J IRAN CHEM SOC
4-(4-chlorophenyl)-6-(4-methoxyphenyl)-2-(piperidin-
(dppm): 2.90 (s, 6H, 2CH3), 3.40 (br, s, 1H, –NH), 5.16 (d,
J = 3.5 Hz, 1H, =CH), 5.21 (s, 2H, CH2), 5.23 (s, 1H,
CH), 7.36–7.90 (m, 10H, Ar–H); EI-MS: 307(M?); Anal.
Calcd. For C19H21N3O: C, 74.73; H, 6.27; N, 13.76. Found:
C,74.71; H,6.24; N,13.70 %.
1-ylmethoxy)-1,6-dihydropyrimidine (5 h)
Yield 84 %, mp 148–150 °C; IR (KBr) cm-1: 3,241, 3,058,
2,896, 1,659, 1,601, 1,475, 1,251, 1,092, 760; H NMR
1
(dppm): 2.19–2.49 (m, 10H, 5CH2), 3.47 (br, s, 1H, –NH),
3.76 (s, 3H, OCH3), 5.13 (s, 2H, CH2), 5.14 (d, J = 3.1 Hz,
1H, =CH), 5.22 (s, 1H, CH), 7.25–7.96 (m, 8H, Ar–H); EI-
MS: 411(M?); Anal. Calcd. For C23H26ClN3O2: C, 67.39;
H, 5.90; N, 10.25. Found: C,67.35; H,5.88; N,10.23 %.
4-(((4,6-bis(4-chlorophenyl)-1,6-dihydropyrimidin-2-
yl)oxy)methyl)morpholine (5d)
Yield 65 %, mp 146–149 °C; IR (KBr) cm-1: 3,254,
3,062, 2,860, 1,660, 1,596, 1,475, 1,250, 1,090, 750; H
1
1-((4-(4-chlorophenyl)-6-(4-methoxyphenyl)-1,6-
dihydropyrimidin-2-yl)oxy)-N,N-dimethylmethanamine
(5i)
NMR (dppm): 2.87 (t, 4H, 2CH2), 3.41 (br, s, 1H, –NH),
3.54 (t, 4H, 2CH2), 4.70 (s, 2H, CH2), 5.18 (d, J = 4.2 Hz,
1H, =CH), 5.22 (s, 1H, CH), 7.31–8.10 (m, 8H, Ar–H); EI-
MS: 417(M?); Anal. Calcd. For C21H21Cl2N3O2: C, 60.59;
H, 4.60; N, 10.09. Found: C, 60.57; H, 4.58; N, 10.07 %.
Yield 68 %, mp 169–172 °C; IR (KBr) cm-1: 3,246,
3,052, 2,895, 1,658, 1,604, 1,476, 1,255, 1,090, 765; H
1
NMR (dppm): 2.91 (s, 6H, 2CH3), 3.44 (br, s, 1H, –NH),
3.75 (s, 3H, OCH3), 5.01 (s, 2H, CH2), 5.16 (d, J = 4.2 Hz,
1H, =CH), 5.23 (s, 1H, CH), 7.30–8.00 (m, 8H, Ar–H); EI-
MS: 371(M?); Anal. Calcd. For C20H22ClN3O2: C, 64.95;
H, 5.45; N, 11.36. Found: C,64.91; H,5.43; N,10.32 %.
4,6-bis(4-chlorophenyl)-2-(piperidin-1-ylmethoxy)-1,6-
dihydropyrimidine (5e)
Yield 76 %, mp 163–166 °C; IR (KBr) cm-1: 3,248,
3,055, 2,900, 1,666, 1,596, 1,476, 1,252, 1,092, 755; H
1
4-(((6-(4-methoxyphenyl)-4-(3-nitrophenyl)-1,6-
dihydropyrimidin-2-yl)oxy)methyl)morpholine (5j)
NMR (dppm): 2.19–2.49 (m, 10H, 5CH2), 3.39 (br, s, 1H,
–NH), 5.01 (s, 2H, CH2), 5.16 (d, J = 3.0 Hz, 1H, =CH),
5.20 (s, 1H, CH), 7.34–8.10 (m, 8H, Ar–H); EI-MS:
415(M?); Anal. Calcd. For C22H23Cl2N3O: C, 63.77; H,
5.11; N, 10.14. Found: C,63.71; H,5.12; N,10.10 %.
Yield 73 %, mp 192–194 °C; IR (KBr) cm-1: 3,254,
3,058, 2,901, 1,658, 1,596, 1,525, 1,470, 1,350, 1,250,
1
1,090; H NMR (dppm): 2.97 (t, 4H, 2CH2), 3.43 (br, s,
1H, –NH), 3.69 (t, 4H, 2CH2), 3.83 (s, 3H, OCH3), 5.01 (s,
2H, CH2), 5.18 (d, J = 3.4 Hz, 1H, =CH), 5.22(s, 1H, CH)
7.25–8.06 (m, 8H, Ar–H); EI-MS: 424(M?); Anal. Calcd.
For C22H24N4O5: C, 62.55; H, 5.25; N, 13.26. Found:
C,62.52; H,5.22; N,13.22 %.
1-((4,6-bis(4-chlorophenyl)-1,6-dihydropyrimidin-2-
yl)oxy)-N,N-dimethylmethanamine (5f)
Yield 73 %, mp 144–148 °C; IR (KBr) cm-1: 3,256,
3,057, 2,850, 1,658, 1,596, 1,478, 1,257, 1,094, 750; H
1
6-(4-methoxyphenyl)-4-(3-nitrophenyl)-2-(piperidin-1-
ylmethoxy)-1,6-dihydropyrimidine (5 k)
NMR (dppm): 2.87 (s, 6H, 2CH3), 3.42 (br, s, 1H, –NH),
5.01(s, 2H, CH2), 5.19 (d, J = 2.6 Hz, 1H, =CH), 5.21 (s,
1H, CH), 7.34–8.10 (m, 8H, Ar–H); EI-MS: 375(M?);
Anal. Calcd. For C19H19Cl2N3O: C, 60.97; H, 4.58; N,
11.23. Found: C,60.91; H,4.52; N,11.21 %.
Yield 77 %, mp 181–184 °C; IR (KBr) cm-1: 3,241,
3,054, 2,905, 1,652, 1,601, 1,522, 1,472, 1,348, 1,252,
1
1,091; H NMR (dppm): 2.19–2.49 (m, 10H, 5CH2), 3.47
(br, s, 1H, –NH), 3.76 (s, 3H, OCH3), 5.01 (s, 2H, CH2),
5.19 (d, J = 3.9 Hz, 1H, =CH), 5.21 (s, 1H, CH),
7.30–8.00 (m, 8H, Ar–H); EI-MS: 422(M?); Anal. Calcd.
For C23H26N4O4: C, 68.70; H, 5.75; N, 13.33. Found:
C,68.68; H,5.72; N,13.30 %.
4-(((4-(4-chlorophenyl)-6-(4-methoxyphenyl)-1,6-
dihydropyrimidin-2-yl)oxy)methyl)morpholine (5 g)
Yield 76 %, mp 168–170 °C; IR (KBr) cm-1: 3,245,
3,055, 2,905, 1,654, 1,596, 1,475, 1,259, 1,090, 756; H
1
NMR (dppm): 2.97 (t, 4H, 2CH2), 3.47 (br, s, 1H, –NH),
3.69 (t, 4H, 2CH2), 3.76 (s. 3H, OCH3), 5.13 (s, 2H, CH2),
5.16 (d, J = 4.0 Hz, 1H, =CH), 5.23(s, 1H, CH) 7.25–8.06
(m, 8H, Ar–H); EI-MS: 413(M?); Anal. Calcd. For C22-
H24ClN3O3: C, 64.15; H, 5.38; N, 10.21. Found: C,64.12;
H,5.35; N,10.19 %.
1-((6-(4-methoxyphenyl)-4-(3-nitrophenyl)-1,6-
dihydropyrimidin-2-yl)oxy)-N,N-dimethylmethanamine
(5 l)
Yield 64 %, mp 167–170 °C; IR (KBr) cm-1: 3,252,
3,052, 2,908, 1,658, 1,596, 1,525, 1,478, 1,350, 1,258,
123