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I. Selin Zorkun et al. / Bioorg. Med. Chem. 14 (2006) 8582–8589
8587
1H, H-4), 7.20–7.60 (m, 4H, C6H4), 9.75 (s, 1H, N3H),
10.45 (s, 1H, N1H); IR (KBr): 3168, 2976, 1684, 1588,
1462, 1435, 1342, 1274, 1196, 1108, 764 cmÀ1; MS
(70 eV, EI): m/z (%): 358 (M+2, 55.29), 356 (M+,
55.29), 341, 325, 295, 275, 213, 199 (MÀAr, 100), 167.
4.1.15. 6-Ethyl-4-(3-nitrophenyl)-5-(methoxycarbonyl)-
3,4-dihydropyrimidin-2(1H)-thione (12). Mp 201–
203 ꢁC; 1H NMR: d = 1.10 (t, 3H, CH3), 2.40–2.95
(m, 2H, CH2), 3.55 (s, 3H, OCH3), 5.35 (d, 1H, H-
4), 7.70–8.10 (m, 4H, C6H4), 9.80 (s, 1H, N3H),
10.50 (s, 1H, N1H); IR (KBr): 3317, 3215, 2925,
1660, 1579, 1529, 1461, 1439, 1348, 1283, 1188,
1126, 758, 741, 693 cmÀ1; MS (70 eV, EI): m/z (%):
321 (M+, 74.52), 304, 288, 274, 262, 216, 199 (MÀAr,
100), 183, 167; Anal. Calcd for C14H15N3O4S: C,
52.33; H, 4.71; N, 13.08. Found: C, 53.40; H, 5.16;
N, 12.47.
4.1.10. 6-Ethyl-4-(2-methylphenyl)-5-(methoxycarbonyl)-
3,4- dihydropyrimidin-2(1H)-thione (7). Mp 181–183 ꢁC,
lit.32 192–193 ꢁC; 1H NMR: d = 1.13 (t, 3H, CH3),
2.48 (s, 3H, Ar-CH3), 2.48 (m, 2H, CH2), 3.46 (s, 3H,
OCH3), 5.39 (d, 1H, H-4), 7.12-7.17 (m, 4H, C6H4),
9.52 (s, 1H, N3H), 10.29 (s, 1H, N1H); IR (KBr):
3270, 3169, 3009, 2972, 1690, 1631, 1580, 1461, 1434,
1311, 1187, 1136, 1101, 755 cmÀ1; MS (70 eV, EI): m/z
(%): 290 (M+, 59.13), 275, 259, 231 (MÀCOOCH3,
100), 213, 199, 185, 167.
4.1.16. 6-Ethyl-4-(2-fluorophenyl)-5-(methoxycarbonyl)-
3,4-dihydropyrimidin-2(1H)-thione (13). Mp 183–
1
185 ꢁC; H NMR: d = 1.10 (t, 3H, CH3), 2.67–2.73 (m,
2H, CH2), 3.49 (s, 3H, OCH3), 5.43 (d, 1H, H-4),
7.14–7.22 (m, 4H, C6H4), 9.56 (s, 1H, N3H), 10.39 (s,
1H, N1H); IR (KBr): 3265, 3179, 2934, 1699, 1642,
1576, 1485, 1462, 1436, 1313, 1273, 1225, 1189, 1149,
1132, 1105, 759 cmÀ1; MS (70 eV, EI): m/z (%): 294
(M+, 51.44), 279, 265, 235, 216, 199 (MÀAr, 100), 167;
Anal. Calcd for C14H15N2O2SF: C, 57.13; H, 5.14; N,
9.52. Found: C, 56.59; H, 4.47; N, 9.47.
4.1.11. 6-Ethyl-4-(3-methylphenyl)-5-(methoxycarbonyl)-
3,4-dihydropyrimidin-2(1H)-thione (8). Mp 170–171 ꢁC,
lit.32 178–179 ꢁC; 1H NMR: d = 1.08 (t, 3H, CH3),
2.25 (s, 3H, Ar-CH3), 2.63–2.75 (m, 2H, CH2), 3.53 (s,
3H, OCH3), 5.09 (d, 1H, H-4), 6.96–7.22 (m, 4H,
C6H5), 9.61 (s, 1H, N3H), 10.32 (s, 1H, N1H); IR
(KBr): 3333, 3180, 3112, 2980, 1664, 1578, 1460, 1437,
1348, 1283, 1187, 1116, 757, 704 cmÀ1; MS (70 eV,
EI): m/z (%): 290 (M+, 91.35), 275, 259, 231, 213, 199
(MÀAr, 100), 185, 167.
4.1.17. 6-Ethyl-4-(3-fluorophenyl)-5-(methoxycarbonyl)-
3,4-dihydropyrimidin-2(1H)-thione (14). Mp 150–
152 ꢁC; 1H NMR: d = 1.09 (t, 3H, CH3), 2.62–2.78
(m, 2H, CH2), 3.56 (s, 3H, OCH3), 5.17 (d, 1H,
H-4), 7.38–7.43 (m, 4H, C6H4), 9.71 (d, 1H, N3H),
10.45 (s, 1H, N1H); IR (KBr): 3321, 2925, 1663,
1572, 1461, 1350, 1280, 1189, 1117, 786 cmÀ1; MS
(70 eV, EI): m/z (%): 294 (M+, 82.21), 279, 263, 235,
213, 199 (MÀAr, 100), 167; Anal. Calcd for
C14H15N2O2SF: C, 57.13; H, 5.14; N, 9.52. Found:
C, 57.38; H, 5.60; N, 9.43.
4.1.12. 6-Ethyl-4-(4-methylphenyl)-5-(methoxycarbonyl)-
3,4- dihydropyrimidin-2(1H)-thione (9). Mp 176–178 ꢁC;
1H NMR: d = 1.08 (t, 3H, CH3), 2.25 (s, 3H, Ar-CH3),
2.62–2.75 (m, 2H, CH2), 3.53 (s, 3H, OCH3), 5.10 (d,
1H, H-4), 7.06–7.14 (m, 4H, C6H4), 9.61 (s, 1H, N3H),
10.33 (s, 1H, N1H); IR (KBr): 3168, 2978, 1688, 1647,
1590, 1511, 1462, 1343, 1275, 1196, 1111, 769 cmÀ1
;
MS (70 eV, EI): m/z (%): 290 (M+, 88.03), 275, 261,
231, 213, 199 (MÀAr, 100), 167. Anal. Calcd for
C15H18N2O2S: C, 62.04; H, 6.24; N, 9.64. Found: C,
62.31; H, 6.19; N, 9.47.
4.1.18. 6-Ethyl-4-(2-ethoxyphenyl)-5-(methoxycarbonyl)-
3,4-dihydropyrimidin-2(1H)-thione (15). Mp 204–206 ꢁC;
1H NMR: d = 1.09 (t, 3H, CH3), 1.37 (t, 3H, Ar-CH3),
2.63–2.68 (m, 2H, CH2), 3.33 (s, 3H, OCH3), 3.96–4.04
(m, 2H, Ar-OCH2), 5.41 (d, 1H, H-4), 6.82–7.23 (m,
4H, C6H4), 9.12 (s, 1H, N3H), 10.22 (s, 1H, N1H); IR
(KBr): 3309, 3177, 3105, 2975, 2932, 1711, 1650, 1579,
1484, 1433, 1338, 1299, 1258, 1233, 1181, 1131, 1101,
1034, 758 cmÀ1; MS (70 eV, EI): m/z (%): 320 (M+,
100), 305, 291, 275, 261, 242, 231, 216, 199, 185, 167;
Anal. Calcd for C16H20N2O3S: C, 59.98; H, 6.29; N,
8.74. Found: C, 59.32; H, 6.81; N, 8.64.
4.1.13. 6-Ethyl-4-(2-methoxyphenyl)-5-(methoxycarbon-
yl)-3,4-dihydropyrimidin-2(1H)-thione (10). Mp 231 ꢁC,
lit.32 235–236 ꢁC; 1H NMR: d = 1.10 (t, 3H, CH3),
2.40–3.00 (m, 2H, CH2), 3.50 (s, 3H, Ar-OCH3), 3.75
(s, 3H, OCH3), 5.50 (d, 1H, H-4), 6.60–7.50 (m, 4H,
C6H4), 9.25 (s, 1H, N3H), 10.25 (s, 1H, N1H); IR
(KBr): 3194, 2972, 2931, 1713, 1661, 1571, 1487, 1470,
1428, 1277, 1245, 1177, 1132, 1102, 758 cmÀ1; MS
(70 eV, EI): m/z (%): 306 (M+, 100), 291, 273, 247,
231, 216, 199, 167.
4.1.19.
6-Ethyl-4-(5-bromo-2-hydroxyphenyl)-5-(meth-
(16).
4.1.14. 6-Ethyl-4-(2-nitrophenyl)-5-(methoxycarbonyl)-
3,4-dihydropyrimidin-2(1H)-thione (11). Mp 159–
161 ꢁC; H NMR: d = 1.18 (t, 3H, CH3), 2.75–2.77 (m,
oxycarbonyl)-3,4-dihydropyrimidin-2(1H)-thione
Mp 209–211 ꢁC; 1H NMR: d = 1.00 (t, 3H, CH3),
1.95–2.40 (m, 2H, CH2), 3.35 (s, 3H, OCH3), 3.75 (s,
H, OH), 4.70 (s, 1H, H-4), 6.90–7.40 (m, 3H, C6H3),
9.05 (s, 1H, N3H), 10.02 (s, 1H, N1H); IR (KBr):
3309, 3177, 3105, 2975, 2932, 1711, 1650, 1579, 1484,
1433, 1338, 1299, 1258, 1233, 1181, 1131, 1101, 1034,
758 cmÀ1; MS (70 eV, EI): m/z (%): 374 (M+2,
85.17), 372 (M+, 85.17), 355, 339, 311, 295, 280, 199
(MÀAr, 100), 167; Anal. Calcd for C14H16N2O3SBr:
C, 45.17; H, 4.33; N, 7.52. Found: C, 45.59; H, 4.46;
N, 7.59.
1
2H, CH2), 3.39 (s, 3H, OCH3), 5.56 (d, 1H, H-4),
7.46–7.55 (m, 4H, C6H4), 9.68 (s, 1H, N3H), 10.52 (s,
1H, N1H); IR (KBr): 3275, 3173, 2974, 2949, 1718,
1654, 1558, 1523, 1470, 1438, 1351, 1309, 1270, 1200,
1180, 1127, 1101, 750 cmÀ1; MS (70 eV, EI): m/z (%):
321 (M+, 9.62), 303, 273, 244, 228, 216 (MÀOCH3,
–C2H5, –NO2, 100), 199, 128; Anal. Calcd for
C14H15N3O4S: C, 52.33; H, 4.71; N, 13.07. Found: C,
52.87; H, 4.74; N, 12.99.