6,7-Bis-(2-methoxyethoxy)-4(3H)-quinazolinone Chemical Properties

Melting point:

185-189°C

Boiling point:

467.8±55.0 °C(Predicted)

Density 

1.26±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO: ≥10mg/mL

pka

1.35±0.20(Predicted)

form 

powder

color 

off-white to light tan

InChI

InChI=1S/C14H18N2O5/c1-18-3-5-20-12-7-10-11(15-9-16-14(10)17)8-13(12)21-6-4-19-2/h7-9H,3-6H2,1-2H3,(H,15,16,17)

InChIKey

PMQWTUWLIGJTQD-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

179688-29-0(CAS DataBase Reference)

Safety Information

WGK Germany 

3

HS Code 

2933.59.8000

6,7-Bis-(2-methoxyethoxy)-4(3H)-quinazolinone Usage And Synthesis

Chemical Properties

Off-White Solid

Uses

An intermediate in the synthesis of Erlotinib (E625000).

Biological Activity

CP-380736 is an inhibitor of the epidermal growth factor receptor (EGFR). EGFR is a tyrosine kinase th at activates MAPK, JNK, and Akt pathways, and is an important mediator of several types of cancer, including lung cancer and glioblastoma multiforme.

Synthesis

GENERAL METHODS: To a solution of 6,7-dimethoxyquinazoline (200.0 mg, 1.05 mmol) in anhydrous ethanol (20 mL) was sequentially added 40% peracetic acid (1.0 mL, 5.26 mmol) and concentrated sulfuric acid (0.01 mL, 1.8 mmol). The reaction mixture was stirred in an oil bath at 60 °C for 4-12 h (the progress of the reaction was monitored by TLC). Upon completion of the reaction, the system was cooled to room temperature and residual peroxides were quenched by the addition of excess sodium bisulfite (541.8 mg, 5.26 mmol). After continued stirring for 20 min, the insoluble material was removed by filtration and the filtrate was concentrated under reduced pressure to give the crude product. The crude product was washed with a solvent mixture of ethanol and petroleum ether (1:1, v/v) to afford 6,7-dimethoxyethoxyquinazolin-4-one (179.7 mg, 83% yield) as a light yellow solid with a melting point of >300°C. The crude product was washed with a solvent mixture of ethanol and petroleum ether (1:1, v/v) to afford 6,7-dimethoxyethoxyquinazolin-4-one as a light yellow solid.

References

[1] Synthetic Communications, 2014, vol. 44, # 3, p. 346 - 351
[2] Tetrahedron, 2010, vol. 66, # 4, p. 962 - 968

6,7-Bis-(2-methoxyethoxy)-4(3H)-quinazolinone(179688-29-0)Related Product Information

• Cefazolin sodium salt
• Quinoxaline
• Cefazolin
• 2-Amino-4,5-bis(2-methoxyethoxy)benzoic acid ethyl ester hydrochloride
• 3-Ethynylaniline
• Erlotinib hydrochloride
• 4-Chloro-6,7-bis(2-methoxyethoxy)quinazoline
• N-[3-Chloro-4-(3-fluorobenzyloxy)phenyl]-6-iodoquinazolin-4-amine
• Ethyl 3,4-dihydroxybenzoate
• 4-Quinazolinamine,N-(3-ethenylphenyl)-6,7-bis(2-methoxyethoxy)-,hydrochloride(1:1)
• Erlotinib Impurity 20
• Erlotinib Impurity 1
• Erlotinib Impurity 3
• DesMethyl Erlotinib Carboxylate Acid
• Erlotinib Impurity 35
• 4-CHLORO-7-(2-CHLORO-ETHOXY)-6-(2-METHOXY-ETHOXY)-QUINAZOLINE
• Ethyl 3,4-bis(2-methoxyethoxy)benzoate
• Erlotinib Hydrochloride iMpurity