4-CHLORO-5-FLUOROQUINAZOLINE Chemical Properties

Boiling point:

284.9±20.0 °C(Predicted)

Density 

1.447±0.06 g/cm3(Predicted)

storage temp. 

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

pka

0.35±0.30(Predicted)

Appearance

White to off-white Solid

4-CHLORO-5-FLUOROQUINAZOLINE Usage And Synthesis

Synthesis

The general procedure for the synthesis of 4-chloro-5-fluoroquinazoline from 5-fluoroquinazolin-4(1H)-one was as follows: a DCM ( 197 mg) of HATU (197 mg), diisopropylethylamine (90 μL), acetic acid (22 μL), and N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[2-(methylamino)ethoxy]quinazolin-4-amine (150 mg) ( 20 mL) solution was stirred for 2 hours. After completion of the reaction, the reaction solution was washed with water, then with brine and finally concentrated in vacuum. The residue was purified by column chromatography using DCM-5% methanol as eluent to give the title compound as a white solid (114 mg, 69% yield).NMR spectrum (DMSO-d6) δ 1.95 (s, 3H), 3.00 (s, 3H), 3.89 (t, 2H), 4.48 (m, 2H), 5.29 (s, 2H), 7.18 ( d, 1H), 7.24 (d, 1H), 7.35 (m, 2H), 7.59 (m, 2H), 7.72 (dd, 1H), 7.85 (dt, 1H), 7.96 (d, 1H), 8.46 (s, 1H), 8.58 (m, 1H), 9.70 (bs, 1H); mass spectrum m/z 478 [M+H]+.

References

[1] Patent: WO2005/51923, 2005, A1. Location in patent: Page/Page column 158-159
[2] Patent: WO2004/93880, 2004, A1. Location in patent: Page/Page column 83
[3] Patent: WO2005/26152, 2005, A1. Location in patent: Page/Page column 118
[4] Patent: WO2006/92573, 2006, A1. Location in patent: Page/Page column 64
[5] Patent: WO2007/34144, 2007, A1. Location in patent: Page/Page column 75

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