An efficient synthesis of 4-naphthylpyrimidin-2-amine derivatives under solvent-free conditions

Article abstract of DOI:10.1002/jhet.839

A simple, efficient, and mild protocol for the synthesis of 4-naphthylpyrimidin-2-amine derivatives under solvent-free conditions by the reaction of aromatic aldehydes (or 1-naphthaldehyde), 2-acetylnaphthalene (or aromatic ketones), guanidine carbonate, and sodium hydroxide was reported. The advantages of this protocol include short reaction time, mild reaction conditions, easy workup, high yields, and environmental friendliness.

Full text of DOI:10.1002/jhet.839

696
An Efficient Synthesis of 4-Naphthylpyrimidin-2-amine
Vol 49
Derivatives under Solvent-Free Conditions
a,b
Liangce Rong,a,b Honglou Ji, Sheng Xia,a,b Shan Yin,a,b
*
Yanhui Shi,a,b and Shujiang Tu,a,b
aCollege of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, Jiangsu 221116, People’s
Republic of China
bJiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Xuzhou Normal University, Xuzhou,
Jiangsu 221116, People’s Republic of China
*
E-mail: lcrong2005@yahoo.com
Received September 21, 2010
DOI 10.1002/jhet.839
View this article online at wileyonlinelibrary.com.
A simple, efficient, and mild protocol for the synthesis of 4-naphthylpyrimidin-2-amine derivatives under
solvent-free conditions by the reaction of aromatic aldehydes (or 1-naphthaldehyde), 2-acetylnaphthalene (or
aromatic ketones), guanidine carbonate, and sodium hydroxide was reported. The advantages of this protocol
include short reaction time, mild reaction conditions, easy workup, high yields, and environmental friendliness.
J. Heterocyclic Chem., 49, 696 (2012).
INTRODUCTION
coworkers reported the synthesis of 2-amino-4-
(1-naphthyl)-6-arylpyrimidines by the three-step reaction,
which should undergo the process of acetylation, Claisen-
Schmidt Condensation, Michael addition, and cyclization
[15]. Because of its multistep process, the after-treatment
was very complex. In addition, the catalyst aluminum
chloride used in the acetylation must be anhydrous. In 2010,
Gopalakrishnan and coworkers reported the synthesis of 2-
morpholino-N-(4,6-diarylpyrimidin-2-yl)acetamides. In this
report, it not only suffered the similar drawbacks mentioned
above but also experienced long-reaction time [16]. On the
whole, most of these methods are associated with different
drawbacks such as long reaction time, low yields, strongly
alkalic conditions, use of toxic reagents, and the requirement
of an additional microwave oven. Hence, it is important to
develop a simple and convenient approach for the preparation
of pyrimidin-2-amine derivatives.
With the development of organic synthesis and environ-
mental concerns, developing a clean synthetic procedure has
become increasingly urgent. In this context, organic reactions
under solvent-free conditions are ideal protocols for the devel-
opment of environmental friendly and economical advanta-
geous chemical processes. Nowadays, there has been an
upsurge of interest in synthesizing compounds in solvent-free
environment [17–20]. When compared with the methods used
in the solvent, the solvent-free approach provided more advan-
tages such as higher yields, short reaction time, and easy
workup. Multicomponent reactions (MCRs) have proven
In recent years, pyrimidines and their derivatives have
received considerable attention in organic chemistry because
of their biological activities [1]. Substituted pyrimidines are
important compounds of drugs and other bioactive mole-
cules [2]. They display a wide range of pharmacological
activities [3–6]. For example, aminopyrimidine derivatives
have displayed interesting antibacterial, antitumor, and
HIV-I inhibiting activities [7]. Because of their interesting
activity as biological agents, considerable attention has been
focused on synthesizing this class of compounds.
The various methods of synthesis of aminopyrimidines were
reported [8–10]. 2-Aminopyrimidines were prepared previ-
ously by the reaction of substituted benzylideneacetophenones
with guanidine under reflux in ethanol [11,12]. In 2007,
Goswami et al. reported the synthesis of functionalized pyrimi-
dines with the microwave-expedited method. This method
involves column chromatography, which would consume a
lot of solvents and time that lead to a relatively low yields.
Meanwhile, it takes microwave as its reaction condition, which
would give off radiation that is harmful to our health [13]. A
recent report described the preparation of 2,5,6-substitued
pyrimidines via MgI2-mediated MBH reaction [14]. In this
report, it involves complex catalysts and some toxic solvents
as reaction medium. What’s more, the synthetic procedure
was multistep and some air-sensitive reactions must be
carried out under an atmosphere of argon. Nagarajan and
© 2012 HeteroCorporation

May 2012 An Efficient Synthesis of 4-Naphthylpyrimidin-2-amineDerivatives under Solvent-Free Conditions
697
Table 1
to be a valuable protocol in medicinal chemistry, drug design,
The results of synthesis of 4-(naphthalen-2-yl)-6-arylpyrimidin-2-amine.
and drug discovery because of their simplicity, efficiency,
and high selectivity. It must be an ideal process for
multicomponent reactions, which can be carried out under
solvent-free conditions. Herein, we report the synthesis of
4-naphthylpyrimidin-2-amine derivatives via a simple,
green, one-pot, three-component reaction under solvent-
free conditions.
Entry
Ar
Products
Yields (%)
1
2
3
4
5
6
7
8
4-CH3C6H4
4-CH3OC6H4
3,4-(CH3O)2C6H3
4-FC6H4
4-BrC6H4
4-ClC6H4
4a
4b
4c
4d
4e
4f
91
81
87
90
86
88
89
83
2,4-Cl2C6H3
3,4-Cl2C6H3
4g
4h
RESULTS AND DISCUSSION
First, we carried out the reaction of aromatic aldehyde 1,
2-acetylnaphthalene, guanidine carbonate 3, and sodium
hydroxide in a mortar (Scheme 1). The mixture was ground
and then heated at 70ꢀC under solvent-free conditions for
about 30 min and the reactions could be completed, and the
corresponding 4-(naphthalen-2-yl)-6-arylpyrimidin-2-amine
derivatives were obtained in excellent yields (Table 1).
sodium hydroxide (2 mmol) was ground in a mortar. Then, the
mixture was transferred to a round bottom flask. The mixture was
heated at ∼70ꢀC over the course of 30 min. After the reaction was
completed, the reaction mixture was poured into water, and then
washed with water thoroughly. The product was filtered, dried,
and recrystallized from 95% ethanol.
4-(Naphthalen-2-yl)-6-p-tolylpyrimidin-2-amine (4a). M.p.
154–156ꢀC; IR (KBr, n, cmÀ1): 3326, 3204, 3051, 1645, 1601,
1567, 1536, 1509, 1457, 1363, 1222, 1298, 1185, 1114, 862,
To explore the scope of the reaction, we tried the reac-
tion of naphthaldehyde, aromatic ketones, and guanidine
carbonate. The corresponding 4-(naphthalen-1-yl)-6-aryl-
pyrimidin-2-amine derivatives were obtained in good
yields (Scheme 2). The results were summarized in Table
2. The structures of all the products were confirmed by
1
811, 759, 592 cmÀ1; H-NMR (400 MHz, DMSO-d6) (d, ppm):
2.41 (3H, s, CH3), 6.77 (2H, s, NH2), 7.36 (2H, d, J = 8.0 Hz,
ArH), 7.60 (2H, dd, J = 3.2 Hz, J = 6.4 Hz, ArH), 7.87 (1H, s,
ArH), 8.00 (1H, t, J = 3.2 Hz, ArH), 8.06 (2H, t, J = 8.0 Hz,
ArH), 8.18 (2H, d, J = 8.4 Hz, ArH), 8.36 (1H, dd, J = 1.2 Hz,
J = 1.6 Hz, ArH), 8.84 (1H, s, ArH); Anal. Calcd. for
C21H17N3: C, 81.00; H, 5.50; N, 13.49. Found: C, 81.22; H,
5.57; N, 13.40. HRMS m/z calculated for C21H17N3 [M + Na]+:
334.1320, found: 334.1322.
1
spectroscopic data, particularly H NMR and HRMS.
In conclusion, we have developed an efficient and sim-
ple three-component reaction for the synthesis of 4-
naphthylpyrimidin-2-amine derivatives. This method has
the advantages of operational simplicity, high efficiency,
low cost, and mild reaction conditions. Furthermore, the reac-
tion was performed in good yields within short reaction times.
It is notable that we carried out the reaction use the substrate
with high steric effect under solvent-free conditions. Starting
materials are also inexpensive and commercially available.
4-(4-Methoxyphenyl)-6-(naphthalen-2-yl)pyrimidin-2-amine
(4b). M.p. 143–145ꢀC; IR (KBr, n, cmÀ1): 3323, 3196, 3055,
1645, 1605, 1568, 1537, 1510, 1439, 1363, 1298, 1248, 1176,
1031, 815, 752, 669, 581, 561 cmÀ1 1H-NMR (400 MHz,
;
DMSO-d6) (d, ppm): 3.86 (3H, s, OCH3), 6.73 (2H, s, NH2),
7.10 (2H, d, J = 8.8 Hz, ArH), 7.60 (2H, dd, J = 3.2 Hz, J = 6.4
Hz, ArH), 7.84 (1H, s, ArH), 7.98–8.01 (1H, m, ArH), 8.04–8.08
(2H, m, ArH), 8.25 (2H, d, J = 8.8 Hz, ArH), 8.35 (1H, d, J =
8.8 Hz, ArH), 8.83 (1H, s, ArH); Anal. Calcd. for C21H17N3O: C,
77.04; H, 5.23; N, 12.84. Found: C, 77.22; H, 5.19; N, 12.69.
HRMS m/z calculated for C21H17N3O [M + Na]+: 350.1269, found:
350.1276.
EXPERIMENTAL
Melting points were determined on XT-5 microscopic melting-
point apparatus and were uncorrected. IR spectra were recorded
on a FTIR-8101 spectrometer. 1H-NMR spectra were obtained
from solution in DMSO-d6 with Me4Si as internal standard using
a Bruker-400 spectrometer. Microanalyses were carried out using
a Perkin-Elmer 2400 II analyzer. HRMS spectra were obtained
with a Bruker micrOTOF-Q 134 instrument.
4-(3,4-Dimethoxyphenyl)-6-(naphthalen-2-yl)pyrimidin-2-amine
(4c).
1625, 1576, 1541, 1504, 1439, 1412, 1333, 1270, 1236, 1220,
1175, 1123, 1026, 817, 794, 754, 741, 669 cmÀ1 1H-NMR
M.p. 140–141ꢀC; IR (KBr, n, cmÀ1): 3320, 3198, 3011,
;
(400 MHz, DMSO-d6) (d, ppm): 3.88 (3H, s, OCH3), 3.92 (3H, s,
OCH3), 6.73 (2H, s, NH2), 7.17 (1H, d, J = 8.4 Hz, ArH), 7.65
(2H, dd, J = 2.0 Hz, J = 4.0 Hz, ArH), 7.82 (1H, d, J = 2.0 Hz,
ArH), 7.92–7.97 (2H, m, ArH), 8.09–8.13 (2H, m, ArH), 8.33
(2H, dd, J = 1.6 Hz, J = 8.4 Hz, ArH), 8.85 (1H, s, ArH); Anal.
General procedure for the synthesis of 4-naphthylpyrimidin-
2-amine derivatives. A mixture of aromatic aldehydes (or 1-
naphthaldehyde) 1 (2 mmol), 2-acetylnaphthalene (or aromatic
ketones) 2 (2 mmol), guanidine carbonate 3 (3 mmol), and
Scheme 1.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

698
L. Rong, H. Ji, S. Xia, S. Yin, Y. Shi, and S. Tu
Vol 49
Scheme 2.
1
748, 669 cmÀ1; H-NMR (400 MHz, DMSO-d6) (d, ppm): 6.78
(2H, s, NH2), 7.56 (1H, s, ArH), 7.59–7.61 (2H, m, ArH),
7.62–7.64 (2H, m, ArH), 7.81 (1H, d, J = 2.0 Hz, ArH), 7.99 (2H,
t, J = 2.4 Hz, ArH), 8.26 (2H, dd, J = 1.6 Hz, J = 8.8 Hz, ArH),
8.76 (1H, s, ArH); Anal. Calcd. for C20H13Cl2N3: C, 65.59; H,
3.58; N, 11.47. Found: C, 65.68; H, 3.50; N, 11.57. HRMS m/z
calculated for C20H13Cl2N3 [M + Na]+: 388.0384, found: 388.0399.
4-(3,4-Dichlorophenyl)-6-(naphthalen-2-yl)pyrimidin-2-amine
(4h). M.p. 177–179ꢀC; IR (KBr, n, cmÀ1): 3491, 3326, 3190,
3060, 1622, 1591, 1536, 1512, 1478, 1445, 1433, 1395, 1361,
Table 2
The results of synthesis of 4-(naphthalen-1-yl)- 6-arylpyrimidin-2-amine
Entry
R
Products
Yields (%)
1
2
3
4
5
6
H
4-CH3
4-CH3O
2,4-(CH3)2
3-Cl
7a
7b
7c
7d
7e
7f
91
88
90
81
89
86
2,4-Cl2
1329, 1220, 1104, 829, 808, 788, 745, 669, 563 cmÀ1; H-NMR
1
(400 MHz, DMSO-d6) (d, ppm): 6.73 (2H, s, NH2), 7.57 (1H, d,
J = 1.6 Hz, ArH), 7.61 (3H, t, J = 6.0 Hz, ArH), 7.70 (1H, d,
J = 8.4 Hz, ArH), 7.82 (1H, s, ArH), 8.00 (1H, t, J = 2.0 Hz,
ArH), 8.06 (2H, d, J = 8.8 Hz, ArH), 8.26 (1H, dd, J = 1.6 Hz,
J = 8.8 Hz, ArH), 8.76 (1H, s, ArH); Anal. Calcd. for
C20H13Cl2N3: C, 65.59; H, 3.58; N, 11.47. Found: C, 65.72; H,
3.63; N, 11.38. HRMS m/z calculated for C20H13Cl2N3 [M + Na]+:
388.0384, found: 388.0390.
Calcd. for C22H19N3O2: C, 73.93; H, 5.36; N, 11.76. Found: C,
73.82; H, 5.40; N, 11.89. HRMS m/z calculated for C22H19N3O2
[M + Na]+: 380.1375, found: 380.1389.
4-(4-Fluorophenyl)-6-(naphthalen-2-yl)pyrimidin-2-amine
(4d).
1600, 1570, 1540, 1508, 1456, 1372, 1330, 1221, 1158, 1100, 877,
851, 812, 763, 751, 572, 562, 508 cmÀ1 1H-NMR (400 MHz,
M.p. 156–157ꢀC; IR (KBr, n, cmÀ1): 3327, 3208, 1645,
;
4-(Naphthalen-1-yl)-6-phenylpyrimidin-2-amine (7a).
M.
DMSO-d6) (d, ppm): 6.83 (2H, s, NH2), 7.38 (2H, t, J = 8.8 Hz,
ArH), 7.60–7.63 (2H, m, ArH), 7.90 (1H, s, ArH), 8.00 (1H, t, J =
3.2 Hz, ArH), 8.05–8.08 (2H, m, ArH), 8.33–8.38 (3H, m, ArH),
8.85 (1H, s, ArH); Anal. Calcd. for C20H14FN3: C, 76.18; H, 4.47;
N, 13.33. Found: C, 76.30; H, 4.51; N, 13.42. HRMS m/z
calculated for C20H14FN3 [M + Na]+: 338.1069, found: 338.1070.
4-(4-Bromophenyl)-6-(naphthalen-2-yl)pyrimidin-2-amine
p. 95–97ꢀC; IR (KBr, n, cmÀ1): 3417, 3048, 1628, 1588, 1498,
1445, 1394, 1339, 1322, 1283, 1256, 1177, 1064, 1027, 881, 789,
1
774, 731, 712, 692, 668 cmÀ1; H-NMR (400 MHz, DMSO-d6)
(d, ppm): 6.80 (2H, s, NH2), 7.28–7.34 (3H, m, ArH), 7.45 (1H, t,
J = 8.0 Hz, ArH), 7.53 (1H, d, J = 7.6 Hz, ArH), 7.56–7.61 (3H, m,
ArH), 7.67 (2H, d, J = 7.2 Hz, ArH), 7.94 (1H, d, J = 7.6 Hz,
ArH), 8.00 (1H, d, J = 8.0 Hz, ArH), 8.05 (1H, d, J = 8.0 Hz,
ArH); Anal. Calcd. for C20H15N3: C, 80.78; H, 5.08; N, 14.13.
Found: C, 80.61; H, 5.06; N, 14.20. HRMS m/z calculated for
C20H15N3 [M + Na]+: 320.1164, found: 320.1178.
(4e).
M.p. 180–181ꢀC; IR (KBr, n, cmÀ1): 3303, 3187, 3051,
1633, 1592, 1579, 1541, 1491, 1454, 1363, 1340, 1225, 1104,
1
1072, 1012, 856, 845, 806, 780, 748 cmÀ1; H-NMR (400 MHz,
DMSO-d6) (d, ppm): 6.87 (2H, s, NH2), 7.61 (2H, dd, J = 3.6 Hz,
J = 3.2 Hz, ArH), 7.76 (2H, d, J = 8.8 Hz, ArH), 7.92 (1H, s,
ArH), 8.00 (1H, t, J = 3.2 Hz, ArH), 8.05–8.08 (2H, m, ArH),
8.24 (2H, d, J = 8.4 Hz, ArH), 8.36 (1H, d, J = 8.8 Hz, ArH),
8.85 (1H, s, ArH); Anal. Calcd. for C20H14BrN3: C, 63.84; H,
3.75; N, 11.17. Found: C, 63.67; H, 3.81; N, 11.12. HRMS m/z
calculated for C20H14BrN3 [M + Na]+: 398.0269, found: 398.0272.
4-(4-Chlorophenyl)-6-(naphthalen-2-yl)pyrimidin-2-amine
4-(Naphthalen-1-yl)-6-p-tolylpyrimidin-2-amine (7b). M.p.
141–142ꢀC; IR (KBr, n, cmÀ1): 3322, 3170, 3043, 1649, 1613,
1561, 1535, 1458, 1397, 1351, 1234, 1213, 1185, 1115, 1032, 1018,
820, 797, 776, 752, 643, 594, 572 cmÀ1 1H-NMR (400 MHz,
;
DMSO-d6) (d, ppm): 2.37 (3H, s, CH3), 6.83 (2H, s, NH2), 7.32 (3H,
t, J = 8.0 Hz, ArH), 7.54–7.57 (2H, m, ArH), 7.62 (1H, t, J = 8.0 Hz,
ArH), 7.72 (1H, d, J = 7.2 Hz, ArH), 8.01–8.09 (4H, m, ArH), 8.24
(1H, d, J = 7.2 Hz, ArH); Anal. Calcd. for C21H17N3: C, 81.00; H,
5.50; N, 13.49. Found: C, 81.22; H, 5.11; N, 13.31. HRMS m/z
calculated for C21H17N3 [M + Na]+: 334.1320, found: 334.1333.
4-(4-Methoxyphenyl)-6-(naphthalen-1-yl)pyrimidin-2-amine
(7c). M.p. 152–154ꢀC; IR (KBr, n, cmÀ1): 3481, 3299, 3044,
3001, 2936, 2836, 1638, 1566, 1540, 1514, 1439, 1354, 1303,
(4f).
M.p. 165–167ꢀC; IR (KBr, n, cmÀ1): 3485, 3302, 3186,
1634, 1581, 1568, 1510, 1494, 1457, 1362, 1340, 1225, 1200,
1
1093, 1015, 883, 856, 804, 782, 748 cmÀ1; H-NMR (400 MHz,
DMSO-d6) (d, ppm): 6.87 (2H, s, NH2), 7.60–7.64 (4H, m, ArH),
7.92 (1H, s, ArH), 8.00 (1H, dd, J = 2.4 Hz, J = 3.6 Hz, ArH),
8.05–8.08 (2H, m, ArH), 8.31 (2H, d, J = 8.4 Hz, ArH), 8.36 (1H,
d, J = 8.4 Hz, ArH), 8.85 (1H, s, ArH); Anal. Calcd. for
C20H14ClN3: C, 72.40; H, 4.25; N, 12.66. Found: C, 72.60; H,
4.19; N 12.71. HRMS m/z calculated for C20H14ClN3 [M + Na]+:
354.0774, found: 354.0778.
1253, 1234, 1175, 1029, 822, 807, 781, 649, 581, 525 cmÀ1
;
1H-NMR (400 MHz, DMSO-d6) (d, ppm): 3.83 (3H, s, OCH3),
6.78 (2H, s, NH2), 7.06 (2H, d, J = 8.8 Hz, ArH), 7.32 (1H, s,
ArH), 7.54–7.64 (3H, m, ArH), 7.71 (1H, d, J = 6.8 Hz, ArH),
8.03 (2H, t, J = 8.4 Hz, ArH), 8.13 (2H, d, J = 8.8 Hz, ArH), 8.23
(1H, d, J = 8.0 Hz, ArH); Anal. Calcd. for C21H17N3O: C, 77.04;
H, 5.23; N, 12.84. Found: C, 77.23; H, 5.19; N, 12.76. HRMS m/z
calculated for C21H17N3O [M + Na]+: 350.1269, found: 350.1277.
4-(2,4-Dichlorophenyl)-6-(naphthalen-2-yl)pyrimidin-2-amine
(4g).
3056, 1624, 1591, 1539, 1508, 1474, 1272, 1219, 1103, 860, 815,
M.p. 148–150ꢀC; IR (KBr, n, cmÀ1): 3491, 3323, 3189,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

May 2012 An Efficient Synthesis of 4-Naphthylpyrimidin-2-amineDerivatives under Solvent-Free Conditions
699
REFERENCES AND NOTES
4-(2,4-Dimethylphenyl)-6-(naphthalen-1-yl)pyrimidin-2-amine
(7d). M.p. 145–147ꢀC; IR (KBr, n, cmÀ1): 3399, 3045, 3010,
2949, 1681, 1583, 1446, 1395, 1376, 1320, 1253, 1234, 1167,
[1] Sayle, K. L.; Bentley, J. F.; Boyle, T.; Calvert, A. H.; Cheng, Y.;
Curtin, N. J.; Endicott, J. A.; Golding, B. T.; Hardcastle, I. R.; Jewsbury, P.
Bioorg Med Chem Lett 2003, 13, 3079.
1
1052, 1033, 776 cmÀ1; H-NMR (400 MHz, DMSO-d6) (d, ppm):
2.21 (3H, s, CH3), 2.27 (3H, s, CH3), 6.73 (2H, s, NH2), 7.10–7.13
(1H, m, ArH), 7.44–7.47 (1H, m, ArH), 7.56–7.63 (5H, m, ArH),
7.97 (2H, d, J = 8.0 Hz, ArH), 8.03 (2H, d, J = 8.0 Hz, ArH); Anal.
Calcd. for C22H19N3: C, 81.20; H, 5.89; N, 12.91. Found: C, 81.38;
H, 5.83; N, 12.76. HRMS m/z calculated for C22H19N3 [M + Na]+:
348.1477, found: 348.1498.
[2] Arvanitis, A. G.; Gilligan, P. J.; Chorvat, R. J.; Cheeseman, R. S.;
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5739.
4-(3-Chlorophenyl)-6-(naphthalen-1-yl)pyrimidin-2-amine
(7e).
M.p. 104–106ꢀC; IR (KBr, n, cmÀ1): 3298, 3155, 3047,
1685, 1563, 1537, 1478, 1441, 1396, 1351, 1235, 1213, 1077,
1
878, 777, 719, 699, 627 cmÀ1; H-NMR (400 MHz, DMSO-d6)
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(d, ppm): 6.95 (2H, s, NH2), 7.63 (2H, d, J = 7.2 Hz, ArH), 7.69
(1H, d, J = 7.2 Hz, ArH), 7.75 (1H, d, J = 7.2 Hz, ArH), 7.89
(1H, d, J = 8.0 Hz, ArH), 7.93 (1H, d, J = 8.0 Hz, ArH),
8.02–8.05 (1H, m, ArH), 8.07 (1H, s, ArH), 8.15 (1H, d, J = 7.2
Hz, ArH), 8.18 (1H, s, ArH), 8.24–8.29 (2H, m, ArH); Anal.
Calcd. for C20H14ClN3: C, 72.40; H, 4.25; N, 12.66. Found: C,
72.59; H, 4.19; N, 12.58. HRMS m/z calculated for C20H14ClN3
[M + Na]+: 354.0774, found: 354.0790.
[8] Baskaran, S.; Hanan, E.; Byun, D.; Shen, W. Tetrahedron Lett
2004, 45, 2107.
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Chem 2010, 45, 1583.
4-(2,4-Dichlorophenyl)-6-(naphthalen-1-yl)pyrimidin-2-amine
(7f). M.p. 166–168ꢀC; IR (KBr, n, cmÀ1): 3495, 3423, 3313,
3190, 1627, 1591, 1570, 1535, 1479, 1450, 1399, 1352, 1250,
1211, 1104, 862, 828, 799, 775 cmÀ1 1H-NMR (400 MHz,
;
DMSO-d6) (d, ppm): 7.00 (2H, s, NH2), 7.06 (1H, s, ArH),
7.57–7.64 (4H, m, ArH), 7.70–7.74 (2H, m, ArH), 7.78 (1H, d, J =
1.6 Hz, ArH), 8.04 (2H, dd, J = 5.2 Hz, J = 8.0 Hz, ArH), 8.28
(1H, t, J = 5.2 Hz, ArH); Anal. Calcd. for C20H13Cl2N3: C, 65.59;
H, 3.58; N, 11.47. Found: C, 65.67; H, 4.03; N, 11.51. HRMS m/z
calculated for C20H13Cl2N3 [M + Na]+: 388.0384, found: 388.0397.
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2008, 73, 2621.
Acknowledgements. The authors thank the Natural Science
Foundation of Jiangsu Education Department (No. 08KJB150017) and
the Qing Lan Project (No. 08QLT001) for financial support.
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[20] Shi, D. Q.; Dou, G. L. Synth Commun 2008, 38, 3329.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet