BULLETIN OF THE
Article
2-(2-Aminopyrimidin-4-yl)phenol as VEGFR-2 Kinase Inhibitor
KOREAN CHEMICAL SOCIETY
3-chloroperbenzoic acid and the mixture was stirred for
6 h. After addition of isopropyl alcohol, the mixture was stir-
red for 20 min. After removal of solvent, the residue was trea-
ted with DCM and DCM solution was washed several times
with saturated aqueous sodium bicarbonate and dried over
anhydrous MgSO4. The crude product was purified by column
chromatography (hexane/EA = 1/1, vol/vol) to give 82 mg in
m), 2.66–2.58 (2H, m), 2.55–2.47 (4H, m), 2.43 (3H, s).
FAB MS (m/e) = 452 [M + l].
(3-(2-Amino-6-((3-(4-methylpiperazin-1-yl)propyl)amino)
pyrimidin-4-yl)-4-hydroxyphenyl)(2-fluoro-4-methylphenyl)
l
methanone (23): H NMR (CDCl3, ppm); δ 8.36 (1H,
J =2.4 Hz, d), 7.64 (1H, J =8.8 Hz, 2.0 Hz, dt), 7.42
(1H, J = 6.2 Hz, t), 7.06 (1H, J = 6.4 Hz, d), 6.98 (1H,
J = 8.8 Hz, d), 6.92 (1H, J = 6.8 Hz, d), 6.27 (2H, s), 4.80
(2H, s), 3.51–3.39 (2H, m), 2.53–2.47 (10H, m), 2.43 (3H, s),
2.32 (3H, s). FAB MS (m/e) = 479 [M + l].
l
22 % yield. H NMR (CDCl3, ppm); δ 8.18 (1H, J = 2.4 Hz,
d), 8.02 (1H, J = 8.8 Hz, 2.0 Hz, dt), 7.54 (1H, s), 7.45 (1H,
J = 6.2 Hz, t), 7.43–7.31 (5H, m), 7.16 (1H, J = 8.8 Hz, d),
7.06 (1H, J = 8.0 Hz, d), 6.97 (1H, J = 10.8 Hz, d), 5.22 (2H,
s), 3.13 (3H, s), 2.42 (3H, s). FAB MS (m/e) =492 [M + l].
(3-(2-Amino-6-((3-morpholinopropyl)amino)pyrimi-
din-4-yl)-4-(benzyloxy)phenyl)(2-fluoro-4-methylphenyl)
methanone: To the 2 mL of acetonitrile solution of 30 mg
(0.061 mmol) of (3-(2-amino-6-(methylsulfonyl)pyrimidin-
4-yl)-4-(benzyloxy)phenyl)(2-fluoro-4-methylphenyl)metha-
none was added 0.18 mL of 4-(3-aminopropyl)morpholine
and the reaction mixture was refluxed for 8 h. After solvent
was removed, the residue was treated with EA and washed
with water. The crude product was purified by column
chromatography (chloroform/methanol/ammonium hydrox-
Acknowledgment. This research was supported by the
Bisa Research Grant (20130335) of Keimyung University
in 2013.
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Bull. Korean Chem. Soc. 2017, Vol. 38, 70–77
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