4176
Molecules 2009, 14
(E)-3-(4-ethoxy-3-methoxyphenyl)-N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino]phenyl]acryla-
1
mide (12s): yield: 68.8%; mp: 256-258 ºC. H-NMR δ: 10.03 (s, 1H, NHCO), 9.26 (d, 1H, J = 1.8,
Py-2-H), 8.92 (s, 1H, NH), 8.68 (dd, 1H, J1 = 4.8, J2 = 1.6, Py-6-H), 8.51(d, 1H, J = 5.2,
pyrimidinyl-6-H), 8.47 (dt, 1H, J1 = 8.1, J2 = 1.9 Py-4-H), 7.97 (d, 1H, J = 1.9), 7.53 (dd, 1H, J1 = 8.0,
J2 = 4.8, Py-5-H), 7.50 (d, 1H, J = 15.6,COCH=CH), 7.42 (d,1H, J = 5.1), 7.40 (d, 1H, J = 2.0), 7.20 (d,
1H, J = 1.9), 7.18 (d, 1H, J = 8.4), 7.15 (dd, 1H, J1 = 8.4, J2 = 1.9), 6.99 (d, 1H, J = 8.4), 6.70 (d, 1H, J
= 15.7, COCH=CH ), 4.05 (q, 2H, J = 7.0, OCH2CH3), 3.81 (s, 3H, OCH3), 2.22 (s, 3H, CH3), 1.34 (t,
3H, J = 7.0, OCH2CH3); HRMS m/z calcd. for C28H28N5O3 [M+H]+ 482.21921, found: 482.22009.
(E)-3-(3-ethoxy-4-methoxyphenyl)-N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)phenyl]acryla-
1
mide (12t): yield: 68.5%; mp: 263-264 ºC. H-NMR δ: 10.01 (s, 1H, NHC=O), 9.26 (d, 1H, J = 1.8,
Py-2-H), 8.92 (s, 1H, NH), 8.68 (dd, 1H, J1 = 4.8, J2 = 1.6, Py-6-H), 8.51 (d, 1H, J = 5.2, pyrimidinyl
-6-H), 8.47 (dt, 1H, J1 = 8.1, J2 = 1.9, Py-4-H), 7.97 (d, 1H, J = 1.9), 7.53 (dd, 1H, J1 = 8.0, J2 = 4.8,
Py-5-H), 7.50 (d, 1H, J = 15.6, COCH=CH)), 7.42 (d,1H, J = 5.1), 7.40 (d, 1H, J = 2.1), 7.19-7.16 (m,
3H), 7.00 (d,1H, J = 8.4), 6.70 (d, 1H, J = 15.7, COCH=CH), 4.06(q, 2H, J = 6.9, OCH2CH3) 3.80 (s,
3H, OCH3), 2.21 (s, 3H, CH3), 1.35 (t, 3H, J = 6.9, OCH2CH3); HRMS m/z calcd. for C28H28N5O3
[M+H]+ 482.21921, Found: 482.22036.
(E)-3-(4-benzyloxy-3-methoxyphenyl)-N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)phenyl]
1
acrylamide (12u): yield: 36.4%; mp: 178-179 ºC. H-NMR δ: 10.08 ( s, 1H, NHCO), 9.27 (d, 1H J =
1.8, Py-2-H), 8.98 (s, 1H, NH), 8.69 (dd, 1H, J1= 4.8, J2 = 1.6, Py-6-H ), 8.51 (d, 1H, J = 5.1,
pyrimidinyl-6-H), 8.46 (dt, 1H, J1 = 8.1, J2 = 1.9, Py-4-H), 7.97 (d, 1H, J = 1.7), 7.53 (dd, 1H, J1 = 8.0,
J2 = 4.8, Py-5-H), 7.51 (1H, J = 15.7, COCH=CH), 7.49-7.47 (m, 2H), 7.44-7.40 (m, 4H), 7.36-7.33
(m, 1H), 7.33 (d, 1H, J = 1.6), 7.22 (dd, 1H, J1 = 8.4, J2 = 1.8), 7.18 (d, 1H, J = 8.4), 7.05 (d, 1H, J =
8.7), 6.70 (d, 1H, J = 15.6, COCH=CH), 5.20 (s, 2H, OCH2Ph), 3.83 (s, 3H, OCH3), 2.20 (s, 3H,
CH3);HRMS m/z calcd. for C33H30N5O3 [M+H]+ 544.23486, found: 544.23565.
(E)-3-(3-benzyloxy-4-methoxyphenyl)-N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]
1
acrylamide (12v) yield: 42.7%; mp: 232-234 ºC. H-NMR δ: 10.04 ( s, 1H, NHCO), 9.27(d, 1H, J =
1.8, Py-2-H), 8.92( s,1 H, NH), 8.69 (dd, 1H, J1 = 4.8, J2 = 1.6, Py-6-H ), 8.51 (d, 1H, J = 5.1,
pyrimidinyl-6-H), 8.46 (dt, 1H, J1 = 8.1, J2 = 1.9, Py-4-H), 7.97 (d, 1H, J = 1.7), 7.53 (dd, 1H, J1 = 8.0,
J2 = 4.8, Py-5-H), 7.50 (d, 1H, J = 15.8, COCH=CH), 7.46-7.44 (m, 2H), 7.42-7.38 (m, 4H), 7.35-7.33
(m, 1H), 7.23 (d, 1H, J = 1.9), 7.18 (d, 1H, J = 8.4), 7.15 (dd, 1H, J1 = 8.4, J2 = 1.8),7.09 (d, 1H, J =
8.4), 6.70 (d, 1H, J = 15.6, COCH=CH), 5.13 (s, 2H, OCH2Ph), 3.83 (s, 3H, OCH3), 2.20 (s, 3H, CH3);
HRMS m/z calcd. for C33H30N5O3 [M+H]+ 544.23486, found: 544.23565.
(E)-3-benzo[1,3]dioxol-5-yl-N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)phenyl]acrylamide
(12w): yield: 46.8%; mp: 244-246 ºC. 1H-NMR δ: 10.02 (s, 1H, NHCO), 9.26 (d, 1H, J = 1.2, Py-2-H),
8.91 (s, 1H, NH), 8.69 (dd, 1H, J1 = 4.5, J2 = 1.1, Py-6-H), 8.51 (d, 1H, J =5.1, pyrimidinyl-6-H), 8.46
(dt, 1H, J1 = 8.1, J2 = 1.9, Py-4-H), 7.97 (d, 1H, J = 1.3), 7.53 (dd, 1H, J1 = 8.0, J2 = 4.8, Py-5-H), 7.49
(d, 1H, J=15.6, COCH=CH), 7.42 (d, 1H, J = 5.1), 7.40 (d, 1H, J = 1.6), 7.18 (d, 2H, J = 7.2), 7.13 (dd,