A. Rashidi, M. M. Baradarani, and J. A. Joule
Vol 000
was removed in vacuo, the residue was triturated with water,
collected by filtration, and dried.
6-(3,3-Dimethyl-3H-indol-2-yl)pyrido[2,3-d]pyrimidine-2,4
162.45, 182.87; MS (EI, 70eV): m/z (%) 378 (12), 376 (56),
374 (M+, 100), 359 (35), 347 (13), 332 (22), 320 (12), 289
(9), 226 (13), 212 (17), 198 (10), 173 (12), 136 (13), 115
(36), 99 (10). Found: [M]+ 374.0338, C17H12Cl2N4O2 requires
[M]+ 374.0337.
(1H,3H)-dione (11a).
(0.111 g, Yield 79%); mp 209–212°C;
FT-IR (KBr) νmax/cmÀ1: 3168, 3062, 2852, 1692, 1613,
1520, 1449, 1352, 784; 1H-NMR (DMSO-d6): δ 1.53 (s,
6H), 7.29–7.38 (m, 2H), 7.54 (d, J = 7.2 Hz, 1H), 7.63 (d,
J = 7.2 Hz, 1H), 8.84 (s, 1H), 9.32 (s, 1H), 11.63 (s, 1H),
12.01 (s, 1H); 13C-NMR (DMSO-d6): δ 24.25, 53.45, 110.42,
120.95, 121.95, 123.97, 126.65, 128.27, 135.42, 147.90,
150.78, 152.80, 153.70, 154.18, 162.58, 179.91; MS (EI,
70 eV): m/z (%) 306 (M+, 100), 291 (71), 264 (4), 248 (5), 219
(7), 205 (12), 192 (16), 179 (6), 144 (31), 117 (55), 103 (39),
91 (21), 77 (28), 51 (9). Found: [M]+ 306.1117, C17H14N4O2
requires [M]+ 306.1117.
6-(3,3-Dimethyl-3H-indol-2-yl)-1-methylpyrido[2,3-d]pyrimidine-
2,4(1H,3H)-dione (11f).
(0.106 g, Yield 72%); mp 229–231°C;
FT-IR (KBr) νmax/cmÀ1: 3173, 3055, 2972, 2840, 1709, 1688,
1603, 1487, 762; 1H-NMR (DMSO-d6): δ 1.53 (s, 6H), 3.52
(s, 3H), 7.28–7.34 (m, 2H), 7.53 (d, J = 7.2 Hz, 1H), 7.62 (d,
J = 7.2 Hz, 1H), 8.92 (s, 1H), 9.38 (s, 1H), 11.89 (s, 1H);
13C-NMR (DMSO-d6): δ 24.17, 28.93, 53.46, 111.80, 121,
121.97, 123.76, 126.72, 128.28, 135.79, 147.93. 150.99,
152.76, 153.26, 153.31, 161.48, 179.80; MS (EI, 70 eV): m/z
(%) 320 (M+, 100), 305 (46), 264 (4), 218 (9), 205 (18),
192 (21), 164 (11), 144 (27), 128 (10), 115 (82), 103 (88),
91 (55), 77 (91), 63 (25), 51 (35). Found: [M]+ 320.1273,
C18H16N4O2 requires [M]+ 320.1273.
6-(7-Chloro-3,3-dimethyl-3H-indol-2-yl)pyrido[2,3-d]pyrimidine-
2,4(1H,3H)-dione (11b). (0.116 g, Yield 74%); mp 232–233°C;
FT-IR (KBr) νmax/cmÀ1: 3173, 3062, 2825, 1694, 1615, 1527,
1457, 1368, 790; 1H-NMR (DMSO-d6): δ 1.56 (s, 6H), 7.30
(t, J = 7.8 Hz, 1H), 7.42 (d, J = 7.8 Hz, 1H), 7.53 (d,
J = 7.8 Hz, 1H), 8.89 (d, J = 2.1 Hz, 1H), 9.31 (d, J = 2.1 Hz,
1H), 11.66 (s, 1H), 12.06 (s, 1H); 13C-NMR (DMSO-d6): δ
24.07, 55.05, 110.62, 120.91, 123.64, 125.02, 128.16,
128.51, 135.94, 149.26, 150.11, 150.76, 153.99, 154.21,
162.55, 181.30; MS (EI, 70 eV): m/z (%) 342 (34), 340 (M+,
100), 325 (35), 306 (6), 264 (4), 239 (4), 192 (8), 178 (16),
164 (10), 115 (28), 102 (10), 75 (7). Found: [M]+ 340.0726,
C17H13ClN4O2 requires [M]+ 340.0727.
6-(7-Chloro-3,3-dimethyl-3H-indol-2-yl)-1-methylpyrido[2,3-
d]pyrimidine-2,4(1H,3H)-dione (11g).
(0.120 g, Yield 74%);
mp 242–244°C; FT-IR (KBr) νmax/cm–1: 3174, 3054, 2848,
1719, 1691, 1610, 1502, 1334, 753; 1H-NMR (DMSO-d6): δ
1.57 (s, 6H), 3.54 (s, 3H), 7.31 (t, J = 7.8 Hz, 1H), 7.41 (d,
J = 7.8 Hz, 1H), 7.52 (d, J = 7.8 Hz, 1H), 8.99 (s, 1H), 9.4 (s,
1H), 11.92 (s, 1H); 13C-NMR (DMSO-d6): δ 24, 28.97, 55.06,
112, 120.93, 123.44, 125.07, 128.33, 128.52, 136.29, 149.23,
150.15, 150.99, 153.37, 153.53, 161.47, 181.19; MS (EI,
70 eV): m/z (%) 356 (33), 354 (M+, 100), 339 (31), 319 (4), 239
(8), 205 (10), 192 (12), 178 (35), 164 (19), 137 (14), 115 (92),
102 (35), 89 (27), 75 (30). Found: [M]+ 354.0885,
C18H15ClN4O2 requires [M]+ 354.0884.
6-(3,3,7-Trimethyl-3H-indol-2-yl)pyrido[2,3-d]pyrimidine-2,4
(1H,3H)-dione (11c).
(0.112g, Yield 76%); mp 221–224°C;
FT-IR (KBr) νmax/cmÀ1: 3165, 3023, 2851, 1709, 1613, 1516,
1445, 1359, 1270, 757; 1H-NMR (DMSO-d6): δ 1.52 (s, 6H),
2.56 (s, 3H), 7.16–7.18 (m, 2H), 7.32 (d, J = 7.5 Hz, 1H), 8.86
(s, 1H), 9.30 (s, 1H), 11.62 (s, 1H), 11.97 (s, 1H); 13C-NMR
(DMSO-d6): δ 16.96, 24.32, 53.64, 110.47, 119.26, 124.25,
126.65, 129.31, 130.28, 135.46, 147.76, 150.76, 151.29,
153.59, 154.01, 162.63, 178.66; MS (EI, 70eV): m/z (%) 320
(M+, 100), 305 (25), 264 (5), 229 (27), 219 (5), 201 (60), 186
(75), 168 (10), 158 (42), 143 (14), 125 (14), 115 (34), 97
(35), 83 (31), 69 (33), 57 (39). Found: [M]+ 320.1273,
C18H16N4O2 requires [M]+ 320.1273.
1-Methyl-6-(3,3,7-trimethyl-3H-indol-2-yl)pyrido[2,3-d]
pyrimidine-2,4(1H,3H)-dione (11h). (0.118g, Yield 77%); mp
233–234°C; FT-IR (KBr) νmax/cmÀ1: 3170, 3043, 2924, 2855,
1695, 1611, 1505, 1462, 758; 1H-NMR (DMSO-d6): δ 1.52
(s, 6H), 2.54 (s, 3H), 3.53 (s, 3H), 7.16–7.18 (m, 2H), 7.32
(d, J = 7.5 Hz, 1H), 8.95 (s, 1H), 9.38 (s, 1H), 11.90 (s,
1H); 13C-NMR (DMSO-d6): δ 16.93, 24.25, 28.91, 53.65,
111.83, 119.27, 124.04, 126.72, 129.31, 130.33, 135.83,
147.80, 150.97, 151.26, 153.13, 153.19, 161.52, 178.54; MS
(EI, 70 eV): m/z (%) 334 (M+, 100), 319 (59), 278 (8), 235
(10), 219 (14), 158 (18), 144 (12), 115 (31), 91 (27), 77
(8). Found: [M]+ 334.1429, C19H18N4O2 requires [M]+
334.1429.
6-(5-Methoxy-3,3-dimethyl-3H-indol-2-yl)pyrido[2,3-d]
pyrimidine-2,4(1H,3H)-dione (11d). (0.104g, Yield 67%); mp
236–237°C; FT-IR (KBr) νmax/cmÀ1: 3169, 3059, 2837, 1700,
1613, 1525, 1461, 1369, 1281, 794; 1H-NMR (DMSO-d6): δ 1.52
(s, 6H), 3.77 (s, 3H), 6.89 (d, J = 8.4 Hz, 1H), 7.17 (s, 1H), 7.53
(d, J = 8.4 Hz, 1H), 8.78 (s, 1H), 9.27 (s, 1H), 11.62 (s, 1H), 11.99
(s, 1H); 13C-NMR (DMSO-d6): δ 24.36, 53.61, 56.03, 108.15,
110.33, 113.56, 121.51, 124.26, 134.91, 146.40, 149.75, 150.77,
153.38, 153.86, 158.95, 162.62, 177.71; MS (EI, 70 eV): m/z (%)
336 (M+, 100), 321 (81), 305 (8), 293 (29), 278 (12), 264 (3), 235
(7), 207 (9), 174 (9), 147 (8), 117 (10), 103 (11), 90 (8), 77 (13),
63 (6). Found: [M]+ 336.1222, C18H16N4O3 requires [M]+
336.1222.
6-(5-Methoxy-3,3-dimethyl-3H-indol-2-yl)-1-methylpyrido[2,3-
d]pyrimidine-2,4(1H,3H)-dione (11i).
(0.128 g, Yield 79%);
mp 249–252°C; FT-IR (KBr) νmax/cmÀ1: 3186, 3067, 2968,
1710, 1681, 1604, 1480, 1283, 826; 1H-NMR (DMSO-d6): δ
1.52 (s, 6H), δ 3.51 (s, 3H), δ 3.78 (s, 3H), 6.89 (d,
J = 8.4 Hz, 1H), 7.16 (s, 1H), 7.52 (d, J = 8.4Hz, 1H), 8.87 (s,
1H), 9.34 (s, 1H), 11.87 (s, 1H); 13C-NMR (DMSO-d6): δ
24.29, 28.90, 53.61, 56.02, 108.18, 111.73, 113.51, 121.56,
124.03, 135.30, 146.37, 149.80, 150.99, 152.92, 152.98,
158.97, 161.52, 177.56; MS (EI, 70 eV): m/z (%) 350 (M+,
100), 335 (60), 307 (24), 292 (9), 221 (5), 174 (9), 126 (8),
103 (11), 77 (12). Found: [M]+ 350.1379, C19H18N4O3 requires
[M]+ 350.1379.
6-(4,6-Dichloro-3,3-dimethyl-3H-indol-2-yl)pyrido[2,3-d]
pyrimidine-2,4(1H,3H)-dione (11e). (0.142 g, Yield 82%);
mp 254–256°C; FT-IR (KBr)
ν
max/cmÀ1
:
3177, 3075,
1
2800,1692, 1604, 1516, 1436, 1370, 854; H-NMR (DMSO-d6):
δ 1.67 (s, 6H), 7.45 (d, J = 1.5 Hz, 1H), 7.73 (d, J = 1.5 Hz, 1H),
8.85 (s, 1H), 9.31 (s, 1H), 11.67 (s, 1H), 12.09 (s, 1H); 13C-NMR
(DMSO-d6): δ 20.61, 55.55, 110.56, 120.46, 122.86, 126.53,
129.09, 133.83, 136.16, 141.58, 150.77, 154.18, 154.51, 155.71,
6-(3,3-Dimethyl-3H-indol-2-yl)-1,3-dimethylpyrido[2,3-d]
pyrimidine-2,4(1H,3H)-dione (11j). (0.107 g, Yield 70%);
mp 237–241°C; FT-IR (KBr) νmax/cmÀ1: 3053, 2978, 1667, 1611,
1503, 1335, 1290, 778; 1H-NMR (DMSO-d6): δ 1.54 (s, 6H),
3.31 (s, 3H), 3.60 (s, 3H), 7.28–7.35 (m, 2H), 7.54 (d, J = 7.2 Hz,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet