6-METHOXY-7-HYDROXYQUINAZOLIN-4-ONE

6-METHOXY-7-HYDROXYQUINAZOLIN-4-ONE Property

Melting point:

>255oC (dec.)

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, Heated), Methanol (Slightly, Heated)

pka

8.07±0.20(Predicted)

form 

Solid

color 

Light Beige

InChI

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

InChIKey

ZHLRYPLSYOYNQM-UHFFFAOYSA-N

SMILES

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

Safety

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

6-METHOXY-7-HYDROXYQUINAZOLIN-4-ONE Chemical Properties,Usage,Production

Uses

7-Hydroxy-6-methoxy-3,4-dihydroquinazolin-4-one is a potential 2-arylbenzothiazoles based kinase inhibitor.

Synthesis

General procedure for the synthesis of 6-methoxy-7-(benzyloxy)quinazolin-4(3H)-one from 6-methoxy-7-hydroxyquinazolin-4-one: Compound 122 (247 g, 875.6 mmol) was dissolved in trifluoroacetic acid (800 mL), followed by a one-time addition of methanesulfonic acid (127 mL). The reaction mixture was heated to reflux and maintained for 3 hours. Upon completion of the reaction, the mixture was cooled to room temperature and concentrated. To the concentrated mixture, 2.5 N of aqueous sodium hydroxide was added and the pH of the solution was adjusted to 7, at which point precipitation was observed to be generated. The resulting solid was pulverized and subjected to vigorous stirring for 1 hour followed by filtration operation. The solid product was collected and dried under high vacuum to give the final compound 123 (148 g, yield = 88%) presenting as a brown solid.

References

[1] Tetrahedron Letters, 2005, vol. 46, # 43, p. 7381 - 7384
[2] Patent: US2014/235634, 2014, A1. Location in patent: Paragraph 0390; 0395
[3] Patent: WO2004/94410, 2004, A1. Location in patent: Page 122
[4] Patent: WO2004/113324, 2004, A1. Location in patent: Page 52
[5] Patent: WO2005/13998, 2005, A1. Location in patent: Page/Page column 60