Shi et al.
FULL PAPER
δ: 3.14 (s, 6H, 2×CH3), 3.22 (s, 6H, 2×CH3), 6.81 (d,
J=8.8 Hz, 2H, ArH), 8.23 (s, 1H, CH=), 8.43 (d, J=
8.8 Hz, 2H, ArH); IR (KBr) ν: 1713, 1659, 1608, 1572,
1535, 1468, 1442, 1411, 1362, 1234, 1193, 1160, 998,
C14H15N3O3: C 61.53, H 5.53, N 15.38; found C 61.74,
H 5.40, N 15.57.
1-Methyl-5-(4-methoxybenzylidene)pyrimidine-2,-
4,6(1H,3H,5H)-trione (5h) m.p. 242—244 ℃; 1H
NMR (DMSO-d6, 400 MHz) δ: 3.15 (s) and 3.18 (s) (3H,
CH3), 3.88 (s, 3H, CH3O), 7.06—7.08 (m, 2H, ArH),
8.27 (s) and 8.30 (s) (1H, CH=), 8.34—8.39 (m, 2H,
ArH), 11.41 (s) and 11.52 (s) (1H, NH); IR (KBr) ν:
3230, 1723, 1693, 1604, 1571, 1550, 1388, 1348, 1188,
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971, 940, 786, 752 cm .
1,3-Dimethyl-5-(4-methyoxybenzylidene)pyrimi-
dine-2,4,6(1H,3H,5H)-trione (5b) m.p. 149—151 ℃
(Lit.20 152 ℃); 1H NMR (DMSO-d6, 400 MHz) δ: 3.21
(s, 3H, CH3), 3.23 (s, 3H, CH3), 3.87 (s, 3H, CH3O),
7.08 (d, J=9.2 Hz, 2H, ArH), 8.32 (s, 1H, CH=), 8.34
(d, J=9.2 Hz, 2H, ArH); IR (KBr) ν: 1717, 1664, 1603,
1569, 1463, 1433, 1406, 1382, 1229, 1185, 850, 817,
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1
1147, 983, 842, 756 cm . Anal. calcd for C13H12N2O4:
C 60.00, H 4.65, N 10.76; found C 60.21, H 4.53, N
10.89.
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790, 752 cm .
1-Methyl-5-(3,4-methylenedioxybenzylidene)pyri-
midine-2,4,6(1H,3H,5H)-trione (5i) m.p. 287—289
℃; 1H NMR (DMSO-d6, 400 MHz) δ: 3.15 (s) and 3.17
(s) (3H, CH3), 6.19 (s, 2H, OCH2O), 7.09 (d, J=8.4 Hz,
1H, ArH), 7.75 (s, 1H, ArH), 8.18—8.26 (m, 2H and
CH=), 11.44 (s) and 11.54 (s) (1H, NH); IR (KBr) ν:
3225, 1731, 1641, 1548, 1503, 1359, 1260, 1029, 978,
1,3-Dimethyl-5-(3,4-methylenedioxybenzylidene)-
pyrimidine-2,4,6(1H,3H,5H)-trione (5c) m.p. 202—
204 ℃; 1H NMR (DMSO-d6, 400 MHz) δ: 3.22 (s, 3H,
CH3), 3.24 (s, 3H, CH3), 6.19 (s, 2H, OCH2O), 7.09 (d,
J=8.4 Hz, 1H, ArH), 7.74 (dd, J=1.6, 8.4 Hz, 1H,
ArH), 8.17 (d, J=1.6 Hz, 1H, ArH), 8.29 (s, 1H, CH=);
IR (KBr) ν: 1728, 1657, 1596, 1553, 1363, 1344, 1148,
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1
908, 783, 752 cm . Anal. calcd for C13H10N2O5: C
56.94, H 3.68, N 10.22; found C 56.81, H 3.53, N 10.41.
1-Methyl-5-(4-hydroxybenzylidene)pyrimidine-2,
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887, 814, 787, 752 cm . Anal. calcd for C14H12N2O5: C
58.33, H 4.20, N 9.72; found C 58.59, H 4.02, N 9.85.
1,3-Dimethyl-5-(4-hydroxybenzylidene)pyrimi-
dine-2,4,6(1H,3H,5H)-trione (5d) m.p. 293—295 ℃
(Lit.21 297—299 ℃); 1H NMR (DMSO-d6, 400 MHz) δ:
3.21 (s, 3H, CH3), 3.23 (s, 3H, CH3), 6.89 (d, J=8.4 Hz,
2H, ArH), 8.29 (d, J=8.4 Hz, 2H, ArH), 8.33 (s, 1H,
CH=), 10.84 (s, 1H, OH); IR (KBr) ν: 3200, 1705,
1667, 1639, 1602, 1470, 1420, 1397, 1385, 1298, 1252,
1
4,6(1H,3H,5H)-trione (5j) m.p.>300 ℃; H NMR
(DMSO-d6, 400 MHz) δ: 3.16 (s) and 3.17 (s) (3H,
CH3), 6.89 (d, J=7.6 Hz, 2H, ArH), 8.23 (s) and 8.26 (s)
(1H, CH=), 8.31—8.35 (m, 2H, ArH), 10.84 (s, 1H,
OH), 11.36 (s) and 11.47 (s) (1H, NH); IR (KBr) ν:
3228, 1716, 1690, 1649, 1609, 1537, 1389, 1217, 1176,
985, 956, 844, 790, 756 cm - 1. Anal. calcd for
C12H10N2O4: C 58.54, H 4.09, N 11.38; found C 58.78,
H 3.86, N 11.51.
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1235, 885, 827, 789, 753 cm .
1,3-Dimethyl-5-(3,4-dimethylbenzylidene)pyri-
midine-2,4,6(1H,3H,5H)-trione (5e) m.p. 210—212
℃; 1H NMR (DMSO-d6, 400 MHz) δ: 2.28 (s, 3H, CH3),
2.32 (s, 3H, CH3), 3.21 (s, 3H, CH3), 3.24 (s, 3H, CH3),
7.28 (d, J=8.0 Hz, 1H, ArH), 7.94 (s, 1H, ArH), 7.97 (d,
J=8.0 Hz, 1H, ArH), 8.31 (s, 1H, CH=); IR (KBr) ν:
1722, 1665, 1574, 1555, 1506, 1448, 1420, 1361, 1241,
1-Methyl-5-(3,4-dimethoxybenzylidene)pyrimi-
dine-2,4,6(1H,3H,5H)-trione (5k) m.p. 265—267 ℃;
1H NMR (DMSO-d6, 400 MHz) δ: 3.16 (s) and 3.17 (s)
(3H, CH3), 3.81—3.88 (m, 6H, 2×CH3O), 7.11 (d, J=
8.8 Hz, 2H, ArH), 7.87—7.94 (m, 1H, CH = ),
8.26—8.41 (m, 2H, ArH), 11.41 (s) and 11.51 (s) (1H,
NH); IR (KBr) ν: 3210, 1732, 1687, 1658, 1549, 1509,
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1224, 1178, 987, 965, 917, 845, 792, 752, 723 cm .
Anal. calcd for C15H16N2O3: C 66.16, H 5.92, N 10.29;
found C 66.04, H 6.08, N 10.51.
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1357, 1289, 1014, 930, 892, 801, 751 cm . Anal. calcd
for C14H14N2O5: C 57.93, H 4.86, N 9.65; found C 58.04,
H 4.79, N 9.83.
1,3-Dimethyl-5-(3,4-dimethoxybenzylidene)pyri-
midine-2,4,6(1H,3H,5H)-trione (5f) m.p. 226—228
℃; 1H NMR (DMSO-d6, 400 MHz) δ: 3.23 (s, 3H, CH3),
3.25 (s, 3H, CH3), 3.83 (s, 3H, CH3O), 3.90 (s, 3H,
CH3O), 7.13 (d, J=8.4 Hz, 1H, ArH), 7.92 (d, J=8.4
Hz, 1H, ArH), 8.29 (s, 1H, ArH), 8.34 (s, 1H, CH=);
IR (KBr) ν: 1720, 1657, 1598, 1556, 1360, 1334, 1170,
1033, 922, 804, 771, 753 cm - 1. Anal. calcd for
C15H16N2O5: C 59.21, H 5.30, N 9.21; found C 59.36, H
5.12, N 9.09.
5,5'-(3,4-Dichlorophenylmethylene)bis(6-amino-1,
3-dimethylpyrimidine-2,4(1H,3H)-dione) (6a) m.p.
1
>300 ℃; H NMR (DMSO-d6, 400 MHz) δ: 3.06 (s,
6H, 2×CH3), 3.24 (s, 6H, 2×CH3), 5.57 (s, 1H, CH),
7.10 (d, J=9.2 Hz, 1H, ArH), 7.31—7.44 (m, 5H, ArH
+2×NH2), 7.89 (s, 1H, ArH); IR (KBr) ν: 3389, 3139,
1693, 1661, 1610, 1499, 1381, 1251, 1029, 881, 822,
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788, 755 cm . Anal. calcd for C19H20Cl2N6O4: C 48.83,
H 4.31, N 17.98; found C 49.05, H 4.14, N 18.18.
5,5'-(2,4-Dichlorophenylmethylene)bis(6-amino-1,
3-dimethylpyrimidine-2,4(1H,3H)-dione) (6b) m.p.
1-Methyl-5-(4-(dimethylamino)benzylidene)pyri-
midine-2,4,6(1H,3H,5H)-trione (5g) m.p. 268—270
1
1
℃; H NMR (DMSO-d6, 400 MHz) δ: 3.12 (s, 6H, 2×
>300 ℃; H NMR (DMSO-d6, 400 MHz) δ: 3.02 (s,
CH3), 3.17 (s, 3H, CH3), 6.82 (d, J=8.8 Hz, 2H, ArH),
8.21 (s, 1H, CH=), 8.43 (d, J=8.8 Hz, 2H, ArH),
11.17 (s) and 11.27 (s) (1H, NH); IR (KBr) ν: 3225,
1713, 1659, 1608, 1572, 1468, 1442, 1362, 1318, 1160,
998, 940, 830, 786, 752 cm - 1. Anal. calcd for
6H, 2×CH3), 3.21 (s, 6H, 2×CH3), 5.52 (s, 1H, CH),
7.15 (d, J=9.2 Hz, 1H, ArH), 7.28—7.40 (m, 5H, ArH
+2×NH2), 7.85 (s, 1H, ArH); IR (KBr) ν: 3379, 3130,
1695, 1661, 1605, 1496, 1380, 1193, 1029, 881, 788,
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755, 717 cm . Anal. calcd for C19H20Cl2N6O4: C 48.83,
794
© 2010 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2010, 28, 791— 796