A Green Synthesis of 7-amino-5-(4-aroyl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine-6-carbonitrile Derivatives by a One-pot Three-component Reaction

Article abstract of DOI:10.1002/jhet.2930

The synthesis of polyfunctionalized 7-amino-5-(4-aroyl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine-6-carbonitrile derivatives by a green approach was achieved via one-pot three-component reaction of arylglyoxals, malononitrile, and 1,3-dimethyl-6-aminouracil in the presence of urea as organocatalyst in EtOH:H₂O (1:1) at 60°C. This protocol provides a mild and fast procedure to structurally diverse bicyclic pyridopyrimidines in good to excellent yields.

Full text of DOI:10.1002/jhet.2930

Month 2017
A Green Synthesis of 7-amino-5-(4-aroyl)-1,3-dimethyl-2,4-dioxo-
1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine-6-carbonitrile Derivatives
by a One-pot Three-component Reaction
*
and Jabbar Khalafy
Ramin Javahershenas
Department of Chemistry, Urmia University, 5756151818 Urmia, Iran
*
E-mail: jkhalafi@yahoo.com; j.khalafi@urmia.ac.ir
Received March 16, 2017
DOI 10.1002/jhet.2930
Published online 00 Month 2017 in Wiley Online Library (wileyonlinelibrary.com).
The synthesis of polyfunctionalized 7-amino-5-(4-aroyl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,5,8-
hexahydropyrido[2,3-d]pyrimidine-6-carbonitrile derivatives by a green approach was achieved via one-
pot three-component reaction of arylglyoxals, malononitrile, and 1,3-dimethyl-6-aminouracil in the presence
of urea as organocatalyst in EtOH:H2O (1:1) at 60°C. This protocol provides a mild and fast procedure to
structurally diverse bicyclic pyridopyrimidines in good to excellent yields.
J. Heterocyclic Chem., 00, 00 (2017).
INTRODUCTION
corresponding arylglyoxals as their hydrates (2a–i)
(Scheme 1).
Multicomponent reactions (MCRs) play an important
role in the synthesis of heterocyclic compounds by
forming more than one carbon–carbon or carbon–
heteroatom bonds in organic synthesis through
environmentally and economically useful one-pot
procedures [1].
Recently, the pyrido[2,3-d]pyrimidine derivatives
have received considerable attention because of their
biological [2,3] and pharmacological [4–6] activities such
as anti-AIDS [7], antifungal [8], antileishmanial [9],
tuberculostatic [10], antimicrobial [11], antitumor [12],
tyrosin ekinase [13], anti-inflammatory [14], antiallergic
[15], analgesic [16], antibronchitic [17], hepatoprotective
[18], antihypertensive [19], calcium channel antagonists
[20], and antibacterial [21].
Reaction of 1,3-dimethyl-6-aminouracil 3, arylglyoxal
(2a–i) and malononitrile 4 in the presence of urea as
organocatalyst in EtOH:H2O at 60°C gave the desired
polyfunctionalized 7-amino-5-(4-aroyl)-1,3-dimethyl-2,4-
dioxo-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine-6-
carbonitrile derivatives (5a–i) as shown in Scheme 2.
In our initial studies, the reaction of phenylglyoxal (2a),
1,3-dimethyl-6-aminouracil (3), and malononitrile (4) was
chosen as a model reaction (Table 1). First, we carried
out this model reaction in the absence of catalyst, but no
product was observed even after 24 h of stirring at room
temperature (Table 1, entry 7). Refluxing the reaction
mixture in EtOH:H2O (1:1) without any catalyst for 24 h
gave the desired product 5a in only 18% yield (Table 1,
entry 9). The use of 5 and 10 mol% of urea as
organocatalyst for this reaction improved the yield
(Table 2, entries 7–8), but using 15 mol% of urea and
refluxing the reaction mixture for 2 h decreased the yield
to 63% (Table 2, entry 9). The product was fully
In continuation of our interests in synthesis of new
heterocyclic compounds by one-pot multicomponent
reactions [22–26], herein, we report the synthesis of
7-amino-5-(4-aroyl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,5,8-
1
hexahydropyrido[2,3-d]pyrimidine-6-carbonitriles by
a
characterized by FTIR, H-NMR, and 13C-NMR spectra.
one-pot three-component reaction of arylglyoxals (2a–i),
1,3-dimethyl-6-aminouracil 3 and malononitrile 4 in the
presence of a catalytic amount of urea in EtOH:H2O(1:1)
at 60°C in high yields.
To optimize the reaction temperature, the reactions were
carried out at different temperatures ranging from room
temperature to reflux. It was found that the yield was
improved and the reaction time was shortened when the
temperature was increased to 60°C. No significant change
in the yield was observed when the temperature was
further increased to reflux (Table 1, entries 10–13).
RESULTS AND DISCUSSION
The best result was obtained in terms of yield (78%) and
reaction time (2 h) when the reaction was performed using
10 mol% of urea (Table 1, entry 12). To find the best
Oxidation of acetophenones 1a–i with selenium dioxide
in EtOH under reflux conditions [27] gave the
© 2017 Wiley Periodicals, Inc.

R. Javahershenas and J. Khalafy
Vol 000
Scheme 1. Preparation of arylglyoxal hydrates (2a–i) by oxidation of acetophenones.
Scheme 2. Synthesies of pyrido[2,3-d]pyrimidine-6-carbonitrile derivatives (5a–i).
Table 1
The effect of several solvents, temp, and mol% of urea on synthesis of 5a.
Entry
Catalyst
Temperature (°C)
Solvent
Time (h)
Yield (%)
1
2
3
4
5
6
7
8
Urea (10 mol %)
Urea (10 mol %)
Urea (10 mol %)
Urea (10 mol %)
Urea (10 mol %)
Urea (10 mol %)
No catalyst
No catalyst
No catalyst
Urea (10 mol %)
Urea (10 mol %)
Urea (10 mol %)
Urea (10 mol %)
60
60
60
60
60
60
RT
60
Reflux
RT
40
THF
EtOH
CH2Cl2
CH3CN
DMF
H2O
EtOH/H2O
EtOH/H2O
EtOH/H2O
EtOH/H2O
EtOH/H2O
EtOH/H2O
EtOH/H2O
2
2
2
2
2
24
58
28
27
55
2
63
24
24
24
2
2
2
Trace
Trace
18
18
61
9
10
11
12
13
60
Reflux
78
66
2
Phenyglyoxal (1 mmol), malononitrile (1 mmol) and 1,3-dimethyl-6-aminouracil (1 mmol) EtOH:H2O (1:1) (5 mL).
Table 2
The effect of several catalysts in the synthesis of 5a.
Entry
Catalyst
Temperature ( C)
Solvent
Time (h)
Yield (%)
1
2
3
4
5
6
7
8
9
—
60
60
60
60
60
60
RT
60
Reflux
RT
THF
EtOH
CH2Cl2
CH3CN
DMF
24
5
5
5
5
5
2
2
2
3
trace
46
51
59
68
71
53
78
59
72
K2CO3 (10 mol %)
p-TSA (10 mol %)
SDS (10 mol %)
TBAB (10 mol %)
L-Proline (10 mol %)
Urea (5 mol %)
Urea (10 mol %)
Urea (15 mol %)
Thiourea (10 mol %)
H2O
EtOH/H2O
EtOH/H2O
EtOH/H2O
EtOH/H2O
10
Phenyglyoxal (1 mmol), malononitrile (1 mmol) and 1,3-dimethyl-6-aminouracil (1 mmol) EtOH:H2O (1:1) (5 mL).
solvent for this reaction, we repeated the model reaction in
various solvents such as acetonitrile (MeCN),
dichloromethane (DCM), tetrahydrofuran (THF), and
water (H2O), the use of EtOH:H2O (1:1) proved to be
best in terms of yield and reaction time (Table 1, entry12).
We examined this reaction in the absence and presence
of several other catalysts. When the reaction was carried
out without any catalysts, only a trace amount of product
was obtained (Table 2, entry 1). Bases or acids such as
K2CO3 or p-toluene sulfonic acid (PTSA) increased the
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2017
A Green Synthesis of pyrido[2,3-d]pyrimidine-6-Carbonitrile Derivatives
reaction yield (Table 2, entries 2 and 3). When surfactants,
such as sodium dodecyl sulfate (SDS), L-Proline, and n-
tetrabutylammonium bromide (TBAB) were used in this
reaction, the yields of the products were improved
(Table 2, entries 4–6). The best result was obtained when
urea was used as a catalyst giving a yield of 78%.
To study the effect of the amount of catalyst, the
reactions were carried out with different amounts of urea
ranging from 5 to 15 mol%. It was found that by
increasing the amount of urea from 5 to 10 mol%, the
yield was increased. Thus, 10 mol% urea in EOH: H2O
(1:1) is sufficient to push this reaction forward. Using the
larger amounts of urea more than 10 mol% did not
improve the yields.
1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine-6-carbonitriles
derivatives (5a–i) are shown in Table 3.
The substituted 7-amino-5-(4-aroyl)-1,3-dimethyl-2,4-
dioxo-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine-6-
carbonitrile derivatives (5a–i) were characterized using
FTIR, 1H-NMR, and 13C-NMR spectroscopy, and
microanalysis. The characteristic singlet at around δ
5.17–5.52 ppm was ascribed to the CH of the
dihydropyridine ring and was present in all new
products. The characteristic singlets at around
3.24–3.35 ppm and δ 3.48–3.52 ppm are attributed to
the 1-methyl and 3-methyl groups of the
δ
dihydropyridine ring, respectively, and were present in
all new products. In the 13C-NMR spectra of the
The reaction times, melting points, and yields of
synthesized 7-amino-5-(4-aroyl-1,3-dimethyl-2,4-dioxo-
products
(5a–p),
signals
located
around
δ
189.08–194.53 ppm were attributed to the carbonyl
Table 3
The yields, melting points, and reaction times of products (5a–i).a
Entry
Product
Ar
Mp (°C)
Time (h)
Yield (%)
1
2
3
4
5
6
7
8
9
5a
5b
5c
5d
5e
5f
5g
5h
5i
C6H5
>300
>300
>300
>300
>300
>300
>300
>300
>300
5
4
6
6
6
5
4
4
5
78
86
71
81
65
85
79
78
73
4-MeC6H4
4-O2NC6H4
4-ClC6H4
4-FC6H4
4-MeOC6H4
4-HOC6H4
3,4-(MeO)2C6H3
4-BrC6H4
aThe yields are referred to the recrystallized products.
Scheme 3. The proposed mechanism for the one-pot three-component reaction.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

R. Javahershenas and J. Khalafy
Vol 000
groups of arylglyoxal moieties. The signals located
around δ 161.10–166.32 and 159.33–160.92 ppm were
due to C-2 and C-4 carbonyl groups, respectively. In
the FTIR spectra, the characteristic absorption bonds at
2226–2256 cmÀ1 could be assigned to the vibrations of
nitrile groups. The absorption bonds at 1690–1726,
1639–1700, and 1603–1653 cmÀ1 could be assigned to
the vibrations of three different carbonyl groups.
EtOAc:hexane (7:3) as eluent. After completion of the
reaction, the precipitate was filtered, washed with cold
EtOH:H2O (1:1), and dried. Recrystallization from EtOH
gave the desired products in 65–88% yields (Table 2).
7-Amino-5-(benzoyl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,5,8-
hexahydropyrido[2,3-d]pyrimidine-6-carbonitrile (5a).
Yield: 78%; white powder; mp > 300°C. FTIR νmax
3393, 3231, 2832, 2347, 1726, 1693, 1652, 1559, 1448,
1303, 1208, 1096, 875,820, 523 cmÀ1 1H-NMR
:
.
Mechanistically, the formation of the product (5a–i) was
(DMSO-d6) δ (ppm): 12.04 (s, 1H, exchanged by D2O
addition, NH), 7.59 (bs, 1H, exchanged by D2O addition,
1H of NH2), 7.56 (bs, 1H, exchanged by D2O addition,
1H of NH2), 7.57 (d, J = 7.8 Hz, 2H, Ar), 7.51
(t, J = 7.5 Hz, 2H, Ar), 7.43 (t, J = 7.2 Hz, 1H,Ar), 5.28
(s, 1H, CH), 3.50 (s, 3H,3-Me), 3.25 (s, 3H,
1-Me).13C-NMR (DMSO-d6) δ (ppm): 193.85, 166.20,
159.34, 150.97, 140.32, 130.20, 129.29, 129.00, 128.75,
117.27, 106.41, 97.81, 35,64, 35.50, 28.02. Anal. Calcd
for C17H15N5O3: C, 60.53 H, 4.48 N, 20.76. Found: C,
achieved by
a
sequence of reactions involving
Knoevenagel condensation of malononitrile with
aryglyoxal by loss of a water molecule, then the Michael
addition of 1,3-dimethyl-6-aminouracil to the product,
followed by intramolecular heterocyclization and
tautomerization.The probable mechanism is shown in
Scheme 3.
CONCLUSIONS
60.68 H, 4.34 N, 20.92%.
7-Amino-5-(4-methylbenzoyl)-1,3-dimethyl-2,4-dioxo-
1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine-6-carbonitrile
We have synthesized a new series of 7-amino-5-(4-aroyl)-
1,3-dimethyl-2,4-dioxo-1,2,3,4,5,8-hexahydropyrido[2,3-d]
pyrimidine-6-carbonitrile derivatives (5a–i) by a one-pot
three-component reaction of 1,3-dimethyl-6-aminouracil 3
with arylglyoxals 2a–i and malononitrile using 10 mol%
urea as catalyst at 60°C in EtOH:H2O (1:1) in high yields.
The advantages of this procedure are simplicity, ease of
product isolation, mild reaction conditions, high yield, and
short reaction times.
(5b).
Yield: 86%; white powder; mp > 300°C. FTIR
ν
max: 3427, 3149, 3055, 2943, 2237, 1676, 1670, 1642,
1559, 1450, 1370, 1277, 1115, 1033, 975, 830, 754,
1
634 cmÀ1. H-NMR (DMSO-d6) δ (ppm): 11.98 (s, 1H,
exchanged by D2O addition, NH), 7.54 (bs, 1H,
exchanged by D2O addition,1H of NH2), 7.50(bs, 1H,
exchanged by D2O addition, 1H of NH2), 7.46 (d,
J = 7.8 Hz, 2H, Ar), 7.31 (d, J = 7.8 Hz, 2H, Ar), 5.27
(s, 1H, CH), 3.49 (s, 3H, 3-Me), 3.24 (s, 3H, 1-Me), 2.36
(s, 3H, Me).13C-NMR (DMSO-d6) δ (ppm): 189.08,
166.16, 159.35, 150.96, 140.06, 138.25, 129.56, 127.33,
127.27, 117.27, 105.95, 97.72, 35.64, 31.14, 28.00,
21.30. Anal. Calcd for C18H17N5O3: C, 61.53 H, 4.88 N,
EXPERIMENTAL
The chemicals used in this work were purchased from
Arcos and Merck companies and were used without
purification. Freshly distilled solvents were used
throughout, and anhydrous solvents were dried according
to Perrin and Armarego [28]. Melting points were
measured on an Electro thermal 9200 apparatus and are
19.93. Found: C, 61.71 H, 4.71 N, 20.15%.
7-Amino-5-(4-nitrobenzoyl)-1,3-dimethyl-2,4-dioxo-
1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine-6-carbonitrile
(5c). Yield: 71%; orange powder; mp > 300°C. FTIR
ν
max: 3432, 3388, 2955, 2256, 1695, 1690, 1639, 1516,
1450, 1339, 1255, 1225, 1110, 976, 858, 755, 701 cmÀ1
.
uncorrected. FTIR spectra were recorded on
a
1H-NMR (DMSO-d6) δ (ppm): 12.24 (s, 1H, exchanged
by D2O addition, NH), 8.34 (d, J = 8.7 Hz, 2H, Ar), 8.28
(bs, 1H, exchanged by D2O addition, 1H of NH2), 8.25
(bs, 1H, exchanged by D2O addition, 1H of NH2), 7.85
(d, J = 8.7 Hz, 2H, Ar), 5.52(s, 1H, CH), 3.51 (s, 3H, 3-
Me), 3.25 (s, 3H, 1-Me). 13C-NMR (DMSO-d6) δ (ppm):
194.53, 165.77, 159.33, 150.92, 140.95, 129.97, 127.78,
124.03, 123.72, 116.99, 109.15, 98.51, 35.39, 31.23, and
28.05. Anal. Calcd for C17H14N6O5: C, 53.41 H, 3.69 N,
Thermonicolet (Nexus 670) spectrometer using KBr
discs. 1H NMR (300 MHz) and 13C NMR (75 MHz)
spectra were recorded on a Bruker DRX-300 Advance
spectrometer in DMSO-d6 with TMS as the internal
reference. Elemental analyses were performed using a
Leco Analyzer 932.
General procedure for synthesis of 7-amino-5-(4-aroyl)-1,3-
dimethyl-2,4-dioxo-1,2,3,4,5,8-hexahydropyrido[2,3-d]
pyrimidine-6-carbonitrile derivatives.
A mixture of
arylglyoxal (1 mmol), malononitrile (1.1 mmol), 1,3-
dimethyl-6-aminouracil (1 mmol), and urea (10 mol %)
in EtOH:H2O (1:1) (5 mL) was stirred at 60°C for the
appropriate time as indicated in Table 3. The reaction was
monitored by thin-layer chromatography (TLC) using
21.98. Found: C, 53.58, H, 3.58 N, 22.28%.
7-Amino-5-(4-chlorobenzoyl)-1,3-dimethyl-2,4-dioxo-
1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine-6-carbonitrile
(5d).
Yield: 81%; white powder; mp > 300°C. FTIR
ν
max: 3406, 3367, 3298, 3159, 2226, 1703, 1690, 1603,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2017
A Green Synthesis of pyrido[2,3-d]pyrimidine-6-Carbonitrile Derivatives
1445, 1401, 1246, 1093, 973, 810, 551 cmÀ1.1H-NMR
(DMSO-d6) δ (ppm): 12.06 (s, 1H, exchanged by D2O
addition, NH), 7.65–7.40 (m, 6H, Ar + NH2), 5.36 (s,
1H, CH), 3.49 (s, 3H, 3-Me), 3.24(s, 3H, 1-Me).13C-
NMR (DMSO-d6) δ (ppm): 189.80, 166.13, 159.36,
150.93, 140.37, 133.47, 131.03, 129.10, 128.94, 117.15,
107.00, 97.87, 35.50, 31.16, 28.02. Anal. Calcd for
C17H14ClN5O3: C, 54.92 H, 3.80 N, 18.84. Found: C,
159.35, 149.36, 148.83, 130.71, 130.29, 122.53, 117.30,
105.55, 97.60, 35.68, 31.14, 28.02. Anal. Calcd for
C17H15N5O4: C, 57.79 H, 4.28 N, 19.82. Found: C, C,
57.92 H, 4.15 N, 19.68%.
7-Amino-5-(3,4-dimethoxybenzoyl)-1,3-dimethyl-2,4-dioxo-
1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine-6-carbonitrile
(5h).
Yield: 78%; white powder; mp > 300°C. FTIR
ν
max: 3379, 3290, 3199, 2960, 2252, 1697, 1685, 1638,
1564, 1517, 1447, 1375, 1273, 1237, 1028, 842,
55.09 H, 3.92 N, 18.71%.
1
647 cmÀ1. H-NMR (DMSO-d6) δ (ppm): 11.95 (s, 1H,
7-Amino-5-(4-fluorobenzoyl)-1,3-dimethyl-2,4-dioxo-
1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine-6-carbonitrile
(5e). Yield: 65%; pale green powder; mp > 300°C. FTIR
exchanged by D2O addition, NH), 7.58 (bs, 2H,
exchanged by D2O addition, NH2), 7.22 (s, 1H, Ar), 7.11
(d, J = 7.8 Hz, 1H, Ar), 7.08 (d, J = 7.8 Hz, 1H, Ar),
5.34 (s, 1H, CH), 3.83 (s, 3H, OMe), 3.80 (s, 3H, OMe),
3.50 (s, 3H, 3-Me), 3.25 (s, 3H, 1-Me).13C-NMR
(DMSO-d6) δ (ppm): 192.80, 166.10, 159.35, 149.39,
148.83, 140.02, 131.89, 131.27, 122.14, 117.31, 114.34,
107.01, 97.91, 57.14, 55.82, 35.67, 31.10, 28.01.
Anal. Calcd for C19H19N5O5: C, 57.43 H, 4.82 N, 17.62.
ν
max: 3427, 3149, 3057, 2944, 2241, 1690, 1678, 1642,
1561, 1484, 1277, 1098, 1021, 975, 844, 742, 628 cmÀ1
.
1H-NMR (DMSO-d6) δ (ppm): 12.05 (s, 1H, exchanged
by D2O addition, NH), 7.62 (t, J = 8.7 Hz, 2H, Ar), 7.58
(bs, 1H, exchanged by D2O addition, 1H of NH2), 7.54
(bs, 1H, exchanged by D2O addition, 1H of NH2), 7.36
(t, J = 8.7 Hz, 2H, Ar), 5.31 (s, 1H, CH), 3.49 (s, 3H, 3-
Me), 3.25 (s, 3H, 1-Me).13C-NMR (DMSO-d6) δ (ppm):
189.80, 166.23, 164.20, 160.92, 159.38, 150.95, 140.23,
131.54, 129.28, 126.72, 116.06, 115.77, 106.69, 97.69,
35.52, 31.13, 28.02. Anal. Calcd for C17H14FN5O3: C,
57.46 H, 3.97 N, 19.71. Found: C, 57.54 H, 3.83 N,
Found: C, 57.58 H, 4.75 N, 17.77%.
7-Amino-5-(4-bromobenzoyl)-1,3-dimethyl-2,4-dioxo-
1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine-6-carbonitrile
(5i). Yield: 73%; pale pink powder; mp > 300°C. FTIR
ν
max: 3459, 3337, 2958, 2888, 2248, 1695, 1639, 1642,
1599, 1556, 1485, 1318, 1276, 1117, 1031, 974, 892,
19.59%.
1
742 cmÀ1. H-NMR (DMSO-d6) δ (ppm): 12.07 (s, 1H,
7-Amino-5-(4-methoxybenzoyl)-1,3-dimethyl-2,4-dioxo-
1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine-6-carbonitrile
(5f). Yield: 85%; white powder; mp > 300°C. FTIR
exchanged by D2O addition, NH), 7.71 (d, J = 8.4 Hz,
2H, Ar), 7.58 (bs, 1H, exchanged by D2O addition, 1H of
NH2), 7.55 (bs, 1H, exchanged by D2O addition, 1H of
NH2), 7.52 (d, J = 8.4 Hz, 2H, Ar), 5.36(s, 1H, CH),
3.49 (s, 3H, 3-Me), 3.24 (s, 3H, 1-Me).13C-NMR
(DMSO-d6) δ (ppm): 189.80, 166.10, 159.35, 150.93,
140.42, 131.89, 131.27, 129.46, 128.98, 122.14, 117.15,
107.01, 97.91, 35.48, 31.16, 28.03. Anal. Calcd for
C17H14BrN5O3: C, 49.06 H, 3.39 N, 16.83. Found: C,
49.17 H, 3.26 N, 16.67%.
ν
max: 3393, 3198, 2951, 2839, 2245, 1692, 1643, 1623,
1559, 1505, 1441, 1377, 1286, 1254, 1180, 1029, 839,
1
639 cmÀ1. H-NMR (DMSO-d6) δ (ppm): 11.95 (s, 1H,
exchanged by D2O addition, NH), 7.57 (bs, 1H,
exchanged by D2O addition, 1H of NH2), 7.53 (bs, 1H,
exchanged by D2O addition,1H of NH2), 7.50 (d,
J = 8.7 Hz, 2H, Ar), 7.07 (d, J = 8.7 Hz, 2H, Ar),
5.23 (s, 1H, CH), 3.81 (s, 3H, OMe), 3.49 (s, 3H, 3-
Me), 3.35 (s, 3H, 1-Me).13C-NMR (DMSO-d6)
δ
(ppm): 193.25, 166.32, 159.81, 159.35, 150.95, 140.02,
130.71, 130.29, 122.53, 117.31, 105.55, 97.59, 55.82,
35.68, 31.14, 28.02. Anal. Calcd for C18H17N5O4: C,
58.85 H, 4.66 N, 19.06. Found: C, 58.94 H, 4.53 N,
Acknowledgments. We are grateful to the University of Urmia
for financial support.
19.18%.
7-Amino-5-(4-hydroxybenzoyl)-1,3-dimethyl-2,4-dioxo-
1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine-6-carbonitrile
REFERENCES AND NOTES
(5g).
Yield: 79%; white powder; mp > 300°C. FTIR
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet