2,4-Dichloro-6-methoxyquinazoline

2,4-Dichloro-6-methoxyquinazoline Property

Melting point:

171 °C

Boiling point:

315.9±24.0 °C(Predicted)

Density 

1.450

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

-0.67±0.30(Predicted)

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C9H6Cl2N2O/c1-14-5-2-3-7-6(4-5)8(10)13-9(11)12-7/h2-4H,1H3

InChIKey

WEAMQTSRMCCGSJ-UHFFFAOYSA-N

SMILES

N1=C2C(C=C(OC)C=C2)=C(Cl)N=C1Cl

Safety

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN2811

HazardClass 

IRRITANT

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

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

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

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

2,4-Dichloro-6-methoxyquinazoline Chemical Properties,Usage,Production

Synthesis

Method F1: Synthesis of 2,4-dichloro-6-methoxyquinazoline (xa) To a mixture of 6-methoxyquinazoline-2,4(1H,3H)-dione (9.63 g, 50.2 mmol) and phosphorus trichloride (POCl3, 150 mL) was added N,N-dimethylaniline (0.5 mL). The reaction mixture was stirred at 120 °C for 2 hours. Upon completion of the reaction, the excess POCl3 was removed by distillation under reduced pressure. the residue was slowly poured into ice water and the pH was adjusted to about 7 by slowly adding saturated sodium bicarbonate (NaHCO3) solution at 0 °C, where a precipitate was formed. The precipitate was collected and dried under vacuum to give 2,4-dichloro-6-methoxyquinazoline (11.2 g, 98% yield) as a brown solid. LCMS m/z = 229.1, 231.0 [M + 1] (Method B) (retention time = 1.87 min). 1H-NMR (400 MHz, DMSO-d6): δ 7.89 (d, J = 9.2 Hz, 1H), 7.71 (dd, J = 8.8, 2.4 Hz, 1H), 7.38 (d, J = 1.6 Hz, 1H), 3.91 (s, 3H).

References

[1] Patent: US2015/307477, 2015, A1. Location in patent: Paragraph 1497
[2] Patent: JP6121658, 2017, B2. Location in patent: Paragraph 1096; 1099
[3] Patent: US2010/68197, 2010, A1. Location in patent: Page/Page column 17
[4] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 11, p. 2439 - 2444
[5] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 24, p. 7717 - 7727