9
02
E. Karim, K. Kishore and J. N. Vishwakarma
Vol. 40
EXPERIMENTAL
Melting points were determined on Thomas Hoover apparatus
1-Phenyl-3-(4-chlorophenyl)-5-(4-chlorobenzoyl)-6-methylthio-
1
,2,3,4-tetrhydropyrimidine (2d).
This compound was obtained as a white solid in 83% yield, mp
and are uncorrected. The reaction progress was monitored by tlc
on silica gel. The infrared spectra of the products were recorded
-1 1
1
81-182 °C; ir (KBr): 1616, 1591, 1547, 1489 cm ; H nmr
(
CCl ): δ 1.72 (s, 3H), 4.25 (s, 2H), 4.93 (s, 2H), 6.50-8.20 (m,
4
1
on Perkin Elmer 983 spectrophotometer and H nmr spectra on
13H).
Varian EM-390 spectrometer using TMS as internal standard.
Mass spectra were recorded on Jeol D-300 mass spectrometer,
while the 13C nmr spectra were obtained on a Brucker ACF-300
spectrometer. The starting materials, 1a-d, were prepared by the
reported procedure [14].
Anal. Calcd. for C H Cl N OS (455.40): C, 63.29; H, 4.43;
N, 6.15. Found: C, 63.06; H, 4.31; N, 5.99.
2
4
20
2 2
1-Phenyl-3-(4-methylphenyl)-5-(4-chlorobenzoyl)-6-
methylthio-1,2,3,4-tetrahydropyrimidine (2e).
1
1
-Aralkyl/aryl-3-alkyl/aralkyl/aryl-5-benzoyl-6-methylthio-
,2,3,4-tetrahydropyrimidines (2a-h).
This compound was obtained as a white solid in 81% yield, mp
-1 1
162-163 °C; ir (KBr): 1616, 1585, 1549, 1515, 1486 cm ; H
nmr (CCl ): δ 1.73 (s, 3H), 2.23 (s, 3H), 4.26 (s, 2H), 4.94 (s,
4
General Procedure.
2
H), 6.60-8.25 (m, 13H).
A mixture of primary amine (1 mmol) and formaldehyde (2
mmol, 40% solution) in 2 mL methanol was stirred at room tem-
perature for 5 minutes. To this was added a solution of N, S-
acetal 1 (1 mmol) in 4-5 mL methanol and the resulting mixture
was stirred at room temperature. A precipitate was observed after
Anal. Calcd. for C H ClN OS (434.98): C, 69.03; H, 5.33;
N, 6.44. Found: C, 69.31; H, 5.26; N, 6.39.
2
5
23
2
1
-Phenyl-3-(4-methoxyphenyl)-5-(4-chlorobenzoyl)-6-
methylthio-1,2,3,4-tetrahydropyrimidine (2f).
5
-10 minutes. After completion of the reaction (2-6 hours, moni-
This compound was obtained as a bright yellow solid in 91%
yield, mp 170-172 °C; ir (KBr): 1593, 1562, 1524, 1511 cm ; H
tored by tlc), the reaction mixture was cooled in ice and the pre-
cipitate was filtered, washed with cold methanol (3x1 mL) and
dried to give analytically pure 2a-h. These compounds were re-
crystallized from methanol.
-1 1
nmr (CCl ): δ 1.72 (s, 3H), 3.70 (s, 3H), 4.14 (s, 2H), 4.84 (s,
4
+
2
4
H), 6.60-6.80 (m, 4H), 6.90-8.10 (m, 9H); ms: m/z 452 (M +2,
.6%), 451 (M +1, 5.6%), 450 (M , 11.9%), 403 (28%), 268
+
+
(76.4%), 139 (100%).
1
-Benzyl-3-(4-methoxyphenyl)-5-benzoyl-6-methylthio-1,2,3,4-
Anal. Calcd. for C H ClN O S (450.98): C, 66.58; H, 5.14;
N, 6.21. Found: C, 66.25; H, 5.23; N, 6.30.
tetrahydropyrimidine (2a).
25 23
2 2
This compound was obtained as a white solid in 74% yield, mp
31-132 °C; ir (KBr): 1605, 1594, 1574, 1538, 1505 cm- ; H
1
1
1
1-Phenyl-3-ethyl-5-(4-chlorobenzoyl)-6-methythio-1,2,3,4-
nmr (CDCl ): δ 2.00 (s, 3H), 3.70 (s, 3H), 3.96 (s, 2H), 4.30 (s,
tetrahydropyrimidine (2g).
3
1
3
2H), 4.53 (s, 2H), 6.70-7.00 (m, 4H), 7.20-8.00 (m, 10H);
C
This compound was obtained as an off-white solid in 80%
yield, mp 129 °C; ir (KBr): 1608, 1587, 1532, 1487 cm ; H nmr
nmr (CDCl ): δ 16.41, 50.79, 54.93, 55.58, 67.50, 114.62,
3
-1 1
117.85, 118.94, 127.55, 128.00, 128.62, 128.84, 131.39, 137.79,
(
CCl ): δ 1.00 (t, 3H), 1.66 (s, 3H), 2.60 (q, 2H), 3.60 (s, 2H),
4
1
40.97, 142.18, 152.51, 153.91, 195.90.
Anal. Calcd. for C H N O S (430.56): C, 72.53; H, 6.09; N,
+
4
.25 (s, 2H), 7.00-8.02 (m, 9H); ms: m/z 374 (M +2, 0.5%), 373
2
6
26
2
2
+
+
(M +1, 1.3%), 372 (M , 5.2%), 267 (100%), 139 (85.6%).
6
.51. Found: C, 72.27; H, 6.15; N, 6.62.
Anal. Calcd. for C H ClN OS (372.91): C, 64.42; H, 5.67;
2
0
21
2
1
,3-Dibenzyl-5-(4-methylbenzoyl)-6-methylthio-1,2,3,4-tetrahy-
N, 7.51. Found: C, 64.70; H, 5.65; N, 7.64.
dropyrimidine (2b).
1
-Phenyl-3-methyl-5-(4-chlorobenzoyl)-6-methythio-1,2,3,4-
This compound was obtained as a white solid in 85% yield, mp
tetrahydropyrimidine (2h).
-1 1
1
30 °C; ir (KBr): 1627, 1601, 1558, 1491 cm ; H nmr (CDCl ):
3
This compound was obtained as an off-white solid in 71%
δ 2.01 (s, 3H), 2.40 (s, 3H), 3.48 (s, 2H), 3.59 (2s, each, 2H), 4.45
-1 1
yield, mp 126-127 °C; ir (KBr): 1608, 1587, 1533, 1488 cm ; H
nmr (CCl ): δ 1.66 (s, 3H), 2.36 (s, 3H), 3.50 (s, 2H), 4.20 (s,
1
3
(
s, 2H), 7.04-7.71 (m, 14H); C nmr (CDCl ): δ 16.37, 21.57,
3
4
5
1
1
4.70, 54.79, 58.08, 67.80, 96.02, 118.96, 127.08, 127.17,
27.83, 128.24, 128.35, 128.52, 128.79, 137.68, 137.85, 137.96,
41.66, 149.74, 195.27.
1
3
2
7
1
H), 7.00-8.00 (m, 9H); C nmr (CDCl ): δ 15.07, 41.59, 55.39,
3
5.05, 117.98, 125.32, 125.81, 128.28, 128.93, 129.82, 137.42,
39.48, 146.16, 146.93, 194.93.
Anal. Calcd. for C H N OS (428.59): C, 75.66; H, 6.58; N,
2
7 28 2
Anal. Calcd. for C H ClN OS (358.89): C, 63.59; H, 5.34,
1
9
19
2
6
1
.54. Found: C, 75.89; H, 6.50; N, 6.41.
N, 7.80. Found: C, 63.72; H, 5.40; N, 7.71.
-Phenyl-3-benzyl-5-(4-methoxybenzoyl)-6-methylthio-1,2,3,4-
tetrahydropyrimidine (2c).
Acknowledgement.
This compound was obtained as a white solid in 77% yield, mp
The authors wish to express their gratitude to Rev Fr Stephen
Mavely, SDB, Principal of the College for providing infra-struc-
tural facilities. Thanks are also due to Rev Fr J Nellanatt for
encouragement and help during the course of this invesigation.
Financial assistance from the UGC and NATP-ICAR is gratefully
acknowledged. We also thank the Heads of RSIC-CDRI
(Lucknow) and RSIC-NEHU (Shillong) for recording spectra.
28-129 °C; ir (KBr): 1615, 1592, 1541, 1496 cm- ; H nmr
1
1
1
(
4
(
CCl ): δ 1.70 (s, 3H), 3.60 (s, 2H), 3.70 (s, 2H), 3.80 (s, 3H),
4
+
.16 (s, 2H), 6.66-7.86 (m, 14H); ms: m/z 431 (M +1, 10%), 430
M , 13.8%), 385 (27.4%), 91 (100%).
+
Anal. Calcd. for C H N O S (430.56): C, 72.53; H, 6.09; N,
2
6 26 2 2
6
.51. Found: C, 72.81; H, 5.98; N, 6.60.