Molecules 2007, 12
1346
1
4.28, 18.78, 44.47, 55.23, 60.15, 101.60, 112.05, 125.65, 134.25, 141.16, 153.46, 159.02, 165.24; IR
–
1
(
ν
max.; KBr, cm ): 3242, 1721, 1637; ESI-MS 304 (M+H); HRMS calcd. for C16
H
21
N
3
O
3
303.1583
found 303.1585.
5
2
=
–(Ethoxycarbonyl)–4–(4-nitrophenyl)–6–methyl–3,4–dihydropyrimidin–2(1H)–one (4d): Mp 211–
1
13 °C; H-NMR (DMSO-d ) δ: 1.11 (t, 3H, J = 7.04 Hz, OCH CH ), 2.32 (s, 3H, CH ), 4.03 (q, 2H, J
6
2
3
3
7.12 Hz, OCH CH ), 5.78 (d, 1H, J = 2.28, -CH), 7.51 (d, 2H, J = 9.18, Ar-H), 7.69 (s, 1H, NH),
2
3
1
3
8
1
1
6
.16 (d, 2H, J = 9.16, Ar-H), 9.05 (s, 1H, NH); C-NMR (DMSO-d ) δ: 14.22, 18.71, 55.81, 60.15,
–
1
01.60, 118.15, 130.37, 138.34, 152.26, 153.41, 159.15, 165.85; IR (νmax.; KBr, cm ): 3235, 1740,
631; ESI-MS 306 (M+H); HRMS calcd. for C H N O 305.1012 found 305.1010.
1
4
15
3
5
5
2
=
–(Ethoxycarbonyl)–4–(4-chlorophenyl)–6–methyl–3,4–dihydropyrimidin–2(1H)–one (4e): Mp 215–
1
16 °C; H-NMR (DMSO-d ) δ: 1.12 (t, 3H, J = 7.14 Hz, OCH CH ), 2.30 (s, 3H, CH ), 3.91 (q, 2H, J
6
2
3
3
7.16 Hz, OCH
2 3
CH ), 5.70 (d, 1H, J = 2.28, -CH), 7.21 (d, 2H, J = 9.18, Ar-H), 7.69 (s, 1H, NH),
1
3
7
1
1
.94 (d, 2H, J = 9.18, Ar-H), 9.16 (s, 1H, NH); C-NMR (DMSO-d ) δ: 14.18, 18.62, 55.72, 60.21,
6
–
1
01.55, 118.17, 130.32, 142.29, 152.31, 153.39, 159.17, 165.83; IR (νmax.; KBr, cm ): 3225, 1720,
615; ESI-MS 295 (M+H); HRMS calcd. for C14 294.0771 found 294.0773.
2 3
H15ClN O
5
–(Ethoxycarbonyl)–4–(3-chlorophenyl)–6–methyl–3,4–dihydropyrimidin–2(1H)–one (4f): Mp 192–
1
1
93 °C; H-NMR (DMSO-d
6
) δ: 1.10 (t, 3H, J = 7.14 Hz, OCH
), 5.65 (d, 1H, J = 2.28, -CH), 7.25-7.41 (m, 4H, Ar-H), 7.61 (s, 1H, NH), 9.11
s, 1H, NH); C-NMR (DMSO-d ) δ: 14.17, 18.60, 55.70, 60.20, 101.52, 126.312, 127.92, 128.42,
30.29, 135.51, 142.21, 153.23, 159.32, 165.75; IR (νmax.; KBr, cm ): 3234, 1724, 1631; ESI-MS 295
M+H); HRMS calcd. for C14 294.0771 found 294.0772.
2 3 3
CH ), 2.28 (s, 3H, CH ), 3.88 (q, 2H, J
=
2 3
7.16 Hz, OCH CH
1
3
(
6
–
1
1
(
2 3
H15ClN O
5
–(Ethoxycarbonyl)–4–(3-bromophenyl)–6–methyl–3,4–dihydropyrimidin–2(1H)–one (4g): Mp 185–
1
1
86 °C; H-NMR (DMSO-d
6
) δ: 1.02 (t, 3H, J = 7.05 Hz, OCH
2
CH
3
), 2.30 (s, 3H, CH
3
), 3.75 (q, 2H, J
=
7.05 Hz, OCH CH ), 5.41 (d, 1H, J = 2.25, -CH), 7.05-7.34 (m, 4H, Ar-H), 7.51 (s, 1H, NH), 9.05 (s,
2 3
1
3
1
1
H, NH); C-NMR (DMSO-d
6
) δ: 14.16, 18.59, 55.74, 60.18, 101.57, 126.35, 127.82, 128.48, 130.32,
–
1
35.59, 143.94, 153.21, 159.30, 165.74; IR (νmax.; KBr, cm ): 3212, 1731, 1620; ESI-MS 339 (M+H);
HRMS calcd. for C H BrN O 338.0266 found 338.0268.
1
4
15
2
3
5
2
2
9
1
–(Ethoxycarbonyl)–4–(2,4-dichlorophenyl)–6–methyl–3,4–dihydropyrimidin–2(1H)–one (4h): Mp
1
49–250 °C; HNMR (DMSO-d
6
) δ: 1.18 (t, 3H, J = 7.23 Hz, OCH
), 5.92 (d, 1H, J = 2.30, -CH), 7.21-7.51 (m, 3H, Ar-H), 7.69 (s, 1H, NH),
.16 (s, 1H, NH); C-NMR (DMSO-d ) δ: 14.20, 18.60, 55.75, 60.24, 101.56, 127.82, 128.91, 129.52,
31.29, 142.52, 143.25, 153.23, 159.32, 165.75; IR (νmax.; KBr, cm ): 3255, 1731, 1651; ESI-MS 329
328.0381 found 328.0379.
2 3 3
CH ), 2.64 (s, 3H, CH ), 4.07 (q,
2 3
H, J = 7.24 Hz, OCH CH
1
3
6
–
1
(
M+H); HRMS calcd. for C14
H14Cl
N
2 2
O
3
5
–(Methoxycarbonyl)–4–(4-chlorophenyl)–6–methyl–3,4–dihydropyrimidin–2(1H)–one (4i): Mp 204–
1
2
05 °C; H-NMR (DMSO-d
6
) δ: 2.30 (s, 3H, CH
3
), 3.92 (s, 3H, COOCH
3
), 5.44 (d, 1H, J = 2.15, -
CH), 7.14 (d, 2H, J = 9.05, Ar-H), 7.51 (s, 1H, NH), 7.87 (d, 2H, J = 9.06, Ar-H), 9.02 (s, 1H, NH);