Paper
NJC
+
+
1
37.93, 139.43, 163.38, 164.69, 165.12; HRMS (ESI-MS): m/z [M + H]
calcd for C22 16ClN : 343.1002; found: 343.1005.
-(3-Chlorophenyl)-6-(4-fluorophenyl)-2-phenylpyrimidine (3h).
141.38, 163.40, 164.54, 164.92; HRMS (ESI-MS): m/z [M + H]
H
2
2
calcd for C23H18ClN : 357.1158; found: 357.1159.
4
4-(4-Bromophenyl)-2-phenyl-6-(p-tolyl)pyrimidine (3o). White
1
1
White solid; mp 166–168 1C; H NMR (400 MHz, CDCl ): d = 7.22– solid; mp 174–176 1C; H NMR (400 MHz, CDCl ): d = 2.46 (s,
3
3
7
.26 (m, 2H), 7.49–7.55 (m, 5H), 7.91 (s, 1H), 8.13 (d, J = 6.8 Hz, 3H), 7.36 (d, J = 8.0 Hz, 2H), 7.54 (m, 3H), 7.68 (d, J = 8.4 Hz, 2H),
13
13
1H), 8.27–8.31 (m, 3H), 8.69 (t, J = 2.8, 4.8 Hz, 2H); C NMR 7.93 (s, 1H), 8.17 (m, 4H), 8.70 (t, J = 2.0, 5.6 Hz, 2H); C NMR
): d = 109.92, 115.97, 116.18, 125.40, 127.47, (100 MHz, CDCl ): d = 21.59, 109.62, 125.38, 127.25, 128.52,
(100 MHz, CDCl
3
3
1
28.53, 128.59, 129.37, 129.46, 130.25, 130.86, 130.97, 133.44, 128.84, 129.74, 130.77, 132.14, 134.56, 136.56, 138.10, 141.39,
+
135.18, 137.79, 139.30, 163.47, 163.97, 164.69; HRMS (ESI-MS): 163.46, 164.55, 164.94; HRMS (ESI-MS): m/z [M + H] calcd for
+
m/z [M + H] calcd for C22
2
H15ClFN : 361.0908; found: 361.0917.
23 2
C H18BrN : 401.0653; found: 401.0652.
4
-(2-Chlorophenyl)-6-(3-chlorophenyl)-2-phenylpyrimidine (3i).
4-Methyl-2-phenyl-5H-chromeno[4,3-d]pyrimidin-5-one (3p).
1
1
White solid; mp 142–144 1C; H NMR (400 MHz, CDCl ): d = 7.44– Yellow solid; mp 254–256 1C; H NMR (300 MHz, DMSO-d ): d =
3
6
7
.54 (m, 8H), 7.85 (t, J = 2.4, 6.0 Hz, 1H), 7.99 (s, 1H), 8.12 (d, J = 2.30 (s, 3H), 6.68 (t, J = 7.5, 7.2 Hz, 1H), 6.80 (d, J = 7.8 Hz, 1H),
13
6.8 Hz, 1H), 8.29 (s, 1H), 8.66 (d, J = 4.0 Hz, 2H); C NMR 6.92 (d, J = 6.9 Hz, 1H), 7.00 (t, J = 7.2, 6.9 Hz, 1H), 7.49–7.59 (m,
1
3
(100 MHz, CDCl
3
): d = 115.26, 125.50, 127.36, 127.58, 128.56, 3H), 8.08 (d, J = 6.9 Hz, 2H); C NMR (75 MHz, DMSO-d
6
): d =
1
1
28.62, 130.27, 130.61, 130.91, 130.97, 131.77, 132.48, 135.22, 24.73, 115.34, 119.09, 120.72, 125.44, 127.08, 127.64, 128.66,
37.38, 137.72, 139.16, 162.52, 164.83, 165.09; HRMS (ESI-MS): 128.82, 131.44, 132.42, 153.91, 155.14, 164.18; HRMS (ESI-MS):
+
+
m/z [M + H] calcd for C22
H15Cl
2
N
2
: 377.0612; found: 377.0621.
13 2 2
m/z [M + H] calcd for C18H N O : 289.0977; found: 289.0991.
4
-(3-Chlorophenyl)-6-(4-chlorophenyl)-2-phenylpyrimidine (3j).
4-Methyl-2-phenyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)pyrimidine
1
1
White solid; mp 140–142 1C; H NMR (400 MHz, CDCl ): d = (3q). White solid; mp 74–76 1C; H NMR (300 MHz, CDCl ): d = 1.08
3
3
13
7
.50–7.53 (m, 7H), 7.87 (s, 1H), 8.10–8.24 (m, 4H), 8.67 (s, 2H);
NMR (100 MHz, CDCl
29.24, 130.23, 130.90, 131.01, 135.18, 135.67, 137.25, 137.71, 8.49 (m, 2H); C NMR (75 MHz, CDCl
C
(s, 6H), 1.43 (s, 3H), 1.57–1.61 (m, 2H), 1.75–1.83 (m, 2H), 2.10 (t, J =
3
): d = 109.93, 125.39, 127.45, 128.53, 128.61, 6.6, 6.0 Hz, 2H), 2.58 (s, 3H), 6.83 (s, 1H), 7.44–7.48 (m, 3H), 8.44–
13
1
1
3
): d = 19.27, 21.29, 24.45,
39.18, 163.51, 163.79, 164.69; HRMS (ESI-MS): m/z [M + H] calcd 28.93, 32.00, 34.35, 39.47, 120.18, 128.47, 128.49, 128.75, 130.31,
for C22 : 377.0612; found: 377.0623. 131.21, 138.50, 139.28, 163.98, 166.10, 168.79; HRMS (ESI-MS): m/z
-(4-Bromophenyl)-6-(3-chlorophenyl)-2-phenylpyrimidine (3k). [M + H] calcd for C20
+
H15Cl N
2 2
+
4
H
25
N
2
: 293.2017; found: 293.2068.
4,6-Dimethyl-2-phenylpyrimidine (3r). White solid; mp 82–84 1C;
H NMR (400 MHz, CDCl ): d = 2.51 (s, 6H), 6.89 (s, 1H), 7.42–7.47
1
White solid; mp 130–132 1C; H NMR (400 MHz, CDCl ): d = 7.49–
.55 (m, 5H), 7.68 (d, J = 8.4 Hz, 2H), 7.91 (s, 1H), 8.12–8.16 (m,
H), 8.26 (s, 1H), 8.68 (t, J = 3.2, 4.4 Hz, 2H); C NMR (100 MHz, (m, 3H), 8.40–8.43 (m, 2H); C NMR (100 MHz, CDCl ): d 24.06,
3
1
7
3
3
13
13
3
CDCl
3
): d = 109.97, 125.41, 125.72, 127.48, 128.54, 128.61, 128.86, 117.85, 128.12, 128.34, 130.16, 138.05, 164.08, 166.65; HRMS
+
130.26, 130.92, 131.03, 132.24, 135.20, 136.17, 137.71, 139.21, (ESI-MS): m/z [M + H] calcd for C12
H
13
N
2
: 185.1079; found: 185.1093.
+
1
C
63.62, 163.94, 164.77; HRMS (ESI-MS): m/z [M + H] calcd for
15BrClN : 421.0107; found: 421.0104.
-(4-Fluorophenyl)-2-phenyl-6-(p-tolyl)pyrimidine (3l). White 6H), 2.54 (s, 3H), 2.96–3.03 (m, 1H), 6.90 (s, 1H), 7.45 (m, 3H),
4-Isopropyl-6-methyl-2-phenylpyrimidine (3s). White solid;
mp 102–104 1C; H NMR (400 MHz, CDCl ): d 1.33 (d, J = 6.8 Hz,
3
1
22
H
4
2
1
13
solid; mp 150–152 1C; H NMR (400 MHz, CDCl ): d = 2.46 (s, 8.46 (d, J = 7.2 Hz, 2H); C NMR (100 MHz, CDCl ): d 21.73,
3
3
3
7
H), 7.24 (distorted t, J = 8.4 Hz, 2H), 7.36 (d, J = 7.6 Hz, 2H), 24.26, 35.82, 115.22, 128.16, 128.28, 130.07, 138.29, 163.79,
+
.54 (m, 3H), 7.92 (s, 1H), 8.19 (d, J = 7.6 Hz, 2H), 8.27–8.31 166.83, 175.22; HRMS (ESI-MS): m/z [M + H] calcd for
1
3
(distorted q, J = 1.6, 6.0 Hz, 2H), 8.71 (d, J = 6.0 Hz, 2H);
C
14 17 2
C H N : 213.1392; found: 213.1398.
3
NMR (100 MHz, CDCl ): d = 21.57, 109.58, 115.86, 116.08,
1
1
27.24, 128.51, 129.30, 129.39, 129.73, 130.72, 133.79, 134.65,
Acknowledgements
38.18, 141.32, 163.36, 164.48, 164.81; HRMS (ESI-MS): m/z
+
[M + H] calcd for C23
2
H18FN : 341.1454; found: 341.1458.
This work was supported by CSIR-New Delhi (pool scheme no.
4
-(2-Chlorophenyl)-2-phenyl-6-(p-tolyl)pyrimidine (3m). White
8644-A, sanction no. 01(2427)/10/EMR-II dated 28/12/2010).
1
solid; mp 124–126 1C; H NMR (400 MHz, CDCl ): d = 2.46 (s, 3H),
3
K.S.V. and H.P.K thank UGC-SAP and CSIR-New Delhi, respec-
tively, for award of Senior Research Fellowships. The authors
thank Prof. P. M. Bhate for his generous support.
7.36 (d, J = 7.6 Hz, 2H), 7.43–7.56 (m, 6H), 7.85 (t, J = 2.0, 6.8 Hz,
1
H), 7.99 (s, 1H), 8.19 (d, J = 8.0 Hz, 2H), 8.68 (t, J = 1.6, 5.2 Hz, 2H);
13
C NMR (100 MHz, CDCl
28.53, 129.76, 130.56, 130.68, 130.71, 131.76, 132.50, 134.52,
37.73, 138.12, 141.37, 163.90, 164.61; HRMS (ESI-MS): m/z
3
): d = 21.59, 114.89, 127.29, 127.36,
1
1
References
+
[M + H] calcd for C23
2
H18ClN : 357.1158; found: 357.1152.
4
-(4-Chlorophenyl)-2-phenyl-6-(p-tolyl)pyrimidine (3n). White
1 K. Undheim and T. Benneche, in Comprehensive Heterocyclic
Chemistry II, ed. A. R. Katritzky, C. W. Rees and E. V. F. Scriven,
Pergamon Press, London, 1996, ch. 2, vol. 6, pp. 93–231.
2 D. J. Brown, R. F. Evans and W. B. Cowden, in The Pyrimidines,
ed. E. C. Taylor and A. Weissberger, John Wiley, New York,
1994, vol. 52.
1
solid; mp 166–168 1C; H NMR (400 MHz, CDCl ): d = 2.46
s, 3H), 7.36 (d, J = 8.0 Hz, 2H), 7.53 (m, 5H), 7.93 (s, 1H), 8.20
dd, J = 8.0, 8.4 Hz, 4H), 8.70 (d, J = 6.0 Hz, 2H); C NMR
100 MHz, CDCl ): d = 21.58, 109.66, 127.25, 128.51, 128.53,
28.61, 129.18, 129.74, 130.76, 134.58, 136.10, 136.94, 138.12,
3
(
(
(
1
3
3
1
New J. Chem.
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