| Identification | Back Directory | [Name]
5,7-DIMETHYL-PYRAZOLO[1,5-A]PYRIMIDINE-3-CARBOXYLIC ACID | [CAS]
90349-23-8 | [Synonyms]
133800 SBB006994 5677-29-2 ALINDA 7268 AKOS B001272 BAS 16984927 MLS000715307 SMR000275286 AKOS BBS-00002689 VITAS-BB TBB005266 TIMTEC-BB SBB006994 ART-CHEM-BB B001272 5,7-dimethyl-3-pyrazolo[1,5-a]pyrimidinecarboxylic acid 5,7-DIMETHYLPYRAZOLO[5,4-A]PYRIMIDINE-3-CARBOXYLIC ACID 5,7-DIMETHYL-PYRAZOLO[1,5-A]PYRIMIDINE-3-CARBOXYLIC ACID pyrazolo[1,5-a]pyrimidine-3-carboxylic acid, 5,7-dimethyl- 5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid(SALTDATA: FREE) | [Molecular Formula]
C9H9N3O2 | [MDL Number]
MFCD01051014 | [MOL File]
90349-23-8.mol | [Molecular Weight]
191.19 |
| Hazard Information | Back Directory | [Uses]
5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic Acid is used as a reactant in the synthetic preparation of noninhibitory small molecule chaperones of glucocerebrosidase. | [Synthesis]
General procedure for the synthesis of 5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid from ethyl 5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylate: to a solution of 5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl 5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylate (2.2g, 10.0mmol) in methanol (15mL), was added an aqueous sodium hydroxide solution (5.67 mL, 7.2 M) and the reaction mixture was heated to reflux at 80 °C for 5 hours. After the reaction was completed, it was cooled to room temperature and neutralized with 2M hydrochloric acid. After neutralization, a white solid precipitated from the solution, which was collected by filtration, washed sequentially with water and ether, and dried in vacuum to afford 5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid as a white solid (1.3 g, 68% yield). The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 8.21 (s, 1H), 6.84 (s, 1H), 2.65 (s, 3H), 2.53 (s, 3H). Electrospray mass spectrometry (ES-MS) showed m/z 192.00 ([M+H]+). | [References]
[1] Monatshefte fur Chemie, 2016, vol. 147, # 12, p. 2221 - 2234 [2] Patent: WO2016/73895, 2016, A1. Location in patent: Paragraph 00220 [3] Patent: WO2012/78855, 2012, A1. Location in patent: Page/Page column 17 [4] Journal of Medicinal Chemistry, 2012, vol. 55, # 12, p. 5734 - 5748 [5] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 1, p. 214 - 225 |
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