5-Chloro-3-iodopyrazolo[1,5-a]pyrimidine
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![5-Chloro-3-iodopyrazolo[1,5-a]pyrimidine structure](https://file.echemi.com/fileManage/upload/canonicalSmiles/20220812/8cc2b861bd7548729268dbfddfd6af1b.png "5-Chloro-3-iodopyrazolo[1,5-a]pyrimidine")
5-Chloro-3-iodopyrazolo[1,5-a]pyrimidine
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CAS No:
923595-58-8
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Formula:
C6H3ClIN3
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Chemical Name:
5-Chloro-3-iodopyrazolo[1,5-a]pyrimidine
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Synonyms:
5-Chloro-3-iodopyrazolo[1,5-a]pyrimidine;5-Chloro-3-iodo-pyrazolo[1,5-a]pyrimidine;Pyrazolo[1,5-a]pyrimidine, 5-chloro-3-iodo-;SCHEMBL3037759;CTK5H1192;KS-00000HQD;DTXSID80677471;ANW-50876;MFCD13193346;ZINC64033541
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CAS No:
5-Chloro-3-iodopyrazolo[1,5-a]pyrimidine Basic Attributes
279.464
278.906006
DTXSID80677471
2933990090
Safety Information
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
5-Chloro-3-iodopyrazolo[1,5-a]pyrimidine Use and Manufacturing
To a solution of 5-chloropyrazolo[1, 5-a]pyrimidine (200 mg, 1.30 mmol) in DMF (2 mL) was added N-iodosuccinimide (322 mg, 1.86 mmol). The reaction was stirred at rt overnight, then diluted with EtOAc (100 mL), and washed with HTo a solution of 5-chloropyrazolo[1, 5-a]pyrimidine (1.00 g, 6.51 mmol) in DMF (13 mL) was added portionwise N-iodosuccinamide (1.61 g, 7.16 mmol) at room temperature. N-Iodosuccinimide (1.61 g, 7.16 mmol) was added to a solutionof 5-chloropyrazolo[1, 5-a]pyrimidine (7) (1 g, 6.51 mmol) in anhydrousDMF (10 mL). After stirring at RT for 4 h the reaction was poured into 10percent sodium thiosulfate (75 mL). The resulting precipitate was isolated via filtration and dried (Whatman PS1 filterpaper) to give 19 as a pale brown solid (1.62 g, 89percent). 1H NMR δH (d6-DMSO, 300 MHz), 9.19 (d, J 7.2, 1H), 8.38 (s, 1H), 7.18 (d, J7.2, 1H). LC–MS tR 6.37 min; LC254 99percent; m/z 280.1/282.0 [M+H].This was used without further purification.To a solution of (R)-3-iluotO-2-(pyrrolidin-2-yl)pyridine (1 163 mg, 4.302 mmol) and 5-chloro-3-iodopyrazolo[l, 5-a]pyrimidine (1.76 g, 6.298 mmol) in DMF (15 mL) was DIPEA (4.9 mL, 27.99 mmol). The mixture was stirred at 110 C for 1 hour and then cooled to rt overnight. The mixture was extracted with AcOEt, dried and concentrated. The product was purified by column chromatography using 0-100% acetone in hexane. Product was isolated as an orange oil (1.42 g, 50%).
Computed Properties
Molecular Weight:279.46
XLogP3:1.9
Hydrogen Bond Acceptor Count:2
Exact Mass:278.90602
Monoisotopic Mass:278.90602
Topological Polar Surface Area:30.2
Heavy Atom Count:11
Complexity:157
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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5-Chloro-3-iodopyrazolo[1,5-a]pyrimidine
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