9732
P. Shanmugam, P. T. Perumal / Tetrahedron 62 (2006) 9726–9734
Anal. calcd for C H N O : C, 71.84; H, 5.43; N, 8.38.
2
Found: C, 71.76; H, 5.21; N, 8.73.
3.73 (s, 3H), 3.92 (q, J¼6.8 Hz, 2H), 6.77 (d, J¼9.2 Hz,
0 18 2 3
1
3
2H), 7.4 (d, J¼9.2 Hz, 2H). C NMR: d 13.6, 18.1, 33.1,
55.4, 61.8, 111.5, 113.7, 129.8, 130.3, 155.9, 158.4, 161.7,
167.3, 169.8. EIMS (m/z): 302 (M ). Anal. calcd for
+
3.3.4.3. Ethyl 6-methyl-4-(2-chlorophenyl)-pyrimidin-
(1H)-one-5-carboxylate (2k). Mp: 164–166 C. IR (KBr):
ꢀ
106, 1422, 1505, 1658, 1713, 1732, 2827, 3147,
2
1
3
(
(
C H N O : C, 63.56; H, 6.00; N, 9.27. Found: C, 63.44;
1
6 18 2 4
H, 5.92; N, 9.31.
ꢁ
1
1
345 cm
.
H NMR: d 0.69 (t, J¼6.8 Hz, 3H), 2.49
s, 3H), 3.80 (q, J¼6.8 Hz, 2H), 7.37–7.45 (m, 4H), 11.53
3.3.4.9. Ethyl 6-methyl-4-(4-methoxyphenyl)-pyrimi-
din-2(1H)-one-5-carboxylate (2i). Mp: 172–173 C. IR
1
3
ꢀ
H NMR:
s, 1H, NH). C NMR: d 13.6, 19.1, 60.9, 109.5, 127.5,
ꢁ
1
1
1
1
29.4, 129.7, 130.0, 130.7, 140.1, 155.3, 162.5, 164.7,
72.1. EIMS (m/z): 292 (M ). Anal. calcd for
(KBr): 1132, 1463, 1643, 1693, 3220 cm
.
+
d 0.9 (t, J¼6.5 Hz, 3H), 2.3 (s, 3H), 3.81 (s, 3H), 3.93 (q,
C H ClN O : C, 57.44; H, 4.48; N, 9.57. Found: C,
1
J¼6.8 Hz, 2H), 6.8 (m, 2H), 7.2 (t, J¼8.4 Hz, 2H), 9.7 (s,
4
13
2 3
1
3
5
7.32; H, 4.42; N, 9.55.
1H). C NMR: d 13.8, 21.1, 55.2, 61.4, 102.6, 114.8,
1
18.7, 128.5, 129.9, 146.5, 157.7, 160.1, 172.1. EIMS
(m/z): 288 (M ). Anal. calcd for C H N O : C, 62.49; H,
15 16 2 4
+
3.3.4.4. Ethyl 6-methyl-4-(2-nitrophenyl)-pyrimidin-
(1H)-one-5-carboxylate (2c). Mp: 180–182 C. IR
ꢀ
KBr): 1208, 1421, 1543, 1641, 1693, 1715, 2827,
2
(
5.59; N, 9.72. Found: C, 62.35; H, 5.52; N, 9.70.
ꢁ
1 1
3
3
345 cm . H NMR: d 0.67 (t, J¼7.5 Hz, 3H), 2.49 (s,
3.3.4.10. Ethyl 6-methyl-4-(2-propyl)-pyrimidin-2(1H)-
one-5-carboxylate (4a). Mp: 232–234 C. IR (KBr):
ꢀ
1131, 1455, 1642, 1688, 3205, 3433 cm
H), 3.78 (q, J¼7.5 Hz, 2H), 7.40 (d, J¼7.5 Hz, 1H), 7.67
ꢁ
1
1
(
t, J¼7.5 Hz, 1H), 7.77 (t, J¼7.5 Hz, 1H), 8.17 (d, J¼
.
H NMR:
1
3
8
6
1
.1 Hz, 1H), 11.50 (s, 1H, NH). C NMR: d 13.7, 20.5,
1.0, 107.5, 124.6, 129.7, 130.5, 134.05, 134.7, 146.6,
d 1.34 (t, J¼7.5 Hz, 3H), 1.39 (d, J¼6.8 Hz, 6H), 2.45
13
(s, 3H), 3.15 (m, J¼6.8 Hz, 1H), 4.32 (q, J¼7.5 Hz, 2H),
+
52.3, 162.2, 164.3, 173.3. EIMS (m/z): 303 (M ). Anal.
13.65 (s, 1H). C NMR: d 14.2, 21.1, 29.7, 61.9, 112.5,
145.6, 159.6, 163.1, 173.6. EIMS (m/z): 224 (M ). Anal.
+
calcd for C H N O : C, 55.45; H, 4.32; N, 13.86. Found:
1
4 13 3 5
C, 55.32; H, 4.27; N, 13.74.
calcd for C H N O : C, 58.91; H, 7.19; N, 12.49. Found:
1
1 16 2 3
C, 58.68; H, 7.12; N, 12.42.
3.3.4.5. Ethyl 6-methyl-4-(3-hydroxyphenyl)-pyrimi-
din-2(1H)-one-5-carboxylate (2l). Mp: 180–182 C. IR
ꢀ
ꢁ
3.3.4.11. Ethyl 4-(4-methoxyphenyl)-6-phenyl-pyrimi-
din-2(1H)-one-5-carboxylate (4b). Mp: 153–154 C. IR
1
1
ꢀ
(KBr): 1163, 1238, 1328, 1446, 1517, 1599, 1668, 1709,
(
KBr): 1132, 1463, 1643, 1693, 3204, 3421 cm
.
H
NMR: d 0.82 (t, J¼6.5 Hz, 3H), 2.4 (s, 3H), 3.9 (q,
ꢁ
1
1
J¼6.5 Hz, 2H), 6.8 (m, 3H), 7.2 (t, 7.5 Hz, 1H), 9.7 (s, 1H),
2280, 2808, 2984, 3213 cm
.
H NMR: d 0.85 (t,
1
3
1
1
1
1.32 (s, 1H). C NMR: d 13.8, 21.1, 61.4, 102.6, 114.8,
17.7, 118.7, 128.5, 129.9, 146.5, 157.7, 160.1, 163.2,
J¼6.8 Hz, 3H), 3.82 (s, 3H), 3.90 (q, J¼6.8 Hz, 2H), 6.94
(d, J¼9.2 Hz, 1H), 7.00 (d, J¼8.5 Hz, 1H), 7.40 (m, J¼6.9
and 7.6 Hz, 2H), 7.49 (d, J¼3.8 Hz, 1H), 7.58 (t,
J¼8.5 Hz, 2H), 8.01 (q, J¼8.5 and 9.2 Hz, 2H), 13.32
+
72.4. EIMS (m/z): 274 (M ). Anal. calcd for C H N O :
1
4 14 2 4
C, 61.31; H, 5.14; N, 10.21. Found: C, 61.28; H, 5.16; N,
0.20.
1
3
1
(s, 1H, D O-exchangeable). C NMR: d 13.5, 55.4, 61.9,
2
1
150.2, 158.2, 162.2, 162.9, 174.1. EIMS (m/z): 350 (M ).
06.5, 114.2, 128.6, 129.2, 129.6, 130.2, 138.5, 139.7,
+
3.3.4.6. Methyl 6-methyl-4-(4-methoxyphenyl)-pyri-
midin-2(1H)-one-5-carboxylate (2m). Mp: 180–181 C.
ꢀ
IR (KBr): 1228, 1456, 1547, 1660, 1681, 1715, 2827,
Anal. calcd for C H N O : C, 68.56; H, 5.18; N, 8.00.
2
0 18 2 4
Found: C, 68.49; H, 5.12; N, 8.02.
ꢁ
1 1
3
3
(
348 cm . H NMR: d 2.32 (s, 3H), 3.57 (s, 3H), 3.77 (s,
H), 6.97 (d, J¼8.4 Hz, 2H), 7.40 (d, J¼8.4 Hz, 2H), 12.23
3.3.4.12. Ethyl 4-(4-methoxyphenyl)-6-trifluoro-
methyl-pyrimidin-2(1H)-one-5-carboxylate (4c). Mp:
1
3
s, 1H, D O-exchangeable). C NMR: d 19.2, 52.6, 55.9,
2
ꢀ
1
1
02.3, 114.3, 116.4, 130.0, 136.1, 156.3, 161.7, 167.4,
74.2. EIMS (m/z): 274 (M ). Anal. calcd for C H N O :
136–138 C. IR (KBr): 1017, 1127, 1162, 1210, 1299,
+
ꢁ1
1
1509, 1605, 1699, 1739, 3188 cm . H NMR: d 1.15 (t,
J¼6.8 Hz, 3H), 3.85 (s, 3H), 4.17 (q, J¼6.8 Hz, 2H), 7.05
(d, J¼8.4 Hz, 2H), 7.54 (d, J¼8.4 Hz, 2H), 11.50 (s, 1H).
1
4 14 2 4
C, 61.31; H, 5.14; N, 10.21. Found: C, 61.28; H, 5.08;
N, 10.13.
1
3
C NMR: d 13.7, 55.6, 62.8, 109.5, 114.9, 122.0 (q,
3.3.4.7. Ethyl 1,6-dimethyl-4-phenyl-pyrimidin-2(1H)-
one-5-carboxylate (2n). Mp: 212–213 C. IR (KBr): 1103,
J¼275 Hz), 130.2, 138.6, 155.6 (q, J¼34 Hz), 161.2,
ꢀ
197, 1286, 1439, 1494, 1616, 1679, 1722, 2990 cm
+
163.2, 164.1, 174.2. EIMS (m/z): 342 (M ). Anal. calcd for
C H F N O : C, 52.64; H, 3.83; N, 8.18. Found: C,
52.59; H, 3.77; N, 8.19.
ꢁ
1
1
.
1
5 13 3 2 4
1
H NMR: d 1.14 (t, J¼7.6 Hz, 3H, CH CH ), 2.41 (s, 3H),
3
2
3
.35 (s, 3H, N-Me), 3.97 (q, J¼7.6 Hz, 2H, CH CH ), 7.38
3
2
(
t, J¼6.8 Hz, 2H), 7.41 (t, J¼7.6 and 2.3 Hz, 1H), 7.54 (t,
3.3.4.13. Ethyl 6-bromomethyl-4-phenyl-pyrimidin-
2(1H)-one-5-carboxylate (4d). Mp: 181–182 C. IR
1
3
ꢀ
(KBr): 1125, 1468, 1651, 1689, 3253, 3455 cm
J¼6.9 Hz, 2H). C NMR: d 13.8, 20.2, 39.3, 61.0, 108.8,
ꢁ1
1
127.9, 128.6, 130.5, 137.1, 153.1, 155.3, 163.5, 173.5.
EIMS (m/z): 272 (M ). Anal. calcd for C H N O : C,
.
H
+
NMR: d 0.86 (t, J¼7.5 Hz, 3H), 3.84 (s, 2H, CH Br), 3.93
1
5
16
2
3
2
6
6.16; H, 5.92; N, 10.29. Found: C, 66.08; H, 5.83; N, 10.17.
(q, J¼7.5 Hz, 2H), 7.42 (m, 2H), 7.59 (t, J¼6.8 Hz, 3H),
1
3
1
25.9, 55.5, 105.3, 128.1, 128.7, 130.2, 140.5, 158.1, 162.3,
3.52 (s, 1H, D O-exchangeable, NH). C NMR: d 13.5,
2
3.3.4.8. Ethyl 1,6-dimethyl-4-(4-methoxyphenyl)-pyri-
midin-2(1H)-one-5-carboxylate (2o). Mp: 140–142 C. IR
ꢀ
+
166.8, 173.1. EIMS (m/z): 337 (M ). Anal. calcd for
C H BrN O : C, 49.87; H, 3.89; N, 8.31. Found: C,
49.78; H, 3.92; N, 8.27.
ꢁ
1 1
(
KBr): 1231, 1453, 1549, 1662, 1683, 1720, 3351 cm . H
1
4
13
2 3
NMR: d 0.85 (t, J¼6.7 Hz, 3H), 2.38 (s, 3H), 3.46 (s, 3H),