1500-85-2 | Pyrimidines

Some scientific research about 7H-Pyrrolo[2,3-d]pyrimidin-4-amine

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. 1500-85-2, 7H-Pyrrolo[2,3-d]pyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Synthetic Route of 1500-85-2 ,Some common heterocyclic compound, 1500-85-2, molecular formula is C6H6N4, 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.

Solid K2CO3 (0.930 g, 6.71 mmol, 3.0 equiv) was added to a stirringsolution of 7H-pyrrolo[2,3-d]pyrimidin-4-amine 16 (0.300 g,2.24 mmol, 1.0 equiv) in dry DMF (15 mL) at room temperature. After 1 h, a solution of tert-butyl (2-chloroethyl)carbamate (0.602 g,3.35 mmol, 1.5 equiv) in dry DMF (5 mL) was added dropwise. Theresulting suspensionwas stirred for 48 h at 80 C. After the reactionwas complete, as indicated by TLC, the crude material was filteredthrough a plug of Celite to remove inorganic salts and thenwashedwith dichloromethane (50 mL x 4). The filtratewas concentrated byrotary evaporation and purification was carried out using 9%methanol/dichloromethane as the eluent to provide a light brownsolid of the corresponding tert-butyl carbamate. This material wasdissolved in 15 mL of a 1:1 (v/v) mixture of trifluoroacetic acid anddichloromethane. The resulting solution was stirred at room temperaturefor 4 h before it was concentrated by rotary evaporation at35 C. The resulting trifluoroacetic acid salt of the deprotectedamine was dissolved in absolute ethanol (20 mL) and stirred withAmberlyst A-21 free base resin (4 g) at room temperature for 10 h.The heterogeneous reaction mixture was filtered and washed withmethanol (50 mL x 4) until the chromophorewas no longer evidentin the drippingwash by TLC. The filtratewas concentrated by rotaryevaporation and purified using 15% ammonia-saturated methanol/dichloromethane as the eluent to provide product D as a lightbrown solid in 58% yield (0.231 g, 1.30 mmol) from 16. m.p.145e146 C; 1H NMR (DMSO-d6, 500 MHz): d 8.03 (1H, s), 7.14 (1H,d, J 3.4 Hz), 6.90 (2H, br, s), 6.50 (1H, d, J 3.4 Hz), 4.07 (2H, t,J 6.6 Hz), 2.86 (2H, t, J 6.6 Hz), 1.57 (2H, br, s); 13C NMR(DMSO-d6, 125 MHz): d 157.37, 151.40, 149.55, 124.38, 102.35, 98.07,47.16, 41.99; HRMS: m/z calcd for C8H11N5,177.1014; found 177.1010.

Reference:
Article; Gibbons, Garrett S.; Chakraborty, Amarraj; Grigsby, Sierrah M.; Umeano, Afoma C.; Liao, Chenzhong; Moukha-Chafiq, Omar; Pathak, Vibha; Mathew, Bini; Lee, Young-Tae; Dou, Yali; Schuerer, Stephan C.; Reynolds, Robert C.; Snowden, Timothy S.; Nikolovska-Coleska, Zaneta; European Journal of Medicinal Chemistry; vol. 189; (2020);,
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New downstream synthetic route of 7H-Pyrrolo[2,3-d]pyrimidin-4-amine

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, 1500-85-2, 7H-Pyrrolo[2,3-d]pyrimidin-4-amine.

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. 1500-85-2, name is 7H-Pyrrolo[2,3-d]pyrimidin-4-amine. A new synthetic method of this compound is introduced below., Application In Synthesis of 7H-Pyrrolo[2,3-d]pyrimidin-4-amine

500 mg (3.7 mmol) of 7H-pyrrolo[2,3-d]pyrimidin-4-amine were dissolved in 40 mL of dry DMF and 1.03 g (3.7 mmol) of tert-butyl 4-[(methylsulfonyl)oxy]piperidine-1-carboxylate were added, followed by 3.87 g (3.7 mmol) of caesium carbonate, under argon atmosphere. The mixture was heated in a microwave apparatus at 100 C for 4 hours, then the solvent removed under vacuum.The residue was taken up with dicholomethane and washed with brine. Theorganic layer was dried over Na2S04 and evaporated to give, after trituration with diethyleher, 420 mg of the title compound. (36%)

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; ANGIOLINI, Mauro; BUFFA, Laura; MENICHINCHERI, Maria; MOTTO, Ilaria; POLUCCI, Paolo; TRAQUANDI, Gabriella; ZUCCOTTO, Fabio; WO2014/184069; (2014); A1;,
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Sources of common compounds: 7H-Pyrrolo[2,3-d]pyrimidin-4-amine

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1500-85-2, 7H-Pyrrolo[2,3-d]pyrimidin-4-amine, and friends who are interested can also refer to it.

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.1500-85-2, name is 7H-Pyrrolo[2,3-d]pyrimidin-4-amine, molecular formula is C6H6N4, molecular weight is 134.14, as common compound, the synthetic route is as follows.COA of Formula: C6H6N4

General procedure: Procedure G: To a solution of 7H-pyrrolo[2,3-d]pyrimidin-4-amine (1, 0.32 g, 2.39 mmol) and 2?-chloro-4?-methylspiro[cyclohexane-1,7?-pyrrolo[3,4-b]pyridin]-5?(6?H)-one (2, 0.6 g, 2.39 mmol) in 1,4-dioxane (15 mL) was added cesium carbonate (2.33 g, 7.17 mmol). The reaction mixture was purged with argon for 5 min. and then XanthPhos (69 mg, 0.11 mmol), XPhos (57 mg, 0.11 mmol), tris(dibenzylideneacetone)dipalladium(0) (109 mg, 0.11 mmol) and palladium acetate (27 mg, 0.11 mmol) were added and the reaction mixture purged for an additional 5 min. The purged reaction mixture was stirred at 100 C. for 4 h. After TLC showed completion, the reaction mixture was filtered through a bed of celite and the resulting filtrate was concentrated. The crude product was purified by preparative HPLC. The desired fractions were concentrated to dryness under vacuum to afford 2?-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-4?-methylspiro[cyclohexane-1,7?-pyrrolo[3,4-b]pyridin]-5?(6?H)-one as a yellow solid. Yield: 0.095 g, 11%;

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1500-85-2, 7H-Pyrrolo[2,3-d]pyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; EFFECTOR THERAPEUTICS, INC.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; (55 pag.)US2017/121339; (2017); A1;,
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Extracurricular laboratory: Synthetic route of 7H-Pyrrolo[2,3-d]pyrimidin-4-amine

The synthetic route of 1500-85-2 has been constantly updated, and we look forward to future research findings.

Adding a certain compound to certain chemical reactions, such as: 1500-85-2, 7H-Pyrrolo[2,3-d]pyrimidin-4-amine, 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: 7H-Pyrrolo[2,3-d]pyrimidin-4-amine, blongs to pyrimidines compound. name: 7H-Pyrrolo[2,3-d]pyrimidin-4-amine

To a solution of 7H-pyrrolo[2,3-d]pyrimidin-4-ylamine (1.3 g, 9.7 mmol, 1.0 eq) in CHC13 (45 mL) was added NIS (2.18 g, 9.7 mmol, 1.0 eq) at rt. The solution was refluxed for 2 h. The precipitate was filtered and dried in vacuo to give 5-iodo-7H- pyrrolo[2,3-d]pyrimidin-4-ylamine (2.09 g, 83%) as a white solid.

The synthetic route of 1500-85-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; QIAN, Shawn; (346 pag.)WO2018/11628; (2018); A1;,
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New learning discoveries about 7H-Pyrrolo[2,3-d]pyrimidin-4-amine

The chemical industry reduces the impact on the environment during synthesis 1500-85-2, I believe this compound will play a more active role in future production and life.

Synthetic Route of 1500-85-2, 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.1500-85-2, name is 7H-Pyrrolo[2,3-d]pyrimidin-4-amine, molecular formula is C6H6N4, molecular weight is 134.14, as common compound, the synthetic route is as follows.

To a solution of 200 mg (1.49 mmol) of 7H-pyrrolo[2,3-d]pyrimidin-4-amine in 4 mL of DMF, 235 muL of dimethylformamide dimethyl acetal were added. The mixture was stirred at room temperature overnight. The solvent was then removed in vacuo and the residue taken up with DCM, washed with brine, dried over anhydrous Na2SO4and evaporated to dryness. The crude was triturated with diisopropylether and filtered, to afford 204 mg (73%) of the title compound. 1H NMR (600 MHz, DMSO-cie) delta ppm 3.10 (s, 3 H) 3.16 (s, 3 H) 6.45 (dd, J=3.39, 1.92 Hz, 1 H) 7.21 (dd, J=3.11 , 2.38 Hz, 1 H) 8.28 (s, 1 H) 8.79 (s, 1 H) 11.60 (br. s., 1 H) HRMS (ESI) calcd for C9HnN5 [M+H]+ 190.1087, found 190.1085.

The chemical industry reduces the impact on the environment during synthesis 1500-85-2, I believe this compound will play a more active role in future production and life.

New downstream synthetic route of Related Products of 1500-85-2

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 1500-85-2, 7H-Pyrrolo[2,3-d]pyrimidin-4-amine.

Related Products of 1500-85-2, 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. 1500-85-2, name is 7H-Pyrrolo[2,3-d]pyrimidin-4-amine, molecular formula is C6H6N4, 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.

Scheme 3 NH2 NPhth XN phthalic anhydride XN N N DMAC N N H H 3-1 3-2 H H 3J. 32 To a 250 mL three-neck round bottom flask equipped with an overhead stirrer, nitrogen inlet, and thermocouple was charged 50 mL of dry N,N-dimethylacetamide followed by 5.0 g OF 7H-PYRROLO [2, 3-DLPYRIMIDIN-4-YLAMINE (U) [J. Davoll, J. Chem. SOC., 131-138 (1960)] and 11.6 g of phthalic anhydride. The resulting mixture was heated to 80 C for 8 h and then cooled to 10 C. Water (40 ML) was added while maintaining the temperature below 15 C. The resulting slurry was aged for 4 h, then filtered, and the filter washed with 20 ML of 1: 1 (v/v) dimethylacetamide/water followed by 30 ML of water. The cake was sucked dry, then washed with 50 ML of ethyl acetate. The solid was dried at 40 C under vacuum with a nitrogen sweep to give 8.1 g OF 4-PHTHALIMIDO-7H-PYRROLO [2, 3-d]pyrimidine (3-2); m. p. 276-277 C. LH NMR (DMSO-D6, 400 MHz) : 8 12. 14 (s, 1H), 8.79 (s, 1H), 8.01 (dd, J=5.5, 3.1 Hz, 2H), 7.92 (dd, J=5. 5,3. 1 HZ, 2H), 7.63 (dd, J=3.5, 2.4 Hz, 1H), 6.56 (dd, J=3.5, 1.8 Hz, 1H) ; 13C NMR (DMSO-D6, 100 MHZ) : 5 166.3, 154.2, 151.0, 145. 2,135. 7,132. 0,128. 7,124. 4,115. 2,100. 1.

Reference:
Patent; MERCK & CO. INC.; WO2004/72090; (2004); A1;,
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Extended knowledge of 1500-85-2

1500-85-2, 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. 1500-85-2, name is 7H-Pyrrolo[2,3-d]pyrimidin-4-amine, molecular formula is C6H6N4, 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.

General procedure: Procedure C: A solution of 4-methyl-7H-pyrrolo[2,3-d]pyrimidine (1, 0.4 g, 3.0 mmol), 5-bromo-2-(4-methoxybenzyl) isoindolin-1-one (2, 1.0 g, 4.5 mmol) and potassium phosphate (1.91 g, 9.0 mmol) in 1, 4-dioxane (15 ml) was degassed with nitrogen for 10 min. Copper (I) iodide (0.28 g, 1.5 mmol) and trans-1, 2-diaminocyclohexane (0.17 g, 1.5 mmol) were added and the reaction was refluxed at 90 C. for 16 h. Progress of the reaction was monitored by TLC. After completion, solvent was removed under reduced pressure. The reaction mixture was diluted with water and extracted twice with ethyl acetate. The organic layer was separated, dried over sodium sulphate, filtered and concentrated under reduced pressure to afford 2-(4-methoxybenzyl)-5-(4-methyl-7H-pyrrolo [2, 3-d] pyrimidin-7-yl) isoindolin-1-one (3) as a yellow solid. Yield: 0.55 g, 47%;

A new synthetic route of 1500-85-2

7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.4 g, 3.0 mmol) was dissolved in 10 mL DMF.NIS (0.74 g, 3.3 mmol) was added in portions under ice bath.After the feeding is completed, the ice bath is removed.The reaction was allowed to proceed at room temperature for 3 hours, and the reaction was confirmed to be complete by TLC. 20 mL of water was added to the reaction solution.It was extracted with ethyl acetate (30 mL*3), and the organic phase was washed with 20 mL of brine.Dry over anhydrous sodium sulfate, concentrate,The residue was separated into a pale yellow solid (0.56 g).The yield was 73%.

Reference:
Patent; Shenzhen Tajirui Bio-pharmaceutical Co., Ltd.; Wang Yihan; Xing Qingfeng; (59 pag.)CN110194772; (2019); A;,
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Simple exploration of 1500-85-2

The chemical industry reduces the impact on the environment during synthesis 1500-85-2, I believe this compound will play a more active role in future production and life.

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 1500-85-2 as follows., 1500-85-2

4-Amino-7H-pyrrolo [2,3-d] pyrimidine (0.60 g, 4.47 mmol) was weighedN-iodosuccinimide (1.51 g, 6.71 mmol)Dissolved in 100 ml of acetonitrile,And heated at 120 for 24h.After the reaction is completed, the solvent is evaporated,With dichloromethane mixed with water extraction,The organic phase was dried over anhydrous sodium sulfate and evaporated under reduced pressure.The residue was purified by column chromatography to give 0.96 g of a yellow solid (82.51% yield).

The chemical industry reduces the impact on the environment during synthesis 1500-85-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Sichuan University Huaxi Hospital; He Yang; Chai Yingying; Chen Bojiang; Zhou Xinglong; Li Changfu; Qiu Zhixin; Li Weimin; (11 pag.)CN106831790; (2017); A;,
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