JOURNAL OF THE CHINESE
CHEMICAL SOCIETY
4
-Dihydropyrimidin-2(1H)-ones: Solvent-Free Method
1
s, 3H); C NMR (100 MHz, CDCl
3
(
3
+DMSO-d
6
) d 171.0, 157.8,
CDCl
3
+DMSO-d
6
) d 171.2, 161.4, 158.0, 152.3, 140.2, 132.4,
+
1
53.1, 149.6, 133.2, 132.2, 131.3, 104.6, 59.3, 55.6, 23.0; MS
120.1, 105.2, 58.9, 55.6, 23.0; MS (ESI): m/z 263 (M+H) . Ethyl
1,2,3,4-tetrahydro-4-(2-hydroxyphenyl)-6-methyl-2-oxopyr-
imidine-5-carboxylate (4o): Light yellow solid, m.p. 202-203
+
ESI): m/z 247 (M+H) . 5-Acetyl-3,4-dihydro-6-methyl-4-
(
phenylpyrimidin-2(1H)-one (4c): White solid, m.p. 232-234
-
C; IR (KBr, cm ) 3350 (NH), 3270 (NH), 3038 (Ar-CH), 2932
1
-1
°C; IR (KBr, cm ) 3564 (OH), 3380 (NH), 3245 (NH), 3053
°
1
alkyl-CH), 1699 (C=O), 1690 (C=O); H NMR (400 MHz,
(
(Ar-CH), 2995 (alkyl-CH), 1707 (C=O), 1651 (C=O), 1230 (O-
1
); H NMR (400 MHz, CDCl
DMSO-d
6
) d 9.15 (s, 1H), 7.80 (s, 1H), 7.34-7.22 (m, 5H), 5.25 (d,
CO), 1085 (O-CH
2
CH
3
3
+DMSO-d
6
)
1
3
J = 3.6 Hz, 1H), 2.28 (s, 1H), 2.10 (s, 3H); C NMR (100 MHz,
d 8.80 (s, 1H), 7.65 (s, 1H), 7.62-6.72 (m, 4H), 6.32 (s, 1H), 5.62
CDCl +DMSO-d ) d 199.5, 157.4, 152.9, 149.0, 133.4, 132.3,
+
31.5, 114.5, 59.5, 35.1, 24.0; MS (ESI): m/z 231 (M+H) .
3
6
(s, 1H), 4.04 (q, J = 7.06 Hz, 2H), 2.39 (s, 3H), 1.12 (t, J = 7.0 Hz,
13
3H); C NMR (100 MHz, CDCl +DMSO-d ) d 170.9, 159.5,
3 6
1
Methyl 1,2,3,4-tetrahydro-4-(4-methoxyphenyl)-6-methyl-2-
158.1, 153.7, 134.0, 133.2, 131.5, 123.9, 120.5, 102.7, 64.3, 54.5,
+
23.2, 19.0; MS (ESI): m/z 277 (M+H) . Ethyl 1,2,3,4-tetra-
oxopyrimidine-5-carboxylate (4d): Offwhite solid, m.p. 193-
-
95 °C; IR (KBr, cm ) 3489 (NH), 3246 (NH), 3072 (Ar-CH),
1
1
2
hydro-6-methyl-2-oxo-4-p-tolylpyrimidine-5-carboxylate
-
(4q): White solid, m.p. 169-170 °C; IR (KBr, cm ) 3325 (NH),
1
952 (alkyl-CH), 1712 (C=O), 1659 (C=O), 1241 (O-CO), 1102
1
); H NMR (400 MHz, CDCl
(
O-CH
3
3
) d 8.60 (s, 1H), 7.34 (s, 1H),
3245 (NH), 3028 (Ar-CH), 2981 (alkyl-CH), 1723 (C=O), 1705
1
7
.17-7.15 (d, J = 8.0 Hz, 2H), 6.75-6.73 (d, J = 8.4 Hz, 2H), 5.22
(C=O), 1222 (O-CO), 1089 (O-CH
DMSO-d
2.8 Hz, 1H), 3.96 (q, J = 6.8 Hz, 2H), 2.24 (s, 3H), 2.22 (s, 3H),
2
CH
3
); H NMR (400 MHz,
1
3
(
s, 1H), 3.70 (s, 3H), 3.53 (s, 3H), 2.26 (s, 3H); C NMR (100
MHz, CDCl +DMSO-d ) d 171.1, 163.6, 158.2, 152.2, 141.4,
32.4, 118.5, 105.3, 59.9, 59.1, 55.4, 23.1; MS (ESI): m/z 278
6
) d 9.16 (s, 1H), 7.69 (s, 1H), 7.10 (s, 4H), 5.08 (d, J =
3
6
1
3
1
6
1.08 (t, J = 7.0 Hz, 3H); C NMR (100 MHz, DMSO-d ) d 165.3,
+
M+H) . Ethyl 1,2,3,4-tetrahydro-4-(4-methoxyphenyl)-6-
(
152.1, 148.0, 141.0, 136.3, 128.8, 128.5, 126.0, 125.8, 99.3, 59.1,
+
53.5, 20.5, 17.7,14.0; MS (ESI): m/z 275 (M+H) .
methyl-2-oxopyrimidine-5-carboxylate (4e): Offwhite solid,
-
m.p. 200-203 °C; IR (KBr, cm ) 3324 (NH), 3224 (NH), 3042
1
(
(
(
Ar-CH), 2948 (alkyl-CH), 1705 (C=O), 1673 (C=O), 1210
1
); H NMR (400 MHz, CDCl
ACKNOWLEDGEMENTS
O-CO), 1185 (O-CH
2
CH
3
3
) d 7.97
The authors gratefully acknowledge SAIF (NEHU,
Shillong and CDRI, Lucknow) for the spectral analyses. C.
Kathing acknowledges the financial assistance provided by
UGC (RGNF).
s, 1H), 7.26 (s, 1H), 7.24-7.22 (d, J = 8.4 Hz, 2H), 6.84-6.82 (d, J
8.4 Hz, 2H), 5.35 (d, J = 2.0 Hz, 1H), 4.07 (q, J = 6.8 Hz, 2H),
=
1
3
3
.78 (s, 3H), 2.33 (s, 3H), 1.17 (t, J = 7.2 Hz, 3H); C NMR (100
MHz, CDCl +DMSO-d ) d 170.6, 163.5, 157.9, 152.3, 141.9,
32.5, 118.4, 105.2, 64.2, 59.9, 58.9, 23.0, 19.0; MS (ESI): m/z
3
6
REFERENCES
1
2
+
91 (M+H) . Methyl 1,2,3,4-tetrahydro-6-methyl-4-(4-nitro-
1. Hurst, E. W.; Hull, R. J. Med. Pharm. Chem. 1961, 3, 215.
2
3
. Ashok, M.; Holla, B. S.; Kumari, N. S. Eur. J. Med. Chem.
007, 42, 380.
phenyl)-2-oxopyrimidine-5-carboxylate (4j): Light Yellow
2
-
solid, m.p. 234-237 °C; IR (KBr, cm ) 3366 (NH), 3223 (NH),
1
. Atwal, K. S.; Swanson, B. N.; Unger, S. E.; Floyd, D. M.;
Moreland, S.; Hedberg, A.; O’Reilly, B. C. J. Med. Chem.
1991, 34, 806.
3
062 (Ar-CH), 2951 (alkyl-CH), 1729 (C=O), 1692 (C=O), 1223
1
); H NMR (400 MHz, CDCl
(
O-CO), 1096 (O-CH
3
3
+DMSO-d
6
)
4
. Grover, G. J.; Dzwonczyk, S.; McMullen, D. M.; Normandin,
D. E.; Parham, C. S.; Sleph, P. G.; Moreland, S. J. Cardio-
vasc. Pharmacol. 1995, 26, 289.
d 9.16 (s, 1H), 8.15-8.13 (d, J = 8.0 Hz, 2H), 7.59 (s, 1H),
7
3
1
.54-7.52 (d, J = 8.0 Hz, 2H), 5.40 (s, 1H), 3.60 (s, 1H), 2.34 (s,
1
3
3 6
H); C NMR (100 MHz, CDCl +DMSO-d ) d 170.7, 157.3,
5
6
. Kappe, C. O. Tetrahedron 1993, 49, 6937.
56.8, 154.4, 151.7, 132.5, 128.5, 103.3, 59.2, 58.8, 23.1; MS
. Rovnyak, G. C.; Kimball, S. D.; Beyer, B.; Cucinotta, G.;
Dimarco, D. J.; Gougoutas, J.; Hedberg, A.; Malley, M.; Mc-
Carthy, J. P.; Zhang, R.; Moreland, S. J. Med. Chem. 1995,
+
ESI): m/z 292 (M+H) . Methyl 1,2,3,4-tetrahydro-4-(4-hy-
(
droxyphenyl)-6-methyl-2-oxopyrimidine-5-carboxylate
-
4m): Offwhite Solid, m.p. 243-245 °C; IR (KBr, cm ) 3586
1
3
8, 119.
. Kappe, C. O.; Fabian, W. M. F.; Semones, M. A. Tetrahedron
997, 53, 2803.
(
7
8
(
OH), 3390 (NH), 3276 (NH), 3032 (Ar-CH), 2961 (alkyl-CH),
1
1
1
701 (C=O), 1683 (C=O), 1231 (O-CO), 1088 (O-CH
400 MHz, CDCl +DMSO-d
d, J = 8.4 Hz, 2H), 6.89 (s, 1H), 6.75-6.72 (d, J = 8.4 Hz, 2H),
3
); H NMR
. Atwal, K. S.; Rovnyak, G. C; Schwartz, J.; Moreland, S.;
Hedberg, A.; Gougoutas, J. Z.; Malley, M. F.; Floyd, D. M. J.
Med. Chem. 1990, 33, 2629.
(
3
6
) d 8.74 (s, 1H), 7.58 (s, 1H), 7.12
(
1
.22 (s, 1H), 3.59 (s, 3H), 2.31 (s, 3H); C NMR (100 MHz,
3
5
9. (a) Snider, B.; Chen, J.; Patil, A. D.; Freyer, A. Tetrahedron
J. Chin. Chem. Soc. 2014, 61, 1254-1258
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