K. Bischoff et al. · 6-Substituted Pyrido[2,3-d]pyrimidine(1H,3H)-2,4-diones
493
[D6]-DMSO): δ = 11.2 (C-3”’), 19.7 (C-2”’), 23.1 (C-1’), J = 7.4 Hz, 2H, 1’-H), 2.95 (t, J = 7.4 Hz, 2H, 2’-H), 3.13
27.6 (N3-CH3), 32.6 (N1-CH3), 37.8 (C-2’), 48.4 (C-1”’), (s, 3H, N3-CH3), 3.38 (s, 3H, N1-CH3), 4.26 (d, J = 7.0 Hz,
94.4 (C-5), 127.8 (C-3”), 128.6 (C-2”), 133.1 (C-4”), 136.5 2H, NH-CH2), 6.11 (t, J = 7.1 Hz, 1H, NH), 7.23 (mc, 1H,
(C-1”), 151.6 (C-6), 153.5 (C-2), 162.5 (C-4), 200.2 (C-3’). 4”’-H), 7.31 (mc, 4H, 2”’-H, 3”’-H), 7.50 (mc, 2H, 3”-H),
– EI-MS: m/z = 329 [M+] (10), 197 (100). – C18H23N3O3 7.62 (mc, 1H, 4”-H), 7.89 (mc, 2H, 2”-H). – 13C NMR
(329.40): calcd. C 65.63, H 7.04, N 12.76; found C 65.83, (75 MHz, [D6]-DMSO): δ = 19.5 (C-1’), 27.6 (N3-CH3),
H 7.08, N 12.65.
32.9 (N1-CH3), 37.7 (C-2’), 49.8 (NH-CH2), 95.4 (C-5),
127.3 (C-4”’), 127.6 (C-2”’), 127.8 (C-3”’), 128.4 (C-2”),
128.6 (C-3”), 133.1 (C-4”), 136.5 (C-1”), 138.8 (C-1”’),
151.7 (C-6), 152.9 (C-2), 162.5 (C-4), 200.0 (C-3’). – EI-
MS: m/z = 377 [M+] (4), 91 (100). – C22H23N3O3 (377.45):
calcd. C 70.01, H 6.14, N 11.13; found C 69.94, H 6.18,
N 11.15.
5-[3-(4-Bromophenyl)-3-oxopropyl]-1,3-dimethyl-6-propyl-
aminouracil (20c)
◦
M. p. 162 C (EtOH); yield 700 mg (43%). – IR: ν =
3306 (NH), 1685 (C=O), 1640 (C=O), 1601 (C=C) cm−1. –
1H NMR (300 MHz, [D6]-DMSO): δ = 0.88 (t, J = 7.4 Hz,
3H, 3”’-H), 1.55 (sext, J = 7.3 Hz, 2H, 2”’-H), 2.66 (t,
J = 7.3 Hz, 2H, 1’-H), 3.00 (t, J = 7.0 Hz, 2H, 1”’-H),
3.13 (t , J = 4.7 Hz, 2’-H), 3.13 (s, 3H, N3-CH3), 3.31
(s, 3H, N1-CH3), 5.57 (d, J = 6.4 Hz, 1H, NH), 7.72 (dt,
J = 8.6 Hz, J = 2.1 Hz, 2H, 3”-H), 7.89 (dt, J = 8.6 Hz,
J = 2.1 Hz, 2H, 2”-H). – 13C NMR (75 MHz, [D6]-DMSO):
δ = 11.2 (C-3”’), 19.7 (C-1’), 23.1 (C-2”’), 27.6 (N3-CH3),
32.6 (N1-CH3), 37.8 (C-2’), 48.4 (C-1”’), 94.2 (C-5), 127.2
(C-4”), 129.9 (C-2”), 131.7 (C-3”), 135.5 (C-1”), 151.6
(C-2), 153.4 (C-6), 162.5 (C-4), 199.4 (C-3’). – EI-MS:
m/z = 407 [M+, 79Br] (4), 409 [M+, 81Br] (4), 210 (100).
– C18H22N3O3Br (408.30): calcd. C 52.95, H 5.43, N 10.29;
found C 53.04, H 5.66, N 10.67.
6-Benzylamino-5-[3-(4-bromophenyl)-3-oxopropyl]-1,3-di-
methyluracil (21c)
◦
M. p. 140 C (isopropanol); yield 187 mg (41%). – IR:
ν = 1682 (C=O), 1632 (C=O), 1600 (C=C), 1456 (C=C)
cm−1. – 1H NMR (300 MHz, [D6]-DMSO): δ = 2.64 (t,
J = 7.8 Hz, 2H, 1’-H), 2.91 (t, J = 7.4 Hz, 2H, 2’-H), 3.13
(s, 3H, N3-CH3), 3.38 (s, 3H, N1-CH3), 4.25 (d, J = 7.0 Hz,
2H, NH-CH2), 6.09 (t, J = 7.0 Hz, 1H, NH), 7.28 (mc, 5H,
Ar-H”’), 7.71 (dt, J = 8.6 Hz, J = 2.1 Hz, 2H, 3”-H), 7.81
(dt, J = 8.6 Hz, J = 2.1 Hz, 2H, 2”-H). – 13C NMR (75 MHz,
[D6]-DMSO/CDCl3): δ = 19.4 (C-1’), 27.6 (N3-CH3), 32.9
(N1-CH3), 37.7 (C-2’), 49.8 (NH-CH2), 98.3 (C-5), 127.1
(C-4”), 127.3 (C-4”’), 127.6 (C-2”’), 128.4 (C-3”’), 129.8
(C-2”), 131.7 (C-3”), 135.5 (C-1”), 138.8 (C-1”’), 151.7
(C-2), 152.9 (C-6), 162.4 (C-4), 199.2 (C-3’). – EI-MS:
m/z = 455 [M+, 79Br] (1), 457 [M+, 81Br] (1), 91 (100).
– C22H22N3O3Br (456.34): calcd. C 57.90, H 4.86, N 9.21;
found C 57.80, H 5.17, N 9.56.
5-[3-(4-Methoxyphenyl)-3-oxopropyl]-1,3-dimethyl-6-prop-
ylaminouracil (20d)
◦
M. p. 131 – 132 C (isopropanol); yield 400 mg (28%).
– IR: ν = 3326 (NH), 1694 (C=O), 1672 (C=O), 1636
(C=O), 1610 (C=C) cm−1. – 1H NMR (300 MHz, [D6]-
DMSO): δ = 0.90 (t, J = 7.4 Hz, 3H, 3”’-H), 1.56 (sext,
J = 7.4 Hz, 2H, 2”’-H), 2.66 (t, J = 7.4 Hz, 2H, 1’-H), 3.00
(q, J = 6.7 Hz, 2H, 1”’-H), 3.08 (t, J = 7.4 Hz, 2H, 2’-H),
3.15 (s, 3H, N3-CH3), 3.31 (s, 3H, N1-CH3), 3.84 (s, 3H,
O-CH3), 5.62 (t, J = 6.5 Hz, 1H, NH), 7.03 (mc, 2H, 3”-H),
7.96 (mc, 2H, 2”-H). – 13C NMR (75 MHz, [D6]-DMSO):
δ = 11.2 (C-3”’), 19.8 (C-1’), 23.1 (C-2”’), 27.5 (N3-CH3),
32.5 (N1-CH3), 37.3 (C-2’), 48.4 (C-1”’), 55.4 (O-CH3),
94.6 (C-5), 113.8 (C-3”), 129.4 (C-1”), 130.1 (C-2”), 151.6
(C-6), 153.3 (C-2), 162.4 (C-4”), 163.0 (C-4), 198.5 (C-3’).
– EI-MS: m/z = 359 [M+] (9), 197 (100). – C19H25N3O4
(359.43): calcd. C 63.49, H 7.01, N 11.69; found C 63.55,
H 7.07, N 11.58.
6-Anilino-1,3-dimethyl-5-(3-oxo-3-phenylpropyl)uracil
(22a)
◦
M. p. 200 C (isopropanol); yield 680 mg (47%). – IR:
ν = 1704 (C=O), 1682 (C=O), 1640 (C=O), 1606 (C=C)
1
cm−1. – H NMR (300 MHz, [D6]-DMSO): δ = 2.64 (mc,
2H, 1’-H), 3.11 (mc, 2H, 2’-H), 3.17 (s, 3H, N3-CH3), 3.25
(s, 3H, N1-CH3), 6.81 (d, J = 7.5 Hz, 2H, 2”’-H), 6.90 (t, J =
7.4 Hz, 1H, 4”’-H), 7.25 (t, J = 7.5 Hz, 2H, 3”’-H), 7.46 (t,
J = 7.5 Hz, 2H, 3”-H), 7.59 (tt, J = 7.4 Hz, J = 1.8 Hz, 1H,
4”-H), 7.87 (d, J = 7.0 Hz, 2H, 2”-H), 8.30 (s, 1H, NH). –
13C NMR (75 MHz, [D6]-DMSO/CDCl3): δ = 20.1 (C-1’),
27.7 (N3-CH3), 31.5 (N1-CH3), 37.3 (C-2’), 103.5 (C-5),
115.8 (C-2”’), 120.6 (C-4”’), 127.6 (C-3”), 128.4 (C-2”),
129.3 (C-3”’), 132.9 (C-4”), 136.2 (C-1”), 143.0 (C-6), 146.7
(C-1”’), 151.5 (C-2), 162.8 (C-4), 199.6 (C-3’). – EI-MS:
6-Benzylamino-1,3-dimethyl-5-(3-oxo-3-phenylpropyl)-
uracil (21a)
◦
M. p. 107 C (isopropanol); yield 700 mg (46%). – IR: m/z = 363 [M+] (24), 258 (100). – C21H21N3O3 (363.42):
ν = 1684 (C=O), 1670 (C=O), 1634 (C=O), 1616 (C=C) calcd. C 69.41, H 5.82, N 11.56; found C 69.54, H 5.87,
cm−1. – 1H NMR (300 MHz, [D6]-DMSO): δ = 2.54 (t, N 11.76.
Unauthenticated
Download Date | 5/24/16 3:19 PM