Pyrazolo[1,5-a]pyrimidine
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![Pyrazolo[1,5-a]pyrimidine structure](https://file.echemi.com/fileManage/upload/canonicalSmiles/20220812/11e82e4484634204b6e41f42fea1138c.png "Pyrazolo[1,5-a]pyrimidine")
Pyrazolo[1,5-a]pyrimidine
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CAS No:
274-71-5
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Formula:
C6H5N3
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Chemical Name:
Pyrazolo[1,5-a]pyrimidine
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Synonyms:
Pyrazolo[1,5-a]pyrimidine;1,4,7a-Triazaindene
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CAS No:
Safety Information
36/37
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Pyrazolo[1,5-a]pyrimidine Use and Manufacturing
Preparation of compound 23a: pyrazolo[1, 5-a]pyrimidineA mixture of 1 H-pyrazol-3-ylamine (32 g, 0.386 mol) and (E)-3-dimethylamino- propenal (38.2 g, 0.386 mol) in EtOH (500 ml_) was refluxed for 6 h. The solvent was removed in vacuo and the residue was purified via column chromatography (petroleum ether/EtOAc = 10:1 -2:1 ) which gave the title compound 23a as a white solid (30 g, 65percent).To a solution of pyrazolo[1, 5-ajpyrimidine (1 g, 8.39 mmol) in acetonitrile (5 mL) was added NBS (1.494 g, 8.39 mmol) and the reaction mixture stirred at room temperature for 8 h. The reaction mixture was concentrated under reduced pressure and the residue purified by silica gel chromatography (0-30% petroleum ether/EtOAc) to afford 3-bromopyrazolo[1, 5-ajpyrimidine (1.2 g, 6.06 mmol, 72% yield) as a brown solid. LCMS (ESI) m/e 198.0 [(M+H), calcd for C6H5BrN3198.01; LC/MS retention time (method A2): tR = 1.43 mm.
Human drugs -> Rare disease (orphan)