J = 2.0), 5.13 (d, 1H, J = 3.6), 4.03 (dq, 2H, J = 7.2, 3.2), 3.10 (s,
1H), 2.50–2.52 (m, 1H), 2.48 (s, 3H), 2.26 (s, 3H), 1.13 (t, J = 7.2,
3H). 13C NMR (100 MHz, d6-DMSO): dC 165.53, 153.06, 150.31,
141.03, 136.36, 128.88, 125.87, 102.51, 59.42, 51.96, 29.60, 20.55,
15.92, 13.98. Anal. Calcd for C16H20N2O3: C, 66.65; H, 6.99; N,
9.72. Found: C, 66.50; H, 7.11; N, 9.51%. Mp 107–111 ◦C.
J = 1.5, 4H), 5.12 (d, J = 3.3, 1H), 3.97 (q, J = 7.0, 2H), 2.63
(t, J = 7.3, 2H), 2.24 (s, 3H), 1.49–1.62 (m, 2H), 1.09 (t, J =
7.0, 3H), 0.90 (t, J = 7.1, 3H). 13C NMR (100 MHz, d6-DMSO):
dC 165.56, 152.86, 152.64, 142.47, 136.83, 129.36, 126.59, 99.66,
59.66, 54.08, 32.78, 22.10, 21.10, 14.50, 14.15. HRMS (FAB)◦Calcd
+
for [C17H23N2O3 ] 303.1709, Found 303.1701. Mp 140–144 C.
5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-6-methyl-4-(4-
5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-1-methyl-4-(4-
methylphenyl)-2-oxo-6-propyl-, ethyl ester (4j). (40% yield); H
1
1
methylphenyl)-2-thioxo-, ethyl ester (4d)21a
.
(>99%); H NMR
(400 MHz, d6-DMSO): dH 10.29 (s, 1H), 9.61 (br, 1H), 7.08–7.16
(m, 4H), 5.13 (d, J = 3.6, 1H), 4.00 (q, J = 7.2, 2H), 2.28 (s,
3H), 2.27 (s, 3H), 1.11 (t, J = 7.2, 3H). 13C NMR (100 MHz, d6-
DMSO): dC 173.66, 164.65, 144.36, 140.54, 136.38, 129.33, 127.82,
126.68, 125.02, 100.18, 78.47, 59.65, 53.43, 16.16, 12.92. HRMS
(FAB) Calcd for [C15H19N2O2S+] 291.1167, Found 291.1165. Mp
190–193 ◦C.
NMR (400 MHz, d6-DMSO/TMS): dH 7.97 (d, J = 3.6, 1H),
7.07–7.12 (m, 4H), 5.09 (d, J = 3.6, 1H), 3.99–4.07 (m, 2H), 3.10
(s, 3H), 2.81–2.90 (m, 2H), 2.51 (s, 3H), 2.25 (s, 3H), 1.45–1.56
(m, 2H), 1.13 (t, J = 7.2, 3H), 0.96 (t, J = 7.4, 3H). 13C NMR
(100 MHz, d6-DMSO/TMS): dC 165.13, 153.74, 153.30, 140.93,
136.32, 128.88, 125.82, 102.49, 59.43, 51.64, 30.21, 29.26, 21.53,
20.55, 13.96, 13.80. Anal. Calcd for C18H24N2O3: C, 68.33; H, 7.65;
N, 8.85. Found: C, 68.22; H, 7.60; N, 8.76%. Mp 140–141 ◦C.
5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-4-(4-chloro-
phenyl)-6-methyl-2-oxo-, ethyl ester (4e)5l. (87% yield); 1H NMR
(400 MHz, d6-DMSO/TMS): dH 9.26 (br, 1H), 7.79 (br, 1H), 7.40
(d, J = 8.2, 2H), 7.25 (d, J = 8.2, 2H), 5.14 (d, J = 3.2, 1H), 3.98
(q, J = 7.0, 2H), 2.25 (s, 3H), 1.09 (t, J = 7.0, 3H). 13C NMR
(100 MHz, d6-DMSO/TMS): dC 165.10, 151.83, 148.63, 143.67,
131.67, 128.30, 128.08, 98.69, 59.17, 53.28, 17.69, 13.96. Anal.
Calcd for C14H15ClN2O3: C, 57.05; H, 5.13; Cl, 12.03; N, 9.50.
Found: C, 57.00; H, 5.15; Cl, 11.93; N, 9.40%. Mp 214–217 ◦C.
5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-1,3-dimethyl-4-
(4-methylphenyl)-2-oxo-6-propyl-, ethyl ester (4k). Yellow oil.
(12% yield); 1H NMR (400 MHz, d6-DMSO/TMS): dH 7.11 (dd,
J = 8.4, 6.8, 4H), 5.15 (s, 1H), 4.02 (q, J = 7.2, 2H), 3.19 (s, 3H),
2.78–2.94 (m, 2H), 2.75 (s, 3H), 2.26 (s, 3H), 1.42–1.54 (m, 2H),
1.15 (t, J = 7.2, 3H), 0.95 (t, J = 7.2, 3H). 13C NMR (100 MHz, d6-
DMSO/TMS): dC 164.82, 152.86, 153.03, 137.91, 136.91, 129.08,
126.36, 102.39, 59.52, 59.42, 33.76, 30.19, 30.11, 21.41, 20.57,
+
13.92, 13.77. HRMS (FAB) Calcd for [C19H26N2NaO3 ] 353.1841,
Found 353.1851.
5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-6-ethyl-4-(4-
methylphenyl)-2-oxo-, ethyl ester (4f). (74% yield); 1H NMR
(400 MHz, d6-DMSO/TMS): dH 9.21 (br, 1H), 7.72 (br, 1H), 7.12
(br, 4H), 5.12 (d, J = 3.2, 1H), 3.98 (q, J = 7.2, 2H), 2.59–2.73 (m,
5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-4-(4-methyl-
phenyl)-6-propyl-2-thioxo-, ethyl ester (4l). (80% yield); 1H NMR
(400 MHz, d6-DMSO/TMS): dH 10.29 (s, 1H), 9.61 (br, 1H), 7.08–
7.16 (m, 4H), 5.13 (d, J = 3.6, 1H), 4.01 (q, J = 7.2, 2H), 2.68 (m,
2H), 2.26 (s, 3H), 1.54 (m, 2H), 1.10 (t, J = 7.2, 3H), 0.91 (t, J = 7.4,
3H). 13C NMR (100 MHz, d6-DMSO/TMS): dC 174.25, 164.81,
148.83, 140.51, 136.82, 128.98, 126.16, 100.52, 59.53, 53.57, 31.49,
21.70, 20.57, 13.87, 13.57. HRMS (FAB) Calcd for [C17H23N2O2S+]
319.1480, Found 319.1486. Mp 123–125 ◦C.
2H), 2.25 (s, 3H), 1.22 (t, J = 7.2, 3H), 1.10 (t, J = 7.2, 3H). 13
C
NMR (100 MHz, d6-DMSO/TMS): dC 164.95, 153.65, 152.49,
141.91, 136.37, 128.87, 126.11, 98.56, 59.17, 53.55, 24.05, 20.58,
13.95, 12.93. Anal. Calcd for C16H20N2O3: C, 66.65; H, 6.99; N,
9.72. Found: C, 66.36; H, 7.24; N, 9.55%. Mp 154–155 ◦C.
5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-4-(4-methoxy-
phenyl)-6-propyl-2-oxo-, ethyl ester (4g)6. (74% yield); 1H NMR
(400 MHz, d6-DMSO/TMS): dH 9.15 (br, 1H), 7.67 (br, 1H), 7.15
(d, J = 8.4, 2H), 6.88 (d, J = 8.8, 2H), 5.10 (br, 1H), 4.00 (q, J =
7.2, 2H), 3.72 (s, 3H), 2.60–2.64 (m, 2H), 1.48–1.56 (m, 2H), 1.11
(t, J = 7.2, 3H), 0.87 (t, J = 7.2, 3H). 13C NMR (100 MHz, d6-
DMSO/TMS): dC 165.09, 158.39, 152.36, 152.02, 137.00, 127.33,
113.65, 99.29, 59.18, 54.99, 53.27, 32.29, 21.63, 13.99, 13.66. Anal.
Calcd for C17H22N2O4: C, 64.13; H, 6.97; N, 8.80. Found: C, 63.66;
H, 6.81; N, 8.66%. Mp 120–124 ◦C.
5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-4-(4-chloro-
phenyl)-2-oxo-6-propyl-, ethyl ester (4m). (49% yield); 1H NMR
(400 MHz, d6-DMSO/TMS): dH 9.25 (br, 1H), 7.78 (br, 1H), 7.40
(d, 2H, J = 8.2), 7.25 (d, 2H, J = 8.2), 5.15 (d, J = 3.2, H1),
3.99 (q, J = 7.0, 2H), 2.63 (m, 2H), 1.58 (m, 2H), 1.10 (t, J = 7.0,
3H), 0.91 (t, J = 7.6, 3H). 13C NMR (100 MHz, d6-DMSO/TMS):
dC 164.87, 152.65, 152.10, 143.73, 131.71, 128.33, 128.05, 99.45,
98.55, 59.24, 53.30, 32.25, 21.57, 13.92, 13.60. Anal. Calcd for
C16H19ClN2O3: C, 59.54; H, 5.93; Cl, 10.98; N, 8.68. Found: C,
59.51; H, 6.15; Cl, 11.15; N, 8.61%. Mp 125–127 ◦C.
5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-4-(4-methoxy-
phenyl)-6-propyl-2-thioxo-, ethyl ester (4h). (86% yield); 1H
NMR (400 MHz, d6-DMSO/TMS): dH 10.30 (s, 1H), 9.61 (br,
1H), 7.03 (dd, J = 8.8, 86, 4H), 5.14 (d, J = 3.6, 1H), 4.01 (q,
J = 7.2, 2H), 3.72 (s, 3H), 2.67–2.72 (m, 2H), 1.48–1.59 (m,
2H), 1.13 (t, J = 7.2, 3H), 0.92 (t, J = 7.2, 3H). 13C NMR
(100 MHz, d6-DMSO/TMS): dC 174.18, 164.87, 158.69, 148.79,
135.66, 127.54, 113.80, 100.68, 59.55, 55.00, 53.35, 31.58, 21.78,
13.91, 13.63. HRMS (FAB) Calcd for [C17H23N2O3S+] 335.1429,
Found 335.1430. Mp 91–94 ◦C.
5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-4-(4-chloro-
phenyl)-6-propyl-2-thioxo-, ethyl ester (4n). (84% yield); 1H
NMR (400 MHz, d6-DMSO/TMS): dH 10.39 (br, 1H), 7.68 (br,
1H), 7.34 (dd, J = 8.4, 69.6, 4H), 5.19 (d, J = 3.6, 1H), 4.00–4.05
(m, 2H), 2.66–2.73 (m, 2H), 1.52–1.59 (m, 2H), 1.12 (t, J = 7.0,
3H), 0.91 (t, J = 7.0, 3H). 13C NMR (100 MHz, d6-DMSO/TMS):
dC 174.44, 164.68, 149.35, 142.34, 132.21, 128.53, 128.18, 100.06,
59.65, 53.32, 31.56, 21.74, 13.87, 13.60. HRMS (FAB) Calcd for
[C16H20ClN2O2S+] 339.0934, Found 339.0932. Mp 74–78 ◦C.
5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-4-(4-methyl-
1
phenyl)-2-oxo-6-propyl-, ethyl ester (4i). (72% yield) H NMR
5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-4-[(4-trifluoro-
(400 MHz, d6-DMSO): dH 9.14 (br, 1H), 7.68 (br, 1H), 7.11 (d,
methyl)phenyl]-6-propyl-2-oxo-, ethyl ester (4o). (37% yield); 1H
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The Royal Society of Chemistry 2010
Org. Biomol. Chem., 2010, 8, 1202–1211 | 1209
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