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Taslimahemad T. Khatri and Viresh H. Shah
160.8 (CO−N), 155.4 (C=N), 150.8 (=C−N=), 133.2 (C−N),
132.8 (2CH), 130.4 (2CH), 129.4 (C), 128.0 (CH), 126.7
(2CH), 118.4 (2CH), 115.8 (C−CN), 115.0 (CN), 105.2
(C−CONH), 56.7 (OCH3).
7.12−7.14 (d, 2CH). 13C NMR (DMSO-d6, 100 MHz): δ
178.6 (C−ArCl), 174.2 (CO−NH), 162.8 (CO−N), 158.2
(C=N), 151.4 (=C−N=), 146.2 (C−Cl), 135.2 (CH), 134.8
(CH), 133.2 (C−N), 131.8 (C), 130.4 (CH), 129.2 (2CH),
129.0 (CH), 128.4 (2CH), 126.6 (CH), 115.1 (C−CN), 114.7
(CN), 103.4 (C−CONH).
5-(4-chlorophenyl)-4,7-dioxo-8-phenyl-3,4,7,8-tetrahydro-
pyrido[2,3-d]pyrimidine-6-carbonitrile (10b)
White crystalline solid, IR (KBr): υmax 3198 (NH), 2363
(CN), 1672 (CO), 1588 (C=C), 1556 (C=N), 1144 (C−N),
752 cm−1. MS: m/z 374, 359, 339, 331, 313, 305, 297, 269,
258, 228, 210, 196, 186, 143, 127, 111, 77. Anal. Calcd.
for C20H11ClN4O2: C, 64.09; H, 2.96 N, 14.95%. Found:
C, 63.92; H, 2.85; N, 14.84%. 1H NMR (DMSO-d6, 400
5-(4-bromophenyl)-4,7-dioxo-8-phenyl-3,4,7,8-tetra-
hydropyrido[2,3-d]pyrimidine-6-carbonitrile (10e)
White crystalline solid, IR (KBr): υmax 3189 (NH), 2311
(CN), 1743 (CO−NH), 1689 (CO−N), 1579 (C=C), 1556
(C=N), 1230 (C−N), 1120, 821 cm−1. MS: m/z 418, 375, 347,
339, 263, 186, 154, 77. Anal. Calcd. for C20H11ClN4O2:
Calculated: C, 64.09; H, 2.96 N, 14.95%. Found: C, 63.99;
H, 2.88; N, 14.90%. 1H NMR (DMSO-d6, 400 MHz): δ 11.80
(s, −NHpyrimidine,1H), 8.23 (s, =CHpyrimidine, 1H), 7.99−8.02
(d, J = 11.6 Hz, 2CH), 7.87−7.88 (d, J = 10.4 Hz, 2CH),
7.51−7.53 (d, J = 8.4 Hz, 2CH), 7.40−7.47 (m, 3CH). 13C
NMR (DMSO-d6, 100 MHz): δ 178.4 (C−ArBr), 172.0 (CO−
NH), 164.5 (CO−N), 152.1 (C=N), 149.0 (=C−N=), 147.4
(C−Br), 133.8 (2CH), 131.6 (C−N), 130.4 (C), 129.7 (2CH),
128.8 (CH), 126.4 (2CH), 122.3 (2CH), 117.2 (C−CN),
116.0 (CN), 104.8 (C−CONH).
MHz): δ 11.19 (s, −NHpyrimidine,1H), 7.99 (s, =CHpyrimidine
,
1H), 7.80−7.83 (d, J = 8.4 Hz, 2CH), 7.54−7.63 (m, 3CH),
7.50−7.53 (m, 2CH), 7.37−7.39 (m, 2CH). 13C NMR (DMSO-
d6, 100 MHz): δ 174.4 (C−ArCl), 170.0 (CO−NH), 166.6
(CO−N), 155.8 (C=N), 153.4 (=C−N=), 144.2 (C−Cl), 134.0
(2CH), 132.7 (C−N), 131.5 (C), 130.3 (2CH), 129.4 (CH),
127.4 (2CH), 126.8 (2CH), 115.0 (C−CN), 114.6 (CN),
106.8 (C−CONH).
5-(3-chlorophenyl)-4,7-dioxo-8-phenyl-3,4,7,8-tetrahydro-
pyrido[2,3-d]pyrimidine-6-carbonitrile (10c)
White crystalline solid, IR (KBr): υmax 3218 (NH), 2213
(CN), 1689 (CO−NH), 1682 (CO−N), 1508 (C=C), 1500 (C=N),
1201 (C−N), 788 cm−1. MS: m/z 374, 359, 339, 331, 305,258,
210, 196, 186, 143, 111, 77. Anal. Calcd. for C20H11ClN4O2:
C, 64.09; H, 2.96 N, 14.95%. Found: C, 63.89; H, 2.90; N,
5-(4-nitrophenyl)-4,7-dioxo-8-phenyl-3,4,7,8-tetrahy-
dropyrido[2,3-d]pyrimidine-6-carbonitrile (10f)
Yellow crystalline solid, IR (KBr): υmax 3247 (NH), 2924
(C=C), 2362 (CN), 1694 (CO), 1511 (C=N), 1104 cm−1.
MS: m/z 385, 370, 342, 316, 308, 295, 266, 239, 143, 122,
77. Anal. Calcd. for C20H11N5O4: Calculated: C, 62.34; H,
2.88; N, 18.17%. Found: C, 62.24; H, 2.79; N, 18.06%.
1H NMR (DMSO-d6, 400 MHz): δ11.38 (s, −NHpyrimidine,1H),
7.78 (s, =CHpyrimidine, 1H), 7.60−7.62 (m, 2CH), 7.54−7.60
(m, CH), 7.50−7.53 (dd, J = 7.6 Hz, 2CH), 7.38−7.40 (dd,
J = 7.6 Hz, 2CH). 13C NMR (DMSO-d6, 100 MHz): δ 176.4
(C−ArNO2), 170.2 (CO−NH), 163.8 (CO−N), 150.6 (C=N),
149.2 (=C−N=), 148.4 (C−NO2), 134.0 (2CH), 132.6 (C−N),
131.4 (2CH), 130.8 (2CH), 128.9 (C), 128.3 (CH), 122.8
(2CH), 116.0 (C−CN), 115.7 (CN), 106.5 (C−CONH).
1
14.87%. H NMR (DMSO-d6, 400 MHz): δ 11.56 (s,
−NHpyrimidine,1H), 8.02 (s, =CHpyrimidine, 1H), 7.54−7.55 (d,
J = 8.0 Hz, 2CH), 7.43−7.46 (m, 3CH), 7.37−7.39 (d, J =
8.0 Hz, 2CH), 7.34 (s, CH), 7.30−7.32 (t, J= 7.6 Hz, CH). 13C
NMR (DMSO-d6, 100 MHz): δ 175.8 (C−ArCl), 173.3
(CO−NH), 164.5 (CO−N), 156.8 (C=N), 153.0 (=C−N=),
145.4 (C−Cl), 134.4 (CH), 133.0 (C−N), 132.8 (CH), 132.4
(CH), 130.7 (C), 129.6 (2CH), 128.8 (CH), 127.0 (CH), 126.2
(2CH), 116.4 (C−CN), 115.8 (CN), 105.5 (C−CONH).
5-(2-chlorophenyl)-4,7-dioxo-8-phenyl-3,4,7,8-tetra-
hydropyrido[2,3-d]pyrimidine-6-carbonitrile (10d)
White crystalline solid, IR (KBr): υmax 3233 (NH), 2323
(CN), 1652 (CO−NH), 1603 (CO−N), 1587 (C=C), 1511
(C=N), 734 cm−1. MS: m/z 374, 359, 339, 331, 313, 269,
258, 186, 143, 111, 77. Anal. Calcd. for C20H11ClN4O2: C,
64.09; H, 2.96 N, 14.95%. Found: C, 63.99; H, 2.88; N,
5-(3-nitrophenyl)-4,7-dioxo-8-phenyl-3,4,7,8-tetrahy-
dropyrido[2,3-d]pyrimidine-6-carbonitrile (10g)
Yellow crystalline solid, IR (KBr): υmax 3221 (NH), 2952
(C=C), 2212 (CN), 1714 (CO−NH), 1651 (CO−NH), 1581
(C=C), 1104, 788 cm−1. MS: m/z 385, 370, 342, 316, 295,
239, 122, 77. Anal. Calcd. for C20H11N5O4: C, 62.34; H, 2.88;
N, 18.17%. Found: C, 62.27; H, 2.74; N, 18.00%. 1H NMR
(DMSO-d6, 400 MHz): δ 11.78 (s, −NHpyrimidine,1H), 7.88
(s, =CHpyrimidine, 1H), 7.79−7.81 (d, 2CH), 7.56−7.58 (t, CH),
1
14.90%. H NMR (DMSO-d6, 400 MHz): δ 12.06 (s,
−NHpyrimidine,1H), 7.88 (s, =CHpyrimidine, 1H), 7.71−7.73 (d,
J = 11.6 Hz, 2CH), 7.57−7.61 (m, 3CH), 7.44−7.45 (t, 2CH),
Journal of the Korean Chemical Society