1274
M. MIRZAI AND H. VALIZADEH
7
.14 (m, 1H, CH), 7.19 (d, 1H, J ¼ 6.23 Hz, CH), 7.29 (m, 1H, CH), 7.31 (br s, 1H,
6
1
3
NH), 9.09 (br s, 1H, NH). C NMR (DMSO-d ): d: 165.79, 156.54, 151.25, 150.13,
133.10, 128.11, 127.02, 119.32, 110.65, 97.10, 54.71, 49.13, 18.01, 17.04. Anal. calcd.
for C H N O (%): C, 55.08; H, 4.95; N, 13.76. Found: C, 56.08; H, 4.91; N, 13.50.
1
4
15
3
5
5
-Ethoxycarbonyl-(2-chlorophenyl)-6-methyl-3,4-dihydropyrimidine-
ꢁ
1
1
2
(1H)-one 4d. IR (KBr) tmax: 1650, 1711, 1719, 3118, 3243 cm
.
H NMR
(
DMSO-d ) d: 1.10 (t, 3H, J ¼ 7.12 Hz, CH ), 2.20 (s, 3H, CH ), 3.81 (q, 2H,
6
3
3
J ¼ 7.12 Hz, OCH ), 5.54 (d, 1H, J ¼ 2.89 Hz, CH), 6.99 (d, 1H, J ¼ 8.52 Hz, CH),
2
7
1
1
.13 (m, 1H, CH), 7.20 (d, 1H, J ¼ 6.19 Hz, CH), 7.26 (m, 1H, CH), 7.32 (br s,
1
3
H, NH), 8.89 (br s, 1H, NH). C NMR (DMSO-d ): d: 164.35, 155.69, 149.87,
6
48.32, 132.52, 127.96, 126.65, 117.78, 109.98, 100.21, 55.11, 48.64, 19.45, 16.53.
Anal. calcd. for C H ClN O (%): C, 57.05; H, 5.13; N, 9.50. Found: C, 58.01;
2
1
4
15
3
H, 5.12; N, 9.35.
5
-Ethoxycarbonyl-(2-methylphenyl)-6-methyl-3,4-dihydropyrimidine-2
ꢁ
1
1
(
1H)-one 4e. IR (KBr) tmax: 1661, 1702, 1713, 3122, 3245 cm
.
H NMR
(
DMSO-d ): d: 1.08 (t, 3H, J ¼ 7.15 Hz, CH ), 2.12 (s, 3H, CH ), 2.27 (s, 3H,
6
3
3
CH ), 3.81 (q, 2H, J ¼ 7.15 Hz, OCH ), 5.61 (d, 1H, J ¼ 2.78 Hz, CH), 6.98 (d,
3
2
1
1
1
5
6
H, J ¼ 8.43 Hz, CH), 7.05 (m, 1H, CH), 7.18 (d, 1H, J ¼ 6.23 Hz, CH), 7.25 (m,
1
3
H, CH), 7.33 (br s, 1H, NH), 9.01 (br s, 1H, NH). C NMR (DMSO-d): d:
59.02, 151.09, 148.37, 146.97, 130.02, 125.90, 122.15, 116.10, 108.90, 101.20,
8.01, 47.35, 45.04, 17.41, 14.03. Anal. calcd. for C H N O (%): C, 65.68; H,
1
5
18
2
3
.61; N, 10.21. Found: C, 66.02; H, 6.60; N, 10.18.
5
-Ethoxycarbonyl-(2-furyl)-6-methyl-3,4-dihydropyrimidine-2(1H)-one
ꢁ1 1
4
f. IR (KBr) tmax: 1664, 1701, 1715, 3120, 3241 cm . H NMR (DMSO-d ) d: 1.05
6
(
(
7
1
1
5
t, 3H, J ¼ 7.46 Hz, CH ). 2.19 (s, 3H, CH ), 3.78 (q, 2H, J ¼ 7.46 Hz, OCH ), 5.64
3
3
2
d, 1H, J ¼ 2.35 Hz, CH), 6.78 (dd,1H, J ¼ 7.23, 2.38 Hz, CH), 7.03 (dd, 1H, J ¼ 7.23,
.36 Hz, CH), 7.18 (dd, 1H, J ¼ 2.38, 7.36 Hz, CH), 7.36 (br s, 1H, NH), 9.77 (br s,
1
3
H, NH), C NMR (DMSO-d ): d: 161.02, 154.21, 133.23, 131.23, 127.11, 124.17,
6
04.19, 102.96, 98.35, 59.65, 42.04, 14.03. Anal. calcd. for C H N O (%): C,
7.59; H, 5.64; N, 11.19. Found: C, 58.12; H, 5.65; N, 11.13.
1
2
14
2
4
5
-Ethoxycarbonyl-4-phenyl-6-methyl-3,4-dihydropyrimidine-2(1H)-thione
ꢁ
1
1
4
g. IR (KBr) tmax: 1645, 1678, 1702, 3110, 3248 cm
.
H NMR (DMSO-d6,
4
00 MHz) d: 1.12 (t, 3H, J ¼ 7.11 Hz,), 2.27 (s, 3H), 3.99 (q, 2H, J ¼ 7.11 Hz), 5.21
(
d, 1H, J ¼ 3.24 Hz), 7.24–7.35 (m, 5H, ArH), 7.77 (s, 1H, NH), 8.87 (s, 1H, NH).
1
3
C NMR (DMSO-d , 150 MHz) d: 158.25, 145.56, 139.11, 138.25, 125.56, 124.98,
6
1
6
22.85, 100.54, 61.75, 53.43, 20.12, 14.52. Anal. calcd. for C H N O S (%): C,
0.85; H, 5.84; N, 1014. Found: C, 60.89; H, 5.85; N, 10.11.
1
4
16
2
2
5
-Ethoxycarbonyl-(4-methoxyphenyl)-6-methyl-3,4-dihydropyrimidine-2
ꢁ
1
1
(
1H)-thione 4h. IR (KBr) tmax: 1646, 1702, 1720, 3121, 3241 cm . H NMR
(
DMSO-d , 400 MHz) d: 1.18 (t, 3H, J ¼ 7.13 Hz), 2.26 (s, 3H, Me), 3.85 (s, 3H,
6
OMe), 3.98 (q, 2H, J ¼ 7.13 Hz), 5.15 (d, 1H, J ¼ 3.51 Hz), 7.11–7.20 (m, 4H,
1
3
ArH), 7.69 (s, 1H, NH), 8.98 (s, 1H, NH). C NMR (DMSO-d , 150 MHz) d:
6
1
63.21, 155.42, 151.12, 142.52, 127.89, 113.63, 107.45, 101.52, 60.78, 59.11, 57.75,