Month 2017
Functionalized Diphenyl-Imidazolo-Pyrimidines
J = 7.3 Hz, 2 H), 7.42 (t, J = 7.6 Hz, 2 H), 7.50 (t,
J = 7.3 Hz, 1 H), 7.78 (s, 1 H); C (100 MHz,
Ethyl 6-((2-bromo-4,5-diphenyl-1H-imidazol-1-yl)methyl)-4-
4-chlorophenyl)-1-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-
1
3
(
5
-carboxylate (17d).
DMSO-d ): δ = 164.8, 153.6, 145.7, 143.4, 138.1, 133.9,
6
1
1
1
31.4, 130.8, 129.8, 129.8, 129.3, 129.0, 128.7, 127.9,
27.2, 126.6, 126.3, 121.7, 107.7, 60.6, 52.1, 44.0, 31.1,
4.4. Anal. Calcd for C H BrN O : C, 63.05; H, 4.76;
3
0
27
4 3
N, 9.80. Found: C, 63.41; H, 4.42; N, 9.91.
Ethyl 6-((2-bromo-4,5-diphenyl-1H-imidazol-1-yl)methyl)-1-
methyl-2-oxo-4-(p-tolyl)-1,2,3,4-tetrahydropyrimidine-5-
carboxylate (17b).
1
White solid, yield 74%, mp 193–195°C; H NMR (400 MHz,
DMSO-d ): δ = 1.14 (t, J = 7.1 Hz, 3 H), 2.68 (s, 3 H), 3.96–
6
(
d, J = 4.4 Hz, 1 H), 5.18 (d, J = 17.1 Hz,
4
.03 (m, 2 H), 4.70
1
H), 6.44 (d, J = 17.1 Hz, 1 H), 7.12–7.14 (d, J = 8.0 Hz,
H), 7.16–7.21 (m, 3 H), 7.25 (d, J = 4.0 Hz, 2 H), 7.34–
.31 (m, 4 H), 7.41 (t, J = 7.6 Hz, 2 H), 7.49 (t, J = 7.3 Hz,
2
7
1
H), 7.87 (d, J = 3.9 Hz, 1 H); 13
C (100 MHz, DMSO-d6):
1
White solid, yield 81%, mp 220–223°C; H NMR
δ = 164.7, 153.4, 146.2, 142.3, 138.1, 133.8, 132.5, 131.2,
130.9, 129.8, 129.7, 129.3, 128.9, 128.7, 128.6, 127.2,
126.3, 121.7, 107.0, 60.7, 52.1, 44.0, 31.1, 14.4. Anal. Calcd
for C H BrClN O : C, 59.47; H, 4.33; N, 9.25. Found: C,
(
400 MHz, DMSO-d ): δ = 1.16 (t, J = 7.1 Hz, 3 H),
6
2
5
7
7
2
7
.23 (s, 3 H), 2.71 (s, 3 H), 4.01 (brs, 2 H), 4.72 (s, 1 H),
.13 (d, J = 12.0 Hz, 2 H), 6.40 (d, J = 12.0 Hz, 1 H),
.00 (d, J = 8.0 Hz, 2 H), 7.06 (d, J = 8.0 Hz, 2 H),
.14–7.21 (m, J = 6.8 Hz, 2 H), 7.26 (d, J = 4.0 Hz,
H), 7.33 (d, J = 4.0 Hz, 2 H), 7.42 (t, J = 5.4 Hz, 2 H),
30
26
4 3
59.85; H, 4.12; N, 9.47.
Ethyl 6-((2-bromo-4,5-diphenyl-1H-imidazol-1-yl)methyl)-4-
(4-bromophenyl)-1-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-
5-carboxylate (17e).
1
3
.49 (d, J = 6.3 Hz, 1 H), 7.69 (s, 1 H); C (100 MHz,
DMSO-d ): δ = 164.9, 153.6, 145.5, 140.4, 138.1, 137.1,
6
1
1
1
33.9, 131.4, 130.8, 129.8, 129.7, 129.5, 129.3, 128.7,
26.5, 126.3, 121.7, 107.8, 60.6, 52.3, 44.0, 31.1, 21.1,
4.4. Anal. Calcd for C H BrN O : C, 63.59; H, 4.99;
3
1
29
4 3
N, 9.57. Found: C, 63.24; H, 4.76; N, 9.32.
Ethyl 6-((2-bromo-4,5-diphenyl-1H-imidazol-1-yl)methyl)-4-
(
4-methoxyphenyl)-1-methyl-2-oxo-1,2,3,4-
tetrahydropyrimidine-5-carboxylate (17c).
1
White solid, yield 78%, mp 205–207°C; H NMR
(
400 MHz, DMSO-d ): δ = 1.15 (t, J = 7.1 Hz, 3 H),
6
2.69 (s, 3 H), 4.01 (q, J = 6.8 Hz, 2 H), 4.72 (brs, 1 H),
5.15 (d, J = 17.1 Hz, 1 H), 6.43 (d, J = 17.1 Hz, 1 H),
7.08 (d, J = 8.3 Hz, 2 H), 7.13–7.21 (m, 3 H), 7.25 (d,
J = 7.3 Hz, 2 H), 7.33 (d, J = 7.3 Hz, 2 H), 7.39–7.51
13
(
m, 5 H), 7.81 (s, 1 H); C (100 MHz, CDCl3):
δ = 164.6, 153.4, 146.2, 142.7, 138.1, 133.8, 131.8,
1
White solid, yield 77%, mp 223–224°C; H NMR
400 MHz, DMSO-d ): δ = 1.15 (t, J = 7.1 Hz, 3 H),
2
(
(
(
1
1
31.3, 130.9, 129.8, 129.7, 129.3, 128.9, 129.6, 127.2,
26.3, 121.2, 121.1, 107.0, 60.7, 52.1, 44.0, 31.1, 14.4.
(
6
.69 (s, 3 H), 3.69 (s, 3 H), 3.99 (m, 2 H), 4.67
Anal. Calcd for C H Br N O : C, 55.40; H, 4.03; N,
30
26
2 4 3
d, J = 3.4 Hz, 1 H), 5.15 (d, J = 17.1 Hz, 1 H), 6.43
d, J = 17.1 Hz, 1 H), 6.81 (d, J = 8.8 Hz, 2 H), 7.00
d, J = 8.8 Hz, 2 H), 7.12–7.18 (m, 3 H), 7.25 (d,
J = 7.3 Hz, 2 H), 7.33 (d, J = 4.0 Hz, 2 H), 7.41
t, J = 7.6 Hz, 2 H), 7.49 (t, J = 7.1 Hz, 1 H), 7.75
8
.61. Found: C, 55.12; H, 4.00; N, 8.72.
Ethyl 6-((2-bromo-4,5-diphenyl-1H-imidazol-1-yl)methyl)-1-
methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-
carboxylate (17f).
(
(
13
brs, 1 H); C (100 MHz, CDCl ): δ = 164.8, 159.0,
3
1
53.5, 145.3, 138.1, 135.5, 133.8, 131.4, 130.8, 129.8,
1
29.7, 129.3, 128.6, 127.8, 127.2, 126.2, 121.6,
114.2, 108.0, 60.5, 55.5, 52.1, 44.0, 31.0, 14.4. Anal.
Calcd for C H BrN O : C, 61.90; H, 4.86; N, 9.31.
31
29
4 4
Found: C, 61.74; H, 4.56; N, 9.48.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet