6-Bromo-2-chloroquinazoline
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6-Bromo-2-chloroquinazoline
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CAS No:
882672-05-1
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Formula:
C8H4BrClN2
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Chemical Name:
6-Bromo-2-chloroquinazoline
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Synonyms:
6-bromo-2-chloroquinazoline;QUINAZOLINE, 6-BROMO-2-CHLORO-;MFCD09261000;6-Bromo-2-chloro-quinazoline;PubChem14677;2-chloro-6-bromoquinazoline;Quinazoline,6-bromo-2-chloro-;SCHEMBL1570789;CTK5F9562;DTXSID80591582
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CAS No:
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|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
6-Bromo-2-chloroquinazoline Use and Manufacturing
A solution of 6-bromoquinazolin-2-ol (9.72 g, 40 mmol) in phosphorus oxychloride (100 mL) was refluxed for 5 hours. The reaction was cooled to room temperature, and most of phosphorus oxychloride was removed under reduced pressure. The residue was dropwise added to ice water (500 mL), and the resulting precipitate was collected by the filtration to give the title compound (9 g, 87percent) as a yellow solid. MS (ES+) CStep 4: Synthesis of 6-bromo-2-chloroquinazoline. A solution of 6-bromoquinazolin-2-ol (31) (6.0 g, 26.7 mmol) in POC13 (80 mL) wasrefluxed at 110°C for 5 hours. An aliquot of the reaction mixture was analyzed by LCMS and indicated that the reaction had proceeded to completion. Most of POC13 was removed underreduced pressure, and the residue was added dropwise to ice water (500 mL). The resulting precipitate was collected via filtration as a yellow solid (3.5 g, 54percent). MS (ES+) C8H4BrC1N2 requires: 242, found: 243, 245 [M + H].A solution of 6-bromoquinazolin-2-ol (31) (6.0 g, 26.7 mmol) in POClA solution of 6-bromoquinazolin-2-ol (31) (6.0 g, 26.7 mmol) in POCl6 -Bromo-2-chloroquinazoline (300 mg, 1.2 mmol), azetidine HC1 salt (173 mg, 1.85 mmol), triethylamine (1.72 mL, 12.3 mmol) and l, 4-dioxane (10 mL) were added to the 25 mL microwave vial. The reaction mixture was heated in microwave reactor at l20C for 40 minutes. By LCMS targeted molecule was formed while some unreacted starting material was still remaining (the ratio between targeted molecule and starting material is about 2: 1 by LCMS). The reaction mixture was concentrated and purified on silica using ethyl acetate and hexanes. 2-(Azetidin-l-yl)-6-bromoquinazoline was obtained in 14% yield. 1H NMR (400 MHz, Chloroform-d): d 8.87 (s, 1H), 7.75 (d, J= 2.3 Hz, 1H), 7.67 (dd, J= 9.1, 2.3 Hz, 1H), 7.44 (d, J= 9.0 Hz, 1H), 4.24 (t, J= 7.5 Hz, 4H), 2.40 (p, J= 7.5 Hz, 2H) ppm.To a solution of
Computed Properties
Molecular Weight:243.49
XLogP3:3.2
Hydrogen Bond Acceptor Count:2
Exact Mass:241.92464
Monoisotopic Mass:241.92464
Topological Polar Surface Area:25.8
Heavy Atom Count:12
Complexity:167
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
