RSC Advances
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DOI: 10.10R39S/CC4RAA0d7v3a34nGces
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NH), 9.25 (s, 1H, NH).13C NMR (100 MHz, DMSOꢀd6): δ 210 °C (lit. 207ꢀ208°C). H NMR (400 MHz, DMSOꢀd6): δ
14.4, 19.8, 54.3, 60.0, 100.5, 115.5, 129.4, 148.9, 156.2, 1.13 (t, J= 8.0 Hz, 3H, CH3), 2.51 (s, 3H, CH3),3.91(s,
161.0, 162.1, 166.8.
3H,OCH3), 4.06 (q, J= 7.6 Hz, 2H, CH2), 5.21(d, J= 2.8 Hz,
1H, CH), 6.82ꢀ7.17 (m, 4H, HꢀAro), 7.30 (s, 1H, NH), 9.52
3,4-Dihydro-5-etoxycarbonyl-4-(2-nitrophenyl)-6-methyl-
pyrimidine-2(1H)-one (4i):Whitepowder; mp 218ꢀ220 °C (s, 1H, NH). 13C NMR (100 MHz, DMSOꢀd6): δ 14.4, 19.5,
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(lit. 220ꢀ222°C). H NMR (400 MHz, DMSOꢀd6): δ 1.03 (t, 50.3, 50.7, 60.8, 100.9, 113.7, 113.9, 121.0, 139.9, 143.0,
J= 7.2 Hz, 3H, CH3), 2.32 (s, 3H, CH3),3.92 (q, J= 8.0Hz, 2H, 147.0, 153.9, 161.6, 167.5.
CH2), 5.51(s, 1H, CH), 6.90ꢀ7.30(m, 4H, HꢀAro), 7.82 (s, 1H,
3,4-Dihydro-5-etoxycarbonyl-4-(4-methoxyphenyl)-6-
NH), 9.17 (s, 1H, NH). 13C NMR (100 MHz, DMSOꢀd6): δ methyl-pyrimidine-2(1H)-one (4n):Whitepowder; mp 203ꢀ
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14.8, 17.3, 55.6, 60.8, 100.5, 112.9, 122.1, 130.7, 132.9, 205 °C (lit. 203ꢀ204°C). H NMR (400 MHz, DMSOꢀd6): δ
134.9, 151.4, 155.8, 161.4, 166.4.
1.14 (t, J= 7.2 Hz, 3H, CH3), 2.25 (s, 3H, CH3),2.90(s,
3H,OCH3), 3.46 (q, J= 7.6 Hz, 2H, CH2), 5.12(s, 1H, CH),
3,4-Dihydro-5-etoxycarbonyl-4-(3-nitrophenyl)-6-methyl-
pyrimidine-2(1H)-one (4j):Whitepowder; mp 225ꢀ227 °C 6.91 (d, J= 6.8 Hz, 2H, HꢀAro),7.19 (d, J= 6.8 Hz, 2H, Hꢀ
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(lit. 226ꢀ228°C). H NMR (400 MHz, DMSOꢀd6): δ 1.15 (t, Aro), 7.76 (s, 1H, NH), 9.12 (s, 1H, NH). 13C NMR (100
J= 8.0 Hz, 3H, CH3), 2.25 (s, 3H, CH3),4.04 (q, J= 8.0 Hz, MHz, DMSOꢀd6): δ 14.8, 18.8, 56.5, 57.8, 66.8, 100.6, 114.7,
2H, CH2), 5.17(d, J= 2.8 Hz, 1H, CH), 6.83ꢀ7.26(m, 4H, Hꢀ 127.6, 138.6, 148.2, 154.8, 158.8, 166.9.
Aro), 7.85 (s, 1H, NH), 9.22(s, 1H, NH). 13C NMR (100
3,4-Dihydro-5-etoxycarbonyl-4-(3,4-dimethoxyphenyl)-6-
MHz, DMSOꢀd6): δ 15.4, 17.9, 52.8, 59.4, 100.6, 113.7, methyl-pyrimidine-2(1H)-one (4o):Whitepowder; mp 176ꢀ
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121.8, 132.5, 142.4, 149.4, 149.9, 154.0, 161.6, 166.4.
3,4-Dihydro-5-etoxycarbonyl-4-(4-nitrophenyl)-6-methyl-
pyrimidine-2(1H)-one (4k):Whitepowder; mp 211ꢀ213 °C
178 °C (lit. 174ꢀ176°C). H NMR (400 MHz, DMSOꢀd6): δ
1.15 (t, J= 6.8 Hz, 3H, CH3), 2.30ꢀ2.31 (m, 6H, CH3,
OCH3),2.43 (s, 3H,OCH3),4.05 (q, J= 7.6 Hz, 2H, CH2),
5.26(d, J= 2.8 Hz, 1H, CH), 6.97ꢀ7.15 (m, 3H, HꢀAro), 7.89
(s, 1H, NH), 9.55 (s, 1H, NH). 13C NMR (100 MHz, DMSOꢀ
d6): δ 15.8, 21.0, 50.8, 56.3, 56.8,60.6, 100.6, 122.7, 128.9,
130.9, 136.8, 139.7, 144.9, 150.9, 154.4, 166.8.
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(lit. 208ꢀ211°C). H NMR (400 MHz, DMSOꢀd6): δ 1.13 (t,
J= 8.0 Hz, 3H, CH3), 2.30(s, 3H, CH3), 4.05 (q, J= 8.0 Hz,
2H, CH2), 5.35 (d, J= 2.8 Hz, 1H, CH), 7.36 (d, J= 7.2 Hz,
2H, HꢀAro), 7.93 (s, 1H, NH), 8.23 (d, J= 7.6 Hz, 2H, Hꢀ
Aro), 9.37 (s, 1H, NH).13C NMR (100 MHz, DMSOꢀd6): δ
14.9, 19.3, 55.2, 61.4, 100.5, 123.8, 124.7, 126.9, 142.6,
150.8, 154.9, 166.8.
3,4-Dihydro-5-etoxycarbonyl-4-(3-methoxy-4-
hydroxyphenyl)-6-methyl-pyrimidine-2(1H)-one
(4p):Whitepowder; mp 177ꢀ179 °C (lit. 173ꢀ175°C). 1H NMR
(400 MHz, DMSOꢀd6): δ 2.27 (s, 3H, CH3),3.55 (s, 3H,
CH3),3.76 (s, 3H, CH3),3.99 (q, J= 8.0 Hz, 2H, CH2), 5.06(d,
J= 2.8 Hz, 1H, CH), 6.73ꢀ6.86 (m, 3H, HꢀAro), 7.82 (s, 1H,
NH), 8.22 (s, 1H, NH). 13C NMR (100 MHz, DMSOꢀd6): δ
15.2, 18.9, 51.8, 56.8, 60.8, 100.3, 121.7, 128.9, 132.9, 136.7,
139.9, 144.9, 150.9, 152.1, 166.7.
3,4-Dihydro-5-etoxycarbonyl-4-(2-methoxyphenyl)-6-
methyl-pyrimidine-2(1H)-one (4l):Whitepowder; mp 258ꢀ
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260 °C (lit. 259ꢀ260°C). H NMR (400 MHz, DMSOꢀd6): δ
1.06 (t, J= 7.6 Hz, 3H, CH3), 2.25 (s, 3H, CH3),3.84(s,
3H,OCH3), 3.87(q, J= 6.8 Hz, 2H, CH2), 5.49(s, 1H, CH),
6.30 (s, 1H, NH),6.90ꢀ7.31(m, 4H, HꢀAro),9.15 (s, 1H, NH).
13C NMR (100 MHz, DMSOꢀd6): δ 14.9, 18.7, 43.6, 56.9,
59.4, 95.8, 112.3, 122.7, 129.7, 129.9, 131.8, 149.9, 151.8,
157.7, 166.8.
3,4-Dihydro-5-etoxycarbonyl-4-(4-trifluoromethylphenyl)-
6-methyl-pyrimidine-2(1H)-one (4q):Whitepowder; mp
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177ꢀ179 °C (lit. 173ꢀ175 °C). H NMR (400 MHz, DMSOꢀ
d6): δ 0.96 (t, J= 7.6 Hz, 3H, CH3), 2.51 (s, 3H, CH3),3.89 (q,
J= 7.6 Hz, 2H, CH2), 5.52(d, J= 2.8 Hz, 1H, CH), 7.27 (d, J=
3,4-Dihydro-5-etoxycarbonyl-4-(3-methoxyphenyl)-6-
methyl-pyrimidine-2(1H)-one (4m):Whitepowder; mp 208ꢀ
4 | RSC. Adv., 2014, 00, 1ꢀ11
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