,4-triazol-5(4H)- one (0.520 g, 1.494 mmol, 1.0 equiv), was added bis(pinacolato)diboron (0.130 g, 1.494 mmol, 1.0 equiv), potassium acetate (0.440 g, 1.494 mmol, 3.0 equiv), and the mixture was degassed with Argon for 10 mi PdCI2(dppf)-CH2CI2 adduct (0.061 g, 0.075 mmol,0.05 equiv) was added and again degassed with Argon for 10 mm. The reaction mixture was stirred for 5h at 100 00 in a sealed vessel. The reaction mixture was cooled to room temperature, 5-bromo-7-methyl-7H- pyrrolo[2,3-d]pyrimidin-4-amine (0.340 g, 1.494 mmol, 1.0 equiv) and saturated aqueous NaHCO3 (5 mL) was added to the reaction mixture and Argon gas was bubbled through the mixture for 10 mi PdCI2(dppf)-CH2CI2 adduct (0.061 g, 0.075 mmol,0.05 equiv ) was added to the reaction mixture, the vessel was sealed and the reaction mixture was stirred overnight at 100 00 . The reaction mixture was cooled to room temperature and filtered through celite, the filtrate was dried over Na2SO4 and concentrated. The crude material was purified by flash column chromatography using silicagel column using 4-5 % MeOH in DCM as an eluent to obtain 1-(4-(4- ami no-7-methyl-7H-pyrrolo[2 ,3-d]pyrimidin-5-yl)-3-fluorophenyl)-4-benzyl- 1 H-i ,2,4-triazol- 5(4H)-one as off white solid (0.044 g, 7.1 %). LCMS (ES) m/z = 416.2 [M÷H]. 1H NMR (400 MHz, DMSO-d6) O ppm 3.74 (5, 3H), 4.91 (5, 2H), 6.03 (br.s, 2H), 7.33 – 7.41 (m, 6H), 7.48 (t, J = 9.2 Hz, 1H), 7.84 (t, J = 6.0 Hz, 2H), 8.14 (5, 1H), 8.42 (5, 1H). 99.79% of purity by HPLC 254 nM.

The synthetic route of 1337532-51-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AXTEN, Jeffrey Michael; FAUCHER, Nicolas Eric; DAUGAN, Alain Claude-Marie; (110 pag.)WO2017/46738; (2017); A1;,
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Reference of 99586-66-0 ,Some common heterocyclic compound, 99586-66-0, 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.

General procedure: d) At rt, a solution of intermediate Xl (1 eq.) and an aryl halogenide VIII (1 to 2.5 eq.) in alcohol (nBuOH or EtOH, 0.08M to 0.1M) was treated with DIPEA (2 to Seq.) and irridiated in a microwave reactor or heated in an oil bath at 120-160C for 0.5 h to 6 d. Purification of intermediates and final products IX was carried out by flash chromatography,HPLCorSFC.

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. 99586-66-0, 2-Amino-4-chloro-6-methylpyrimidine-5-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; DU, Zhenxing; HINTERMANN, Samuel; HURTH, Konstanze; JACQUIER, Sebastien; LEHMANN, Hansjoerg; MOEBITZ, Henrik; SOLDERMANN, Nicolas; STOJANOVIC, Aleksandar; WO2015/10641; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 123148-78-7 ,Some common heterocyclic compound, 123148-78-7, 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.

Example 49; 4-Chloro-5-iodo-7-(2-trimethylsilanyl-ethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine (49.1); To a suspension of sodium hydride (60% in mineral oil, 78.8 g, 1.97 mmol) in dry THF (15 ml_), is added a solution of intermediate 38.2 (0.50 g, 1.79 mmol) in THF (5 ml.) dropwise and the resulting mixture is stirred for 15 min. It is then cooled to O0C and SEM chloride (0.33 ml_, 1.881 mmol) is added and the reaction mixture is stirred overnight. The reaction is quenched by carefully adding aqueous NH4CI and then extracted with EtOAc. The combined organic layer is successively washed with water, brine, dried over anhydrous Na2SO4 and concentrated in vacuo. Purification of the crude residue by column chromatography (silica 100-200 mesh, hexane : ethyl acetate = 92 : 8) gives intermediate 49.1 as a white solid, m p 108-1100C. 1H NMR (400 MHz, DMSOd6): delta 8.64 (s, 1 H), 7.53 (s, 1 H), 5.61 (s, 1 H), 3.53 (d, J = 8.29 Hz, 1 H); 0.92 (d, J = 8.29 Hz, 1 H); -0.03 (s, 9H). ESI-MS: calcd. for Ci2H17CIIN3OSi (409.73); found: 410 [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,123148-78-7, its application will become more common.

Reference:
Patent; NOVARTIS AG; CHEN, Yen-Liang; DURAISWAMY, Jeyaraj; KONDREDDI, Ravinder Reddy; YIN, Zheng; WO2010/15637; (2010); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 153286-94-3, 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 153286-94-3, name is 5-Ethynylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

[0242] Synthesis of (S)-tert-butyl (l-(3-bromo-6 pyimidin-5-ylemynyl)pyridm-2-yl)-2-(3,5- difluorophenyl)ethyl)carbamate (1G): (S)-tert-butyl (l-(3,6-dibromopyridin-2-yl)-2-(3,5- difluorophenyl)ethyl)carbamate (1G, 50 mg, 0.1 mmol) and 5-emynylpyrimidine (11.5 mg, 0.11 mmol) in THF (0.2 mL) was degassed and purged with argon. To it was added TEA (0.05 mL), Pd(PPh3)2Cl2(7 mg, 0.01 mmol) and Cul (2 mg, 0.01 mmol). The reaction was stirred for 2 hr at 40 °C and then cooled to ambient temperature. The reaction mixture was partitioned between EtOAc and 0 (plus 0.1 mL of ammonia). The organics were separated, dried, and removed in vacuo. The residue purified by column chromatography on silica to provide the title compound. MS (m/z) 516.66 [M+H]+.

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 153286-94-3, 5-Ethynylpyrimidine.

Reference:
Patent; GILEAD SCIENCES, INC.; BRIZGYS, Gediminas; CANALES, Eda; HALCOMB, Randall, L.; HU, Yunfeng, Eric; KATO, Darryl; LINK, John, O.; LIU, Qi; SAITO, Roland, D.; TSE, Winston, C.; ZHANG, Jennifer, R.; (253 pag.)WO2016/33243; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 155-10-2 , The common heterocyclic compound, 155-10-2, name is 4-Amino-2-chloro-5-fluoropyrimidine, molecular formula is C4H3ClFN3, 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 stirred solution of 4-AMINO-2-CHLORO-5-FLUOROPYRIMIDINE (4.22 g, 28. 6 mmol) in anhydrous THF (60 ml) and anhydrous pyridine (8 ml) under nitrogen was added dropwise over 5 min a solution of DI-TERT-BUTYL dicarbonate (15.60 g, 71. 5 mmol) in THF (10 + 2 ml). The solution was stirred at room temperature under nitrogen for 22.25 h. More DI-TERKBUTYL dicarbonate (3.12 g, 14.3 mmol) in THF (2 + 1 ml) was added and the solution was stirred for a further 3 days. The solvent was removed in vacuo and the residue was purified by flash chromatography, eluting with 15% ETOAC/ISOHEXANE, to leave 14.77 g of a 1: 0. 88 mixture OF DI-TE+BUTYL 2-CHLORO-5-FLUOROPYRIMIDIN-4-YLIMIDODICARBONATE and DI-TE+BUTYL dicarbonate as a white solid.

The synthetic route of 155-10-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2004/65388; (2004); A1;,
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. 1060816-58-1, name is 5-Bromo-2-chloro-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 5-Bromo-2-chloro-7H-pyrrolo[2,3-d]pyrimidine

To a suspension of 5-bromo-2-chloro-7H-pyrrolo[2,3-djpyrimidine (0.13 g, 0.50 mmol) and cis-4-.(tert-butyldimethylsilyloxy)cyclohexanol (0.23g, 1.0 mmol) in toluene (8 mL) was added (cyanomethylene)trimethylphosphorane (CMMP; prepared according toChem. Pharm. Bull. 2003, 51(4), 474-476.) (6.3 mL, 0.16 M in THF, 1.0 mmol). The resulting clear solution was refluxed for 16 h. The reaction mixture was washed with brine, and extracted with EtOAc (3X). The combined organic layer was dried (Na2504) and concentrated. The residue was purified on ISCO to provide the desired product (0.16 g, 72%). 1H NMR (400 MHz, CD3OD) oe 8.71 (s, 1H), 7.27 (s, 1H), 4.70 (tt, J = 12.2, 3.9 Hz, 111),3.69 (tt, J = 10.5, 4.2 Hz, 1H), 2.09- 1.99 (m, 3H), 1.86- 1.71 (m, 2H), 1.66- 1.54 (m, 3H),0,90 (s, 9H), 0.08 (s, 6H). MS m/z 444.2 [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, 1060816-58-1, 5-Bromo-2-chloro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; EARP, Henry Shelton, III; (109 pag.)WO2017/62797; (2017); 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.1820-81-1, name is 5-Chlorouracil, molecular formula is C4H3ClN2O2, molecular weight is 146.53, as common compound, the synthetic route is as follows.Computed Properties of C4H3ClN2O2

Method 3 2,4,5-Trichloropyrimidine 5-Chlorouracil (10.0 g, 68.5 mmol) was dissolved in phosphorus oxychloride (60 ml) and phosphorus pentachloride (16.0 g, 77.0 mmol) was added. The mixture was heated under reflux for 16 hours, left to cool and then poured slowly into water (200 ml) with vigorous stirring. The mixture was stiffed for 1.5 hours and then ethyl acetate (250 ml) was added. The organic layer was separated and the aqueous layer was extracted with a further portion of ethyl acetate (250 ml). The combined extracts were washed with saturated sodium bicarbonate (200 ml) and saturated sodium chloride solution (200 ml), and then dried. Volatile material was removed by evaporation and the residue was purified by column chromatography, eluding with DCM, to give the product as a yellow liquid (6.37 g, 51%). NMR (CDCl3): 8.62 (s, 1H); MS (MH+): 182, 184, 186.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1820-81-1, 5-Chlorouracil, and friends who are interested can also refer to it.

Reference:
Patent; Pease, Elizabeth Janet; Breault, Gloria Anne; Williams, Emma Jane; Bradbury, Robert Hugh; Morris, Jeffrey James; US2003/149266; (2003); 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. 876343-10-1, name is 4-Chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H3ClIN3, 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. SDS of cas: 876343-10-1

General procedure: Compound 1a-d or 54 (1 mmol) was mixed with the selected amine, 2-25, (3 mmol) and n-butanol (5 ml) and agitated at145 C for 14-24 h. Then the mixture was cooled to 22 C, dilutedwith water (15 ml) and ethyl acetate (40 ml). After phase separation,the water phase was back extracted with more ethyl acetate(2 10 ml). The combined organic phases were washed with brine(10 ml), dried over anhydrous Na2SO4, filtered and concentrated invacuo, before the crude mixture was purified as specified for eachindividual compound

With the rapid development of chemical substances, we look forward to future research findings about 876343-10-1.

Reference:
Article; Kaspersen, Svein Jacob; Han, Jin; N°rsett, Kristin G.; Rydsa, Line; Kj°bli, Eli; Bugge, Steffen; Bj°rk°y, Geir; Sundby, Eirik; Hoff, Bard Helge; European Journal of Pharmaceutical Sciences; vol. 59; 1; (2014); p. 69 – 82;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1780-40-1 ,Some common heterocyclic compound, 1780-40-1, molecular formula is C4Cl4N2, 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 a 250 mL three-neck flask fitted with a degassing tube and temperature probe, acetonitrile (100 mL) and water (25 mL) were degassed with nitrogen for 30 min while stirring. 2,4,5,6-Tetrachloropyrimidine (8.77 g, 0.0402 mol, 1.5 equiv) and triphenylphosphine (0.70 g, 2.6 mmol, 0.1 equiv) were added and degassed for 15 min. 5-Chloro-2-methoxyphenylboronic acid (5.00 g, 0.0268 mol, 1.0 equiv), potassium phosphate (11.39 g, 0.0536 mol, 2.0 equiv) and palladium acetate (301 mg, 1.3 mmol, 0.05 equiv) were added and degassed for 5 min. The reaction was complete after 2 h at room temperature. The reaction mixture was added to 250 mL CH2Cl2. The organic layer was washed twice with water (125 mL), dried over Na2SO4, and concentrated. The crude product was purified by silica gel column chromatography. The product was obtained as a white solid (5.97 g, 69%). 1H NMR (500 MHz, CDCl3, delta): 7.45 (dd, J=8.9, 2.6 Hz, 1H), 7.31 (d, J=2.6 Hz, 1H), 6.94 (d, J=8.9 Hz, 1H), 3.82 (s, 3H); MS (ESI+): calculated for C11H6Cl4N2O, 321.92; m/z found, 323.0 [M+H+].

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. 1780-40-1, 2,4,5,6-Tetrachloropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Fitzgerald, Anne E.; Liu, Jing; Mani, Neelakandha S.; US2009/76268; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia