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.
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.
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,
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