90349-23-8 | Pyrimidines

08/9/2021 News Share a compound : 90349-23-8

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90349-23-8, 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid, 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.90349-23-8, name is 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid, molecular formula is C9H9N3O2, molecular weight is 191.19, as common compound, the synthetic route is as follows.Application In Synthesis of 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid

General procedure: To a stirred solution of carboxylic acid compound (1.0 equivalent), HATU (1.5 equivalents), and DIPEA (3.75 equivalents) in DCM or DMF (~4 mL/0.2 mmol) was added amine compound (1.25 – 2.0 equivalents). The reaction mixture was stirred at roomtemperature for 4-16 hours, and then washed with saturated aqueous aHC03solution (5 mL/0.2 mmol), aqueous citric acid solution (5 mL/0.2 mmol) and brine (5 mL/0.2 mmol). The combined extracts were dried over anhydrous a2S04, filtered and concentrated in vacuo. The resulting crude material was purified by silica gel column chromatography or preparatory HPLC to give the amide compound. Following general procedure A, 5,7-dimethylpyrazolo[l,5-a]pyrimidine-3- carboxylic acid (40 mg, 0.21 mmol) and 1,2,3,4-tetrahydronaphthalen-l -amine afforded the title compound (37 mg, 55%) as a yellow solid.XH NMR (500 MHz, CDC13): delta 8.68 (s,1H),8.42 (d, J= 8.5 Hz, 1H), 7.47 (d, J= 7.0 Hz, 1H), 7.18-7.13 (m, 3H), 6.67 (s, 1H), 5.52- 5.49 (m, 1H), 2.91-2.84 (m, 2H), 2.78 (s, 2H), 2.53 (s, 3H), 2.25-2.22 (m, 1H), 2.00-1.90 (m, 3H). LC-MS m/z: 321.2 [M+H]+. HPLC Purity (214 nm): > 99 %; tR= 8.26 min.

Reference:
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; LANSBURY, Peter, T.; GOOD, Andrew, C.; BOURQUE, Elyse, Marie Josee; (139 pag.)WO2016/73895; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

New learning discoveries about 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,90349-23-8, its application will become more common.

Adding a certain compound to certain chemical reactions, such as: 90349-23-8, 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid, 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, 90349-23-8, blongs to pyrimidines compound. Formula: C9H9N3O2

A solution of 5,7-dimethylpyrazolo[l,5-a]pyrimidine-3-carboxylic acid 2 (200 mg, 1.04 mmol) in DMF (5 mL) was charged with EDC.HC1 (240 mg, 1.25 mmol), HOBT (170 mg, 1.25 mmol), triethyl amine (0.43 mL, 3.14 mmol) and stirred at room temperature for 30 mins. To the resulting solution was added methyl 4-(4-aminophenyl)butanoate (240 mg, 1.25 mmol) and the mixture was stirred at room temperature for 16h. Then, the reaction mixture was quenched with ice-cooled water (50 mL) and stirred for another 30 mins. The solid was collected by filtration and washed with water followed by w-hexane and dried to afford the corresponding ester as a light brown solid (240 mg) which was used in the next step without further purification. ES-MS m/z 367.40 (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,90349-23-8, its application will become more common.

Analyzing the synthesis route of 90349-23-8

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 90349-23-8, 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid.

Application of 90349-23-8, 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. 90349-23-8, name is 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid, molecular formula is C9H9N3O2, 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 5,7-dimethylpyrazolo[l,5-a]pyrimidine-3-carboxylic acid 2 (300 mg, 1.56 mmol) in DMF (10 niL) at 0C was charged with HATU (894 mg, 2.35 mmol), DIPEA (0.82 mL, 4.70 mmol) and 4-amino phenol (205 mg, 1.88 mmol). Then, the reaction mixture was warmed to room temperature and stirred for 16 h. The reaction mixture was quenched with water (2 mL), extracted with ethyl acetate (3 X 10 mL), dried over Na2S04and concentrated in vacuo to provide a crude product that was then purified by FCC (eluent, 5% methanol in DCM) to afford N-(4-hydroxyphenyl)-5,7-dimethylpyrazolo[l,5-a]pyrimidine-3-carboxamide as an off-white solid (284 mg, 64%). NMR (400 MHz, DMSO-i) delta 9.92 (s, 1H), 9.26 (s, 1H), 8.58 (s, 1H), 7.51 (d, J=7.9 Hz, 2H), 7.16 (s, 1H), 6.77 (d, J=7.9 Hz, 2H), 2.76 (s, 3H), 2.68 (s, 3H). ES-MS m/z 283.15 (M+H)+.

Extracurricular laboratory: Synthetic route of 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,90349-23-8, its application will become more common.

To a stirred solution of 5,7-dimethylpyrazolo[l,5-a]pyrimidine-3-carboxylic acid 2 (50 mg, 0.262 mmol), 2-methyl-lH-l,3-benzodiazol-6-amine (57 mg, 0.314 mmol) and HATU (149 mg, 0.393 mmol) in DMF (1 mL) was added DIPEA (0.14 mL, 0.786 mmol), and the reaction mixture was stirred at room temperature for 16 hours until the reaction was complete. The suspension was diluted with H20 (3 mL), and the precipitated solid was collected by filtration, washed with minimum DCM and Et20, and purified by prep-HPLC (MeCN/10 mM NH4HCO3) to give the title compound (28 mg, 33%) as a white solid.XH NMR (400 MHz, DMSO-i/6) 5 12.16 (s, 1H), 10.18 (d, J= 31.2 Hz, 1H), 8.63 (s, 1H), 8.09 (d, J= 53.2 Hz, 1H), 7.49-7.16 (m, 3H), 2.78 (s, 3H), 2.72 (s, 3H), 2.49 (s, 3H). ES-MS m/z: 321.1 [M+H]+. LC-MS Purity (254 nm): 99%; tR= 1.46 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,90349-23-8, its application will become more common.

Simple exploration of 90349-23-8

According to the analysis of related databases, 90349-23-8, the application of this compound in the production field has become more and more popular.

Reference of 90349-23-8, Adding some certain compound to certain chemical reactions, such as: 90349-23-8, name is 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid,molecular formula is C9H9N3O2, 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 90349-23-8.

To a suspension of the ester compound from the procedure above (105 mg, 0.340 mmol) in DMF (0.5 mL) was added a solution of l,2-benoxazol-5-amine (46 mg, 0.340 mmol) in DMF (0.5 mL). The reaction mixture was stirred at room temperature for 2 hours until the reaction was complete, and quenched with the addition of TFA (5 drops). The precipitated solid was collected by filtration, suspended in DCM, basified with saturated aHC03to pH ~8. The aqueous layer was extracted with DCM, dried over anhydrous a2S04, filtered andconcentrated to provide a residue. The residue was purified by prep-HPLC (MeCN/H20) to provide the title compound (40 mg, 38%) as a white solid.XH NMR (400 MHz, CDC13) delta 10.31 (s, 1H), 8.72-8.71 (m, 2H), 8.45 (d, J= 1.6 Hz, 1H), 7.67 (dd, J= 9.2 Hz, 2.0 Hz, 1H), 7.60 (d, J= 9.2 Hz, 1H), 6.79 (s, 1H), 2.84 (s, 3H), 2.74 (s, 3H). ES-MS m/z: 308.0 [M+H]+. HPLC Purity (214 nm): 98%; tR= 9.36 min.

According to the analysis of related databases, 90349-23-8, the application of this compound in the production field has become more and more popular.

New learning discoveries about 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid

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. 90349-23-8, 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Related Products of 90349-23-8 ,Some common heterocyclic compound, 90349-23-8, molecular formula is C9H9N3O2, 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.

Step (d) N-((l s,4s)-4-(5-Fluoro-2-(4 ‘-((4-(2-hydroxy ethyl)- 1 ,4-diazepan- l-yl)methyl)-2 ‘- (((SJ-S-methylmorpholinoJmethylJbiphenyl-S-yloxyJnicotinamidoJcyclohexylJ-S^- dimethylpyr azolo [ 1 ,5-a] pyrimidine-2-carboxamideTo a suspension of N-((ls,4s)-4-aminocyclohexyl)-5-fluoro-2-(4′-((4-(2-hydroxyethyl)-l,4- diazepan- 1 -yl)methyl)-2’-(((S)-3 -methylmorpholino)methyl)biphenyl-3 -yloxy Nicotinamide hydrochloride (200 mg, 0.24 mmol) in acetonitrile (2.74 ml) was added 5,7- dimethylpyrazolo[l,5-a]pyrimidine-2-carboxylic acid (48.9 mg, 0.26 mmol) and triethylamine (0.340 ml, 2.44 mmol). 1-Propanephosphonic acid cyclic anhydride, 1.57M solution in THF (0.171 ml, 0.27 mmol) was then added and the mixture stirred at RT for 2 hours. The mixture was evaporated to dryness and the residue dissolved in DCM (150 ml) and washed with saturated NaHCC^aq), brine, dried (MgSC^) and evaporated to give a foam. The crude product was purified by preparative HPLC using a 95-5% gradient of aqueous 0.2% ammonia in methanol as eluent to give the title compound as a white solid. Yield: 33 mg 1H NMR (W MHz, CDCl3) delta 8.11 – 8.03 (m, 2H), 7.48 – 7.37 (m, 2H), 7.22 – 7.14 (m, 3H), 7.12 – 7.07 (m, 2H), 6.88 (d, J= 6.9 Hz, 2H), 4.20 – 4.09 (m, IH), 4.06 – 3.96 (m, IH), 3.89 (d, J= 13.1 Hz, IH), 3.63 – 3.54 (m, 4H), 3.52 – 3.31 (m, 9H), 3.31 – 3.26 (m, 2H) 3.09 – 2.96 (m, 2H), 2.81 – 2.70 (m, 4H) 2.69 – 2.59 (m, 4H), 2.53 (s, 3H), 2.44 – 2.36 (m, IH), 2.23 – 2.11 (m, IH), 1.96 – 1.68 (m, 10H), 0.75 (d, J= 6.2 Hz, 3H). MS: [M+H]+=848 (calc=848) (MultiMode+)

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/144494; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Share a compound : 90349-23-8

Application of 90349-23-8 ,Some common heterocyclic compound, 90349-23-8, molecular formula is C9H9N3O2, 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 5,7-dimethylpyrazolo[l,5-a]pyrimidine-3-carboxylic acid 2 (50 mg, 0.262 mmol), 2,3-dihydro-lH-inden-5-amine (42 mg, 0.314 mmol) and HATU (149 mg, 0.393 mmol) in DMF (1 mL) was added DIPEA (0.1 mL, 0.524 mmol), and the reaction mixture was stirred at room temperature for 16 hours until the reaction was complete. The reaction mixture was purified by reverse phase chromatography (MeCN/10 mM NH4HCO3) to give the title compound (37 mg, 46%) as a white solid.XH NMR (400 MHz, DMSO-i) delta 10.11 (s, 1H), 8.62 (s, 1H), 7.66 (s, 1H), 7.46 (dd, J= 8.0 Hz, 2.0 Hz, 1H), 7.22-7.19 (m, 2H), 2.90- 2.82 (m, 4H), 2.77 (s, 3H), 2.71 (s, 3H), 2.07-1.99 (m, 2H). ES-MS m/z: 307.2 [M+H]+. LC- MS Purity (254 nm): >99%; tR= 1.98 min.

Some scientific research about 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid

Statistics shows that 90349-23-8 is playing an increasingly important role. we look forward to future research findings about 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid.

Synthetic Route of 90349-23-8, 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.90349-23-8, name is 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid, molecular formula is C9H9N3O2, molecular weight is 191.19, as common compound, the synthetic route is as follows.

A mixture of 5,7-dimethylpyrazolo[l,5-a]pyrimidine-3-carboxylic acid 2 (50 mg, 0.26 mmol), 4-methyl-3-(l,3-oxazol-2-yl)aniline (55 mg, 0.314 mmol) and HATU (57 mg, 0.39 mmol) in DMF/NMM (1 mL/0.1 mL) was stirred at room temperature for 12 hours. The reaction mixture was added with water (2 mL), stirred at room temperature for 0.5 hour and then filtered. The resulting solid was washed with water (1 mL), DCM (2 mL), Et20 (2 mL) and dried in vacuo to give the title compound (62 mg, 68.0%) as a white solid.XH NMR (400 MHz, DMSO) delta 10.22 (s, 1H), 8.64 (s, 1H), 8.45 (s, 1H), 8.27(s, 1H), 7.66 (s, 1H), 7.45 (m, 1H), 7.36-7.39 (m, 1H), 7.21 (s, 1H), 2.77 (s, 3H), 2.72 (s, 3H), 2.61 (s, 3H). ES-MS m/z: 348.1 [M+H]+. LC-MS Purity (254 nm): > 99%; tR= 1.91 min.

Statistics shows that 90349-23-8 is playing an increasingly important role. we look forward to future research findings about 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid.

Some scientific research about 90349-23-8

Reference of 90349-23-8, 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. 90349-23-8, name is 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid. A new synthetic method of this compound is introduced below.

A solution of 5,7-dimethylpyrazolo[l,5-a]pyrimidine-3-carboxylic acid 2 (120 mg, 0.62 mmol), HOBt (125 mg, 0.93 mmol), EDCI (144 mg, 0.93 mmol) in DMF (5 mL) was stirred at room temperature for 30 min and charged with 4-ethynylcyclohexan-l -amine (92 mg, 0.75 mmol) and stirred for another 16 h at room temperature. The reaction mixture was diluted with water (10 mL), extracted with ethyl acetate (3 X 10 mL), dried over a2S04and concentrated in vacuo. The crude compound which was purified by FCC (eluent, 2-4% methanol in DCM) to afford the title compound as a white solid (120 mg, 65%).XH NMR (400 MHz, CDC13) delta 8.61 (s, 1H), 8.04 (d, J=5.73 Hz, 1H), 6.70 (br s, 1H), 4.06-4.16 (m, 1H), 2.78(s, 3H), 2.67 (s, 1H), 2.63 (s, 3H), 2.29-2.41 (m, 1H), 2.16 (d, J=10.58 Hz, 2H), 2.12-1.84 (m, 2H), 1.34-1.43 (m, 2H), 1.22-1.31 (m, 2H). ES-MS m/z 297.25 (M+H)+. HPLC purity 99.9%

Application of 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid

With the rapid development of chemical substances, we look forward to future research findings about 90349-23-8.

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. 90349-23-8, name is 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid, molecular formula is C9H9N3O2, 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. Recommanded Product: 90349-23-8

(Benzotriazol-1 -yloxy)tripyrrolidinophosphonium hexafluorophosphate (980 mg, 1 .88 mmol)was added to a mixture of 5,7-dimethylpyrazolo[1 ,5-a]pyrimidine-3-carboxylic acid (300 mg,1 .57 mmol, GAS no 90349-23-8), trans-4-aminocyclohexanecarboxylate hydrochloride (274mg, 1.41 mmol, Gas No. 61367-07-5) and N-ethyl-N-isopropylpropan-2-amine (1.1 ml, 6.3mmol) in N,N-dimethylformamide (9.8 ml) and the mixture was stirred for 3 h at roomtemperature. For work-up the reaction mixuture was concentrated under reduced pressure. The residue was dissolved with dichloromethane and the organic phase was washed with water, filtrated through a silicone filter and concentrated. The crude product crystalized upon standing to give methyl trans-4-{[(5,7-dimethylpyrazolo[1 ,5-a]pyrim idin-3-yl)carbonyl]amino}cyclohexanecarboxylate (237 mg, 45% yield).LG-MS (Method 1): R = 1 .01 mm; MS (ESIneg) m/z = 329.2 [M-H]-.1HNMR (400 MHz, DMSO-d6): 6 [ppm] = 8.49 (5, 1H), 7.97 (d, 1H), 7.12 (d, 1H), 3.86-3.70(m, 1H), 3.61 (5, 3H), 2.74 (d, 3H), 2.62 (5, 3H), 2.43-2.31 (m, 1H), 2.08-1.90 (m, 4H), 1.58-1.29 (m, 4H).

With the rapid development of chemical substances, we look forward to future research findings about 90349-23-8.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia