KARIMIAN ET AL.
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1,650.20, 1,465.75. H NMR (400 MHz, CDCl3, ppm) δ:
8.82 (s, 1H, NH), 7.30–7.22 (m, 5H, ArH), 6.21 (s, 1H,
NH), 5.50 (d, J = 2.4 Hz, 1H, CH), 4.11 (q, J = 8.2 Hz,
2H, OCH2), 2.36 (s, 3H, CH3), 1.15 (t, J = 7.2 Hz, 3H,
CH3). 13C NMR (100 MHz, CDCl3, ppm) δ: 168.0, 153.62,
145.48, 143.85, 128.70, 127.93, 126.61, 101.30, 60.01,
55.90, 18.61, 16.15; MS (EI): m/z (%) 260. Anal. Calcd for
C14H16N2O3: C, 64.60; H, 6.20; N, 10.76; found: C,
64.63; H, 6.20; N, 10.79%.
J = 8.4 Hz, 4H, ArH), 5.10 (d, J = 3.0 Hz, 1H, CH), 3.99
(q, J = 7.1 Hz, 2H, OCH2), 3.69 (s, 3H, OCH3), 2.25 (s,
3H, CH3), 1.11 (t, J = 7.1 Hz, 3H, CH3). 13C NMR
(100 MHz, DMSO-d6, ppm) δ: 165.84, 158.97, 152.61,
147.45, 137.52, 127.65, 114.17, 100.02, 59.64, 55.53, 53.78,
19.22, 15.04. MS (EI): m/z (%) 290. Anal. Calcd for
C15H18N2O4: C, 62.06; H, 6.25; N, 9.65; found: C,
62.07; H, 6.25; N, 9.68%.
3.19 | Ethyl 6-methyl-2-oxo-4-(thiophen-
2-yl)-1,2,3,4-tetrahydropyrimidine-
5-carboxylate (6e)
3.16 | Ethyl 4-(4-chlorophenyl)-6-methyl-
2-oxo-1,2,3,4-tetrahydropyrimidine-
5-carboxylate (6b)
White Solid; mp 210–212ꢀC (Lit. 210ꢀC[47]). FT-IR (KBr,
disk) ν: 3,335, 3,233, 3,120, 2,975, 1,700, 1,651, 1,460, 1,220,
White solid; mp 208–209ꢀC (Lit. 207–209ꢀC[27]). (KBr,
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disk) ν: 3,330, 3,318, 1,745, 1,715, 1,455, 1,220, 850. H
1,095, 750 cm−1. H NMR (400 MHz, DMSO-d6, ppm) δ:
NMR (400 MHz, DMSO-d6, ppm) δ: 9.70 (s, 1H, NH),
8.55 (s, 1H, NH), 7.20–7.37 (m, 4H, CH), 5.12 (s, 1H, CH),
3.93–3.95 (m, 2H, CH), 2.20 (s, 3H, CH), 1.08 (t, 3H, CH,
J = 7.4 Hz). 13C NMR (100 MHz, DMSO-d6, ppm) δ:
161.9, 155.0, 132.3, 130.9, 128.5, 128.4, 126.6, 124.3, 124.1,
120.5, 54.2, 49.0, 19.18, 17.0. MS (EI): m/z (%) 294. Anal.
Calcd for C14H15ClN2O3: C, 57.05; H, 5.13; N, 9.50;
found: C, 57.05; H, 5.11; N, 9.48%.
9.28 (s, 1H, NH). 7.92 (s, 1H, NH), 7.35 (s, 1H), 6.88–6.90
(m, 2H), 5.41 (s, 1H), 4.00–4.05 (m, 2H), 2.23 (s, 3H, CH3),
1.11 (t, J = 7.2 Hz, 3H, CH3). MS (EI): m/z (%) 266. Anal.
Calcd for C12H14N2O3S2: C, 54.12; H, 5.30; N, 10.52; S,
12.04; found: C, 54.15; H, 5.54; N, 10.29; S, 12.10%.
3.20 | Ethyl 6-methyl-4-phenyl-2-thioxo-
1,2,3,4-tetrahydropyrimidine-
5-carboxylate (7a)
3.17 | Ethyl 6-methyl-2-oxo-4-(p-tolyl)-
1,2,3,4-tetrahydropyrimidine-
5-carboxylate (6c)
Yellow solid; mp 209–210ꢀC (Lit. 209–210ꢀC[27]). FT-IR
(KBr, disk) ν: 3,325, 3,172, 3,099, 1,982, 1,660, 1,573, 1,465,
1,327, 1,280, 1,176, 1,119, 740, 695 cm−1. 1H NMR
(400 MHz, DMSO-d6, ppm) δ: 11.01 (s, 1H, NH), 9.62 (s,
1H, NH), 7.46–7.20 (m, 5H, ArH), 5.20 (d, J = 3.6 Hz, 1H,
CH), 4.00 (q, J = 7.0 Hz, 2H, OCH2), 2.31 (s, 3H, CH3), 1.11
(t, J = 3.4 Hz, 3H, CH3). 13C NMR (100 MHz, DMSO-d6,
ppm) δ: 174.70, 165.60, 145.52, 142.99, 129.03, 128.15,
126.86, 100.62, 60.06, 54.52, 17.63, 14.47; MS (EI): m/z (%)
276. Anal. Calcd for C14H16N2O2S: C, 60.58; H, 5.84; N,
10.14; S, 11.60; found: C, 60.60; H, 5.84; N, 10.20; S, 12.10%.
White solid; mp 214–216ꢀC (Lit. 214–216ꢀC[27]). (KBr,
disk) ν: 3,250, 3,111, 2,961, 1,723, 1,704, 1,655, 1,460,
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1,309, 1,286, 1,220, 1,088, 780 cm−1. H NMR (400 MHz,
DMSO-d6, ppm) δ: 10.0 (s, 1H, NH), 8.99 (s, 1H, NH),
7.50 (s, 4H, ArH), 5.10 (d, J = 2.6 Hz, 1H, CH), 3.90 (q,
J = 7.2 Hz, 2H, OCH2), 2.52 (s, 3H, CH3), 1.22 (t,
J = 7.2 Hz, 3H, CH3). 13C NMR (100 MHz, DMSO-d6,
ppm) δ: 165.0, 158.4, 152.1, 149.9, 137.1, 127.4, 113.6,
113.7, 99.6, 59.1, 55.2, 53.3, 19.0, 15.15; MS (EI): m/z (%)
274. Anal. Calcd for C15H18N2O3: C, 65.68; H, 6.61; N,
10.21; found: C, 65.68; H, 6.67; N, 10.48%.
3.21 | Ethyl 4-(4-chlorophenyl)-6-methyl-
2-thioxo-1,2,3,4-tetrahydropyrimidine-
5-carboxylate (7b)
3.18 | Ethyl 4-(4-methoxyphenyl)-
6-methyl-2-oxo-1,2,3,4-tetrahydro
pyrimidine-5-carboxylate (6d)
White solid; mp 198–200ꢀC (Lit. 196–198ꢀC[27]). 1H NMR
(400 MHz, DMSO-d6, ppm) δ 10.35 (s, 1H, NH), 9.64 (s,
1H, NH), 7.35–7.22 (m, 4H, ArH), 5.17 (d, J = 3.0 Hz, 1H,
CH), 4.01–3.96 (m, 2H, OCH2), 2.26 (s, 3H, CH3), 1.09 (t,
J = 7.2 Hz, 3H, CH3). 13C NMR (100 MHz, DMSO-d6,
ppm) δ: 176.7, 165.52, 145.92, 142.91, 132.80, 129.14,
128.85, 100.82, 61.00, 52.90, 17.72, 14.54. MS (EI): m/z
White solid; mp 200–203ꢀC (Lit. 201–202ꢀC[27]). FT-IR
(KBr) ν: 3,245.23, 3,112.55, 2,985.30, 1,727.42, 1,650.50,
1,461.28 cm−1 1H NMR (400 MHz, DMSO-d6, ppm)
.
δ: 9.20 (s, 1H, NH), 7.70 (s, 1H, NH), 7.13–6.90 (m,