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Chemical Structure| 491-36-1 Chemical Structure| 491-36-1
Chemical Structure| 491-36-1

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CAS No.: 491-36-1

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4-HQN is a PARP inhibitor with IC50 of 9.5 μM.

Synonyms: 4(3H)-Quinazolinone; 4-HQN; 4-Quinazolinol

4.5 *For Research Use Only !

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Product Details of 4-Hydroxyquinazoline

CAS No. :491-36-1
Formula : C8H6N2O
M.W : 146.15
SMILES Code : OC1=C2C=CC=CC2=NC=N1
Synonyms :
4(3H)-Quinazolinone; 4-HQN; 4-Quinazolinol
MDL No. :MFCD00511302
InChI Key :QMNUDYFKZYBWQX-UHFFFAOYSA-N
Pubchem ID :135408753

Safety of 4-Hydroxyquinazoline

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 4-Hydroxyquinazoline

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 491-36-1 ]

[ 491-36-1 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 17641-08-6 ]
  • [ 491-36-1 ]
  • [ 108086-41-5 ]
  • 2
  • [ 491-36-1 ]
  • [ 1798-83-0 ]
  • [ 108664-81-9 ]
  • 3
  • [ 273-34-7 ]
  • [ 491-36-1 ]
  • [ 1147704-33-3 ]
YieldReaction ConditionsOperation in experiment
30% Example 104 4-(3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)quinazoline To a solution of a hydroxyquinazoline (400 mg, 2.73 mmol), and BOP (1450 mg, 3.2 mmol) was added DBU (0.61 mL, 4.09 mmol) at room temperature under nitrogen. The resultant mixture was stirred for 5-10 min at room temperature, after which 3H-[1,2,3 <strong>[273-34-7]triazolo[4,5-b]pyridine</strong> (714 mg, 6.0 mmol) was added. The reaction mixture was monitored by LCMS till complete consumption of starting material (30 hrs). The solvent was removed under vacuum, the crude reaction mixture was purified by a flash chromatography on SiO2 column eluted with hexanes/EtOAc to give the desired product (200 mg, 30%). 1H-NMR (CDCl3, 400 MHz) delta (ppm) 9.43 (s, 1H), 9.01 (d, 1H, J=8.4 Hz), 8.93 (m, 2H), 8.22-8.19 (m, 2H), 7.99-7.96 (m, 1H), 7.87 (dd, 1H, J=8.0 Hz, J=4.4 Hz).
  • 4
  • [ 13959-34-7 ]
  • [ 491-36-1 ]
  • 3-(2-(4-methylpyridin-2-yl)ethyl)quinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With scandium tris(trifluoromethanesulfonate); In toluene; at 110℃; for 12.0h;Inert atmosphere; General procedure: Typically, quinazolinone (0.5 mmol, 73.0 mg), 2-vinylpyridine (1.0 mmol, 105.0 mg), Sc(OTf)3 (0.05 mmol, 24.6 mg) were charged sequentially into the flask with 3 mL toluene. The flask was then evacuated under reduced pressure, followed by the attachment of a nitrogen balloon. The resulting mixture was stirred at 110 for 12 h. The progress of the reaction was monitored by TLC. After the reaction was completed, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel (EA/MeOH = 250:1 150:1) to give the product 3a (103 mg, 82 %) as a white solid. 3-(2-(pyridin-2-yl)ethyl)quinazolin-4(3H)-one (3a). The title compound was prepared according to the general procedure as described above in 82 % yield as white powder, 103 mg.
  • 5
  • [ 3883-39-4 ]
  • [ 491-36-1 ]
  • 3-(2-(5-methylpyridin-2-yl)ethyl)quinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With scandium tris(trifluoromethanesulfonate); In toluene; at 110℃; for 12.0h;Inert atmosphere; General procedure: Typically, quinazolinone (0.5 mmol, 73.0 mg), 2-vinylpyridine (1.0 mmol, 105.0 mg), Sc(OTf)3 (0.05 mmol, 24.6 mg) were charged sequentially into the flask with 3 mL toluene. The flask was then evacuated under reduced pressure, followed by the attachment of a nitrogen balloon. The resulting mixture was stirred at 110 for 12 h. The progress of the reaction was monitored by TLC. After the reaction was completed, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel (EA/MeOH = 250:1 150:1) to give the product 3a (103 mg, 82 %) as a white solid. 3-(2-(pyridin-2-yl)ethyl)quinazolin-4(3H)-one (3a). The title compound was prepared according to the general procedure as described above in 82 % yield as white powder, 103 mg.
  • 6
  • [ 13959-34-7 ]
  • [ 491-36-1 ]
  • 3-(2-(4-methylpyridin-2-yl)ethyl)quinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With scandium tris(trifluoromethanesulfonate); In toluene; at 110℃;Inert atmosphere; 4-Hydroxyquinazoline (1mmol), <strong>[13959-34-7]4-methyl-2-vinylpyridine</strong> (1.5mmol), scandium trifluoromethanesulfonate (0.1mmol) were added to a single-necked flask containing 4mL of toluene, and the flask The air was replaced with argon, and then stirred at 110C. The reaction process was monitored by thin layer chromatography. After the reaction was completed, it was quenched with water (15 mL). The reaction product was extracted with methylene chloride (3×20 mL), washed with saturated brine (20 mL), dehydrated with anhydrous Na 2 SO 4, filtered, and the resulting filtrate was concentrated and passed through a silica gel column (300-400 mesh, the developing agent was ethyl acetate/ Methanol = 450:1) chromatographic separation to obtain product 209.6mg, yield 79%.
 

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