6-Hydroxy-7-methoxy-3,4-dihydroquinazolin-4-one Chemical Properties

Melting point:

293 °C

Boiling point:

420.0±55.0 °C(Predicted)

Density 

1.47±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

powder to crystal

pka

9.39±0.20(Predicted)

color 

White to Almost white

InChI

InChI=1S/C9H8N2O3/c1-14-8-3-6-5(2-7(8)12)9(13)11-4-10-6/h2-4,12H,1H3,(H,10,11,13)

InChIKey

OKZIRNNFVQCDSA-UHFFFAOYSA-N

SMILES

N1C2=C(C=C(O)C(OC)=C2)C(=O)NC=1

CAS DataBase Reference

179688-52-9(CAS DataBase Reference)

Safety Information

HS Code 

2933998090

6-Hydroxy-7-methoxy-3,4-dihydroquinazolin-4-one Usage And Synthesis

Chemical Properties

White powder

Uses

6-Hydroxy-7-methoxy-4(1H)-quinazolinone is a reactant used in the preparation of 4-anilinoquinazoline derivatives that have shown antitumor activities. 6-Hydroxy-7-methoxy-4(1H)-quinazolinone was also used as a reactant in the synthetic preparation of 2-arylbenzothiazoles as kinase inhibitors.

Synthesis

General procedure for the synthesis of 6-hydroxy-7-methoxyquinazolin-4-one from 6,7-dimethoxyquinazolin-4-one: 1. 3.06 g of 6,7-dimethoxyquinazolin-4-one was dissolved in 20 mL of methanesulfonic acid. 2. 2.66 g of L-methionine was added to the above solution and the reaction was stirred at 100 °C for 22 hours. 3. Upon completion of the reaction, ice was added to the reaction mixture and neutralized with 40% aqueous sodium hydroxide solution to pH neutral to promote crystallization of the product. 4. The solid product was collected by filtration under reduced pressure, washed with water and subsequently air dried to afford 6-hydroxy-7-methoxyquinazolin-4-one (2.67 g, 94% yield). Product characterization data: 1H-NMR (300MHz, DMSO-d6) δ 11.94 (s, 1H), 9.81 (s, 1H), 7.92 (d, J=Hz, 1H), 7.39 (s, 1H), 7.11 (s, 1H), 3.91 (s, 3H).

References

[1] European Journal of Medicinal Chemistry, 2009, vol. 44, # 7, p. 3046 - 3055
[2] Patent: WO2008/150118, 2008, A2. Location in patent: Page/Page column 21
[3] Patent: WO2005/97134, 2005, A2. Location in patent: Page/Page column 13; figure 1
[4] Angewandte Chemie - International Edition, 2013, vol. 52, # 33, p. 8551 - 8556
[5] Angew. Chem., 2013, vol. 125, # 33, p. 8713 - 8718,6

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