S. Linz et al. / Bioorg. Med. Chem. 17 (2009) 4448–4458
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4.2.10. 3-{[4-(3,4-Dichlorophenyl)piperazin-1-yl]methyl}-2,7-
dimethylimidazo[1,2-c]pyrimidine (28c)
3.13 (m, 4H, 2 ꢁ NCH2CH2), 3.19 (s, 3H, Me-5), 3.81 (s, 2H, ArCH2N),
6.71 (dd, 1H, H-60, J1 = 3.0 u. J2 = 8.7 Hz), 6.93 (d, 1H, H-20,
J = 3.0 Hz), 7.16 (s, 1H, H-8), 7.26 (d, 1H, H-50, J = 8.7 Hz), 7.41 (s,
1H, H-2); MS, m/z = 393 (M+); 391 (M+), 389 (M+); Anal.
(C19H21Cl2N5) C, H, N.
This compound, a vanilla-coloured powder, was obtained in a
yield of 0.23 g (45%). Mp 204–205 °C; IR 2920, 2827, 1630,
1141 cmꢀ1 1H NMR (CDCl3) d: 2.53 (s, 3H, Me-2), 2.56 (s, 3H,
;
Me-7), 2.67 (m, 4H, 2 ꢁ NCH2CH2), 3.18 (m, 4H, 2 ꢁ NCH2CH2),
3.72 (s, 2H, ArCH2N), 6.70 (dd, 1H, H-60, J1 = 2.7 u. J2 = 8.8 Hz),
6.92 (d, 1H, H-20, J = 2.7 Hz), 7.23 (s, 1H, H-8), 7.24 (d, 1H, H-50,
J = 8.8 Hz), 8.70 (s, 1H, H-5); MS, m/z = 393 (M+), 391 (M+), 389
(M+); Anal. (C19H21Cl2N5) C, H, N.
4.2.17. 3-{[4-(2-Methoxyphenyl)piperazin-1-yl]methyl}-5,7-
dimethylimidazo[1,2-c]pyrimidine (29d)
This compound was made up in yields of 0.19 g (41%) as a light
yellow powder. Mp 173–174 °C; IR 2937, 2817, 1631, 1240 cmꢀ1
;
1H NMR (CDCl3) d: 2.51 (s, 3H, Me-7), 2.82 (m, 4H, 2 ꢁ NCH2CH2),
3.13 (m, 4H, 2 ꢁ NCH2CH2), 3.30 (s, 3H, Me-5), 3.87 (s, 2H, ArCH2N),
3.91 (s, 3H, 20-OMe), 6.83–7.06 (m, 4H, H-30-. H-60), 7.22 (s, 1H, H-
8), 7.56 (s, 1H, H-2); MS, m/z = 351 (M+); Anal. (C20H25N5O) C, H, N.
4.2.11. 3-{[4-(2-Methoxyphenyl)piperazin-1-yl]methyl}-2,7-
dimethylimidazo[1,2-c]pyrimidine (28d)
This compound was obtained as a light yellow powder in yields
of 0.21 g (46%). Mp 194–195 °C; IR 2924, 2816, 1630, 1240 cmꢀ1
;
1H NMR (CDCl3) d: 2.40 (s, 3H, Me-2), 2.55 (s, 3H, Me-7), 2.68
(m, 4H, 2 ꢁ NCH2CH2), 3.09 (m, 4H, 2 ꢁ NCH2CH2), 3.83 (s, 3H, O-
Me), 3.83 (s, 2H, ArCH2N), 6.78 – 7.01 (m, 4H, H-30 - H-60), 7.20
(s, 1H, H-8), 9.12 (s, 1H, H-5); MS, m/z = 351 (M+); Anal.
(C20H25N5O) C, H, N.
4.2.18. 3-{[4-(4-Methoxyphenyl)piperazin-1-yl]methyl}-5,7-
dimethylimidazo[1,2-c]pyrimidine (29e)
This compound was obtained as a pale yellow powder in a yield
of 0.18 g (39%). Mp 163–164 °C; IR 2954, 1631, 1241 cmꢀ1 1H
;
NMR (CDCl3) d: 2.52 (s, 3H, Me-7), 2.65 (m, 4H, 2 ꢁ NCH2CH2),
3.09 (m, 4H, 2 ꢁ NCH2CH2), 3.24 (s, 3H, Me-5), 3.80 (s, 3H, O-
Me), 3.86 (s, 2H, ArCH2N), 6.81–7.02 (m, 4H, H-20, H-30, H-50 u.
H-60), 7.19 (s, 1H, H-8), 7.44 (s, 1H, H-2); MS, m/z = 351 (M+); Anal.
(C20H25N5O) C, H, N.
4.2.12. 3-{[4-(4-Methoxyphenyl)piperazin-1-yl]methyl}-2,7-
dimethylimidazo[1,2-c]pyrimidine (28e)
This compound was obtained as a pale yellow powder in a yield
of 0.17 (37%). Mp 152–153 °C; IR 2947, 1629, 1242 cmꢀ1 1H NMR
;
(CDCl3) d: 2.40 (s, 3H, Me-2), 2.55 (s, 3H, Me-7), 2.66 (m, 4H,
2 ꢁ NCH2CH2), 3.06 (m, 4H, 2 ꢁ NCH2CH2), 3.87 (s, 3H, O-Me),
3.87 (s, 2H, ArCH2N), 6.83–7.04 (m, 4H, H-20, H-30, H-50 u. H-60),
7.20 (s, 1H, H-8), 9.20 (s, 1H, H-5); MS, m/z = 351 (M+); Anal.
(C20H25N5O) C, H, N.
4.2.19. 5,7-Dimethyl-3-[(4-pyridin-2-ylpiperazin-1-yl)methyl]
imidazo[1,2-c]pyrimidine (29f)
This derivative, a vanilla-coloured powder, was obtained in
yields of 0.17 g (41%). Mp 169–170 °C; IR 2921, 2819, 1631 cmꢀ1
;
1H NMR (CDCl3) d: 2.47 (s, 3H, Me-7), 2.56 (m, 4H, 2 ꢁ NCH2CH2),
3.21 (s, 3H, Me-5), 3.51 (m, 4H, 2 ꢁ NCH2CH2), 3.80 (s, 2H, ArCH2N),
6.62 (m, 2H, H-40 u. H-60), 7.16 (s, 1H, H-8), 7.40 (s, 1H, H-2), 7.46
(m, 1H, H-50), 8.17 (m, 1H, H-30); MS, m/z = 322 (M+); Anal.
(C18H22N6) C, H, N.
4.2.13. 2,7-Dimethyl-3-[(4-pyridin-2-ylpiperazin-1-yl]methyl}
imidazo[1,2-c]pyrimidine (28f)
This compound was obtained as a pale yellow powder in a yield
of 0.17 g (40%). Mp 211–212 °C; IR 3033, 2943, 1630 cmꢀ1; 1H NMR
(CDCl3) d: 2.42 (s, 3H, Me-2), 2.53 (s, 3H, Me-7), 2.56 (m, 4H,
2 ꢁ NCH2CH2), 3.51 (m, 4H, 2 ꢁ NCH2CH2), 3.82 (s, 2H, ArCH2N),
6.62 (m, 2H, H-40 u. H-60), 7.20 (s, 1H, H-8), 7.47 (m, 1H, H-50),
8.20 (m, 1H, H-30), 9.13 (s, 1H, H-5); MS, m/z = 322 (M+); Anal.
(C18H22N6) C, H, N.
4.2.20. 7-Methyl-3-[(4-phenylpiperazin-1-yl)methyl]imidazo[1,2-c]
pyrimidine (30a)
This compound was obtained as an almost yellow powder in
a
yield of 0.14 g (35%). Mp 158–159 °C; IR 2939, 2828,
1630 cmꢀ1 1H NMR (CDCl3) d: 2.54 (s, 3H, Me-7), 2.62 (m, 4H,
;
2 ꢁ NCH2CH2), 3.17 (m, 4H, 2 ꢁ NCH2CH2), 3.90 (s, 2H, ArCH2N),
6.86 (m, 1H, H-40), 6.92 (m, 2H, H-20u. H-60), 7.25 (m, 2H, H-
30u. H-50), 7.30 (d, 1H, H-8, J = 1.4 Hz), 7.47 (d, 1H, H-2,
J = 1.4 Hz), 9.26 (s, 1H, H-5); MS, m/z = 307 (M+); Anal.
(C18H21N5) C, H, N.
4.2.14. 5,7-Dimethyl-3-[4-phenylpiperazin-1-ylmethyl]imidazo
[1,2-c]pyrimidine (29a)
This compound was obtained as a light ivory powder in a yield
of 0.19 g (46%). Mp 110–111 °C; IR 2954, 2925, 1631 cmꢀ1 1H
;
NMR (CDCl3) d: 2.47 (s, 3H, Me-7), 2.61 (m, 4H, 2 ꢁ NCH2CH2),
3.16 (m, 4H, 2 ꢁ NCH2CH2), 3.21 (s, 3H, Me-5), 3.82 (s, 2H, ArCH2N),
6.88 (m, 3H, H-20, H-40u. H-60), 7.16 (s, 1H, H-8), 7.25 (m, 2H, H-30 u.
H-50), 7.41 (s, 1H, H-2); MS, m/z = 321 (M+); Anal. (C19H23N5) C, H,
N.
4.2.21. 3-{[4-(4-Chlorophenyl)piperazin-1-yl]methyl}-7-
methylimidazo[1,2-c]pyrimidine (30b)
This compound, a light ivory powder, was gained in yields of
0.14 g (32%). Mp 128–129 °C; IR 2941, 2823, 1614, 1142 cmꢀ1
;
1H NMR (CDCl3) d: 2.62 (s, 3H, Me-7), 2.70 (m, 4H, 2 ꢁ NCH2CH2),
3.13 (m, 4H, 2 ꢁ NCH2CH2), 3.98 (s, 2H, ArCH2N), 6.81 (m, 2H, H-
20u. H-60), 7.18 (m, 2H, H-30u. H-50), 7.57 (d, 1H, H-8, J = 1.4 Hz),
7.63 (d, 1H, H-2, J = 1.4 Hz), 8.90 (s, 1H, H-5); MS, m/z = 343
(M+), 341 (M+); Anal. (C18H20ClN5) C, H, N.
4.2.15. 3-{[4-(4-Chlorophenyl)piperazin-1-yl]methyl}-5,7-
dimethylimidazo[1,2-c]pyrimidine (29b)
This compound, a pale powder, was obtained in yields of 0.17 g
(37%). Mp 172–173 °C; IR 2951, 2821, 1629, 1143 cmꢀ1 1H NMR
;
(CDCl3) d: 2.47 (s, 3H, Me-7), 2.60 (m, 4H, 2 ꢁ NCH2CH2), 3.12
(m, 4H, 2 ꢁ NCH2CH2), 3.19 (s, 3H, Me-5), 3.81 (s, 2H, ArCH2N),
7.15 (m, 2H, H-20u. H-60), 7.17 (s, 1H, H-8), 7.40 (m, 3H, H-2, H-
30u. H-50); MS, m/z = 357 (M+); 355 (M+); Anal. (C19H22ClN5) C, H,
N.
4.2.22. 3-{[4-(3,4-Dichlorophenyl)piperazin-1-yl]methyl}-7-
methylimidazo[1,2-c]pyrimidine (30c)
This derivative was made up as a pale powder in a yield of
0.17 g (42%). Mp 143–144 °C; IR 2943, 1614, 1140 cmꢀ1 1H NMR
;
(CDCl3) d: 2.62 (s, 3H, Me-7), 2.69 (m, 4H, 2 ꢁ NCH2CH2), 3.14
(m, 4H, 2 ꢁ NCH2CH2), 3.98 (s, 2H, ArCH2N), 6.70 (dd, 1H, H-60,
J1 = 3.0 Hz u. J2 = 8.9 Hz), 6.91 (d, 1H, H-20, J = 3.0 Hz), 7.24 (d, 1H,
H-50, J = 8.9 Hz), 7.58 (d, 1H, H-8, J = 1.5 Hz), 7.63 (d, 1H, H-2,
J = 1.5 Hz), 8.90 (s, 1H, H-5); MS, m/z = 315 (M+), 313 (M+), 311
(M+); Anal. (C18H19Cl2N5) C, H, N.
4.2.16. 3-{[4-(3,4-Dichlorophenyl)piperazin-1-yl]methyl}-5,7-
dimethylimidazo[1,2-c] pyrimidine (29c)
This compound, an ivory powder, was assembled in yields of
0.24 g (48%). Mp 192–193 °C; IR 2952, 2821, 1631, 1138 cmꢀ1
;
1H NMR (CDCl3) d: 2.47 (s, 3H, Me-7), 2.60 (m, 4H, 2 ꢁ NCH2CH2),