Category: 25940-35-6

Synthetic Route of 25940-35-6 , The common heterocyclic compound, 25940-35-6, name is Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid, molecular formula is C7H5N3O2, 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.

Thionyl chloride (8.92 mL, 123 mmol) was added to pyrazolo[l,5-a]pyrimidine- 3-carboxylic acid (0.2 g, 1.2 mmol) and the mixture was stirred for 2 h at 80 C. The solvent was then removed under reduced pressure and the material was left on the high-vacuum for 3 h. The material was used without further purification.

The synthetic route of 25940-35-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIM, Jongwon; ALTMAN, Michael, D.; CHILDERS, Matthew, L.; GIBEAU, Craig, R.; HO, Ginny Dai; TSUI, Honchung; (80 pag.)WO2016/144844; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 25940-35-6, Adding some certain compound to certain chemical reactions, such as: 25940-35-6, name is Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid,molecular formula is C7H5N3O2, 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 25940-35-6.

To a solution of 5-(5-bromo-2-(difluoromethoxy)phenyl)-l-((2- (trimethylsilyl)ethoxy)methyl)-lH-pyrazol-4-amine (50.1 g, 115 mmol) in DMA (1500 mL) was added pyrazolo[l,5-a]pyrimidine-3-carboxylic acid (32.1 g, 196.0 mmol), PyAOP (102 g, 196 mmol), DMAP (1.41 g, 11.0 mmol) and DIPEA (44.1 g, 0.341 mol). The resulting solution was stirred for 3h at 60C in an oil bath. The reaction was then quenched by the addition of 2000 mL of water/ice. The resulting solution was extracted with 3×2000 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 1×1000 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column eluting with ethyl acetate/petroleum ether (80%). The collected fractions were combined and concentrated under vacuum. The solid was stirred with 150 mL of H20 at rt, and the solid were collected by filtration. Dried in air. This resulted in 60.1 g (91%) of N-(5-(5-bromo-2-(difluoromethoxy)phenyl)-l-((2-(trimethylsilyl)ethoxy)methyl)-lH- pyrazol-4-yl)pyrazolo[l,5-a]pyrimidine-3-carboxamide as a light yellow solid. LCMS (Method G, ESI): [M+H]+= 579.1 & 581.1, RT= 1.10 min. 1H NMR (300 MHz, CDC13): delta (ppm) 9.62 (s, 1H), 8.80 (dd, J = 6.9, 1.7 Hz, 1H), 8.73 (s, 1H), 8.53 (dd, J = 4.2, 1.7 Hz, 1H), 8.38 (s, 1H), 7.79 (d, J = 2.4 Hz, 1H), 7.67 (dd, / = 8.8, 2.5 Hz, 1H), 7.29 (d, / = 1.4 Hz, 1H), 7.00 (dd, / = 6.9, 4.2 Hz, 1H), 6.43 (t, / = 72.6 Hz, 1H), 5.53 – 5.27 (m, 2H), 3.73 – 3.50 (m, 2H), 0.88 (ddd, / = 9.5, 6.4, 4.4 Hz, 2H), 0.00 (s, 9H).

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. 25940-35-6, Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; CHENG, Yun-Xing; GIBBONS, Paul; KELLAR, Terry; LI, Wei; MENDONCA, Rohan; YUEN, Po-wai; ZAK, Mark Edward; ZHANG, Lei; (212 pag.)WO2017/89390; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 25940-35-6 ,Some common heterocyclic compound, 25940-35-6, molecular formula is C7H5N3O2, 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.

(Benzotriazol-1 -yloxy)tripyrrolidinophosphonium hexafluorophosphate (1 .05 g, 2.02 mmol) was added to a mixture of pyrazolo[1 ,5-a]pyrimidine-3-carboxylic acid (299 mg, 1 .84 mmol, GAS No. 25940-35-6), trans-4-am ino-N-(2-chloro-4-fluorophenyl)cyclohexanecarboxam idehydrochloride (620 mg, 2.02 mmol) and N-ethyl-N-isopropylpropan-2-amine (1.6 ml, 9.2 mmol) in 20 ml N,N-dimethylformamide and the mixture was stirred over night at room temperature. For work-up, the reaction mixuture was concentrated under reduced pressure and the residue was stirred with a mixture of water and methanol. The precipitate was collected by filtration, washed with water and methanol and dried to yield the title compound(525mg, 68% yield).LG-MS (Method 1): R = 1 .01 mm; MS (ESIpos) m/z = 416.3 [M+H].1HNMR (400 MHz, DMSO-d6): 6 [ppm] = 9.51 (5, 1H), 9.38-9.28 (m, 1H), 8.88-8.76 (m, 1H),8.58 (5, 1H), 7.85-7.75 (m, 1H), 7.66-7.57 (m, 1H), 7.54-7.43 (m, 1H), 7.32-7.18 (m, 2H),3.91-3.67 (m, 1H), 2.12-2.01 (m, 2H), 2.01-1.89 (m, 2H), 1.67-1.49 (m, 2H), 1.47-1.27 (m,2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,25940-35-6, its application will become more common.

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

Application of 25940-35-6, Adding some certain compound to certain chemical reactions, such as: 25940-35-6, name is Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid,molecular formula is C7H5N3O2, 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 25940-35-6.

2,2-Dimethyl-6′-morpholino-spiro[1,3-dioxane-5,2′-3H-benzofuran]-5′-amine (90 mg, 0.28 mmol), pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (100 mg, 0.61 mmol), HATU (180 mg, 0.47 mmol) and N,N-diisopropylamine (0.2 ml, 1.22 mmol) was stirred in N,N-dimethylformamide (5 ml) at 25 oC for 12h. The mixture was concentrated and purified by column chromatography (eluent 40% ethyl acetate: petroleum ether) to afford N-(2,2-dimethyl-6′-morpholino-spiro[1,3- dioxane-5,2′-3H-benzofuran]-5′-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (110 mg, 84% yield).

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. 25940-35-6, Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BRYAN, Marian, C.; GOBBI, Alberto; KIEFER, James, Richard, Jr.; KOLESNIKOV, Aleksandr; OLIVERO, Alan, G.; DROBNICK, Joy; LIANG, Jun; RAJAPAKSA, Naomi; (846 pag.)WO2017/108723; (2017); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 25940-35-6, 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 25940-35-6, name is Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of [1-(5-amino-2,2-dimethyl-3H-benzofuran-6-yl)-4-piperidyl]methyl diethyl phosphate (79 mg, 0.14 mmol), pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (27 mg, 0.17 mmol), 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (78 mg, 0.21 mmol) and diisopropylethylamine (53 mg, 0.41 mmol) in N,N-dimethylformamide (5 mL) was stirred at 20 C for 1h. The mixture was purified by preparative HPLC (Xbridge 21.2*250mm c18, 10um; A: acetonitrile 25-55%; B: 10 mM ammonium bicarbonate in water) to afford [1-[2,2-dimethyl-5-(pyrazolo[1,5-a]pyrimidine-3-carbonylamino)-3H-benzofuran-6-yl]-4- piperidyl]methyl diethyl phosphate (7 mg, 9%) as yellow solid.1H NMR (400 MHz, CDCl3): delta 10.51 (s, 1H), 8.85 (dd, J = 1.6, 4.0 Hz, 1H), 8.79-8.76 (m, 2H), 8.44 (s, 1H), 7.10 (dd, J = 1.6, 7.2 Hz, 1H), 6.63 (s, 1H), 4.14 (q, J=7.2 Hz, 4H), 4.01-4.00 (m, 2H), 3.11 (d, J = 11.6 Hz, 2H), 3.03 (s, 2H), 2.69-2.64 (m, 2H), 1.87-1.77 (m, 5H), 1.48 (s, 6H), 1.35 (t, J = 6.8 Hz, 6H). MS (ESI): m/z = 558.3 [M+1]+.

According to the analysis of related databases, 25940-35-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BRYAN, Marian, C.; GOBBI, Alberto; KIEFER, James, Richard, Jr.; KOLESNIKOV, Aleksandr; OLIVERO, Alan, G.; DROBNICK, Joy; LIANG, Jun; RAJAPAKSA, Naomi; (846 pag.)WO2017/108723; (2017); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 25940-35-6, 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. 25940-35-6, name is Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid. A new synthetic method of this compound is introduced below.

To a solution of 5-[6-(difluoromethoxy)-3,4-dihydro-2H-l-benzopyran-7-yl]-l-[[2- (trimethylsilyl)ethoxy]methyl]-lH-pyrazol-4-amine (154 mg, 0.374 mmol) in DMA (3.0 mL) was added pyrazolo[l,5-a]pyrimidine-3-carboxylic acid (92.0 mg, 0.564 mmol), 4-DMAP (5.00 mg, 0.0409 mmol), DIPEA (145 mg, 1.12 mmol) and PyAOP (293 mg, 0.562 mmol). The reaction mixture was stirred at 45 C for 18 h. The reaction mixture was allowed to cool to RT and partitioned between ethyl acetate and water. The organic phase was washed with water and brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica gel chromatography eluting with ethyl acetate/petroleum ether (1/1) to afford N-[5-[6-(difiuoromethoxy)-3,4-dihydro-2H-l-benzopyran-7-yl]-l-[[2- (1224) (trimethylsilyl)ethoxy]methyl]- lH-pyrazol-4-yl]pyrazolo[ 1 ,5-a]pyrimidine-3-carboxamide (170 mg, 82%) as an off-white solid. LC/MS (Method F, ESI): [M+H]+ = 557, RT = 1.26 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,25940-35-6, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ROMERO, F. Anthony; ZAK, Mark; ZHAO, Guiling; GIBBONS, Paul; LI, Wei; CHENG, Yun-Xing; YUEN, Po-Wai; CHENG, Limin; (275 pag.)WO2018/122212; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 25940-35-6, Pyrazolo[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, Safety of Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid, blongs to pyrimidines compound. Safety of Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

To the mixture of pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (42 mg, 0.26 mmol) and diisopropylethylamine (0.09 mL, 0.52 mmol) in DMF (2 mL) was added 2-(7-aza-1H- benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (131 mg, 0.34 mmol) then the mixture was stirred at 25 oC for 15 min. To the mixture was added a solution of 2-[4-(5- amino-2,2-dimethyl-3H-benzofuran-6-yl)piperazin-1-yl]ethanol (50 mg, 0.17 mmol) in DMF (2 mL) and the resulting mixture was stirred at 25 oC for 16h. The mixture was purified by preparative HPLC(Xbridge 21.2*250 mm c18, 10um, A: acetonitrile 10-70%; B:10 mM ammonium bicarbonate in water) to afford N-[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2,2- dimethyl-3H-benzofuran-5-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide (45 mg, 60%) as a yellow solid.1H NMR (400 MHz,DMSO-d6) delta 10.42(s, 1H), 9.37(dd, J = 1.6 , 7.2Hz, 1H), 8.92 (dd, J = 1.6, 4.4Hz, 1H), 8.68(s, 1H), 8.31(s, 1H), 7.36(dd, J = 4.4,7.2Hz, 1H), 6.69(s, 1H), 4.45(t, J =5.2Hz, 1H), 3.54(q, J = 5.6 Hz, 2H), 3.00(s, 2H), 2.84-2.78(m, 4H), 2.74-2.61 (m, 4H), 2.50(t, J = 5.6 Hz ,2H), 1.41(s, 6H). MS (ESI): m/z = 437.3 [M+1]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,25940-35-6, Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BRYAN, Marian, C.; GOBBI, Alberto; KIEFER, James, Richard, Jr.; KOLESNIKOV, Aleksandr; OLIVERO, Alan, G.; DROBNICK, Joy; LIANG, Jun; RAJAPAKSA, Naomi; (846 pag.)WO2017/108723; (2017); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 25940-35-6, Adding some certain compound to certain chemical reactions, such as: 25940-35-6, name is Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid,molecular formula is C7H5N3O2, 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 25940-35-6.

PyBOP (298 mg, 572 pmol) was added to a mixture of 8-amino-3-(2-chlorophenyl)-1,3- diazaspiro[4.5]decane-2,4-dione (mixture of cis-/trans-isomers) (140 mg, 477 pmol, Intermediate 36), pyrazolo[1 ,5-a]pyrimidine-3-carboxylic acid (97.2 mg, 596 pmol) and N,Ndiisopropylethylamine (420 p1, 2.4 mmol) in DMF (1.7 ml) and the mixture was stirred overnight at room temperature. For work-up, water was added and the mixture was extracted with ethyl acetate. The combined organic phases were filtered through a silicone filter and concentrated. The residue was purified by preparative HPLC to give the title compound 45.0 mg (21 % yield).[C-MS (Method 2): R = 0.88 mm; MS (ESIneg): m/z = 437 [M-H]1HNMR (400 MHz, DMSO-d6): 6 [ppm] = 9.34-9.31 (m, 1H), 8.93 (5, 1H), 8.82 (dd, 1H), 8.59 (5, 1H), 8.11 (d, 1H), 7.68-7.64 (m, 1H), 7.56-7.45 (m, 3H), 7.29-7.25 (m, 1H), 4.14-4.04 (m, 1 H), 2.23-1.67 (m, 8H)

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. 25940-35-6, Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHGRABER, Philipp; WAGNER, Sarah; SUeLZLE, Detlev; BENDER, Eckhard; LI, Volkhart, Min-Jian; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; (232 pag.)WO2018/78009; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia