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HETEROCYCLES, Vol. 71, No. 2, 2007
5-Ethoxycarbonyl-6-methyl-4-(4-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-one (4c):18 1H NMR
(DMSO-d6, 300 MHz): δ 1.08 (t, 3H, J= 7.2 Hz), 2.27 (s, 3H), 3.98 (q, 2H, J= 7.2 Hz), 5.29 (d, 1H, J= 2.9
Hz), 7.51 (d, 2H, J= 8.5 Hz), 7.78 (s, 1H), 8.19 (d, 2H, J= 8.5 Hz), 9.29 (s, 1H).
5-Ethoxycarbonyl-6-methyl-4-(4-cyanophenyl)-3,4-dihydropyrimidin-2(1H)-one (4d): IR (KBr):
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3235, 3110, 2221, 1700, 1635 cm-1. H NMR (DMSO-d6, 300 MHz): δ 1.07 (t, 3H, J= 7.1 Hz), 2.25 (s,
3H), 3.97 (q, 2H, J= 7.1 Hz), 5.21 (s, 1H), 7.42 (d, 2H, J= 8.2 Hz), 7.80 (d, 2H, J= 8.2 Hz), 7.88 (s, 1H),
9.33 (s, 1H). 13C NMR (DMSO-d6, 75 MHz): δ 14.48, 18.29, 54.28, 59.79, 98.69, 110.55, 119.20, 127.81,
133.00, 149.77, 150.47, 152.28, 165.55.
5-Ethoxycarbonyl-6-methyl-4-(2-chlorophenyl)-3,4-dihydropyrimidin-2(1H)-one (4e): 1H NMR
(DMSO-d6, 300 MHz): δ 0.98 (t, 3H, J= 6.9 Hz), 2.29 (s, 3H), 3.88 (q, 2H, J= 6.8 Hz), 5.62 (s, 1H), 7.18-
7.34 (m, 3H), 7.40 (d, 1H, J= 7.3 Hz), 7.72 (s, 1H), 9.28 (s, 1H).
5-Ethoxycarbonyl-6-methyl-4-(3-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-one (4f): 1H NMR
(DMSO-d6, 400 MHz): δ 1.09 (t, 3H, J= 7.0 Hz), 2.26 (s, 3H), 3.99 (q, 2H, J= 7.0 Hz), 5.30 (d, 1H, J= 3.5
Hz), 7.64-7.69 (m, 2H), 7.91 (d, 1H), 8.08 (s, 1H), 8.13 (d, 1H, J= 7.8 Hz), 9.38 (s, 1H).
5-Ethoxycarbonyl-6-methyl-4-(4-methylphenyl)-3,4-dihydropyrimidin-2(1H)-one (4g): 1H NMR
(DMSO-d6, 400 MHz): δ 1.10 (t, 3H, J= 7.0 Hz), 2.25 (s, 3H), 3.97 (q, 2H, J= 7.0 Hz), 5.10 (d, 1H, J= 3.1
Hz), 7.10 (d, 4H, J= 3.2 Hz), 7.69 (s, 1H), 9.16 (s, 1H).
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5-Ethoxycarbonyl-6-methyl-4-(2-methoxyphenyl)-3,4-dihydropyrimidin-2(1H)-one (4h): H NMR
(DMSO-d6, 400 MHz): δ 1.02 (t, 3H, J= 7.0 Hz), 2.26 (s, 3H), 3.78 (s, 3H), 3.90 (q, 2H, J= 7.0 Hz), 5.48
(s, 1H), 6.80-7.05 (m, 3H), 7.22 (d, 1H, J= 7.8 Hz), 7.27 (s, 1H), 9.11 (s, 1H).
5-Ethoxycarbonyl-6-methyl-4-(4-methoxyphenyl)-3,4-dihydropyrimidin-2(1H)-one (4i):19 1H NMR
(DMSO-d6, 300 MHz): δ 1.16 (t, 3H, J= 7.2 Hz), 2.24(s, 3H), 3.76 (s, 3H), 3.98 (q, 2H, J= 7.2 Hz), 5.10
(d, 1H, J= 3.2 Hz), 6.79 (d, 2H, J= 8.7 Hz), 7.17 (d, 2H, J= 8.7 Hz), 7.25 (s, 1H), 8.94 (s, 1H).
5-Ethoxycarbonyl-6-methyl-4-(furyl)-3,4-dihydropyrimidin-2(1H)-one (4j):17 1H NMR (DMSO-d6,
300 MHz): δ 1.13 (t, 3H, J= 7.0 Hz), 2.22 (s, 3H), 4.02 (q, 2H, J= 6.9 Hz), 5.20 (d, 1H, J= 2.5 Hz), 6.09
(d, 1H, J= 2.3 Hz), 6.35 (s, 1H), 7.55 (s, 1H), 7.79 (s, 1H), 9.30 (s, 1H).
5-Ethoxycarbonyl-6-methyl-4-(thionyl)-3,4-dihydropyrimidin-2(1H)-one (4k):
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IR (KBr): 3228, 3116, 1700, 1640 cm-1. H NMR (DMSO-d6, 300 MHz): δ 1.15 (t, 3H, J= 7.0 Hz), 2.21
(s, 3H), 4.05 (q, 2H, J= 7.0 Hz), 5.40 (s, 1H), 6.88-6.93 (m, 2H), 7.34 (d, 1H, J= 4.5 Hz), 7.90 (s, 1H),
9.30 (s, 1H). 13C NMR (DMSO-d6, 75 MHz): δ 14.59, 18.12, 49.79, 59.84, 100.26, 123.98, 125.09,