Month 2018
The Pyrido[2,3-d]pyrimidine Nucleus Represent in Many Biologically Active
Compounds which Includes Antitumor
Ar─H), 8.29 (s, 1H, Ar─H), 8.35–8.39 (m, 2H, Ar─H);
3.89 (s, 3H, ─OCH ), 4.09 (s, 2H, ─CH ), 6.98–7.01 (d,
3
2
+
ESI-MS: 451 (M +H); HRMS: m/z Calcd for
2H, J = 8.99 Hz), 7.54–7.60 (m, 5H, Ar─H), 8.23 (s, 1H,
Ar─H), 8.34–8.38 (m, 2H, Ar─H); ESI-MS: 479
+
C H F N O (M +H): 451.17162. Found: 451.17212.
2
5 22 3 4
+
+
4
,7-Diphenyl-2-((thiomorpholino)methyl)-5-(trifluoromethyl)
(M +H); HRMS: m/z Calcd for C H F N O (M +H):
27 26 3 4
pyrido[2,3-d]pyrimidine (7d). Yield: 90 mg (64.37%), mp
4
79.20532. Found: 479.20297.
4-(4-Methoxyphenyl)-7-phenyl-2-(piperazin-1-ylmethyl)-5-
À1
1
1
3
3
92°C. IR (KBr) cm : 1596 (C═C); H NMR (CDCl3,
00 MHz): δ 2.73–2.79 (t, 4H, ─CH2, J = 5.28 Hz),
.00–3.05 (t, 4H, ─CH2, J = 5.28 Hz), 4.14 (s, 2H,
(trifluoromethyl)pyrido[2,3-d]pyrimidine (7j). Yield: 90 mg
À1
(62.63%), mp 174°C. IR (KBr) cm : 3422 (NH), 1602
1
─
CH ), 7.47–7.63 (m, 8H, Ar─H), 8.29 (s, 1H, Ar─H),
(C═C). H NMR (CDCl3, 300 MHz): δ 2.72–2.79 (t, 4H,
2
+
8.35–8.40 (m, 2H, Ar─H); ESI-MS: 467 (M +H);
─CH2, J = 5.28 Hz), 2.91 (s, 1H, NH), 2.96–3.02 (t, 4H,
+
HRMS: m/z Calcd for C H F N S (M +H): 467.15118.
─CH2, J = 5.28 Hz), 3.90 (s, 3H, ─OCH ), 4.12 (s,
3
2
5 22 3 4
Found: 467.14849.
2H, ─CH ), 6.98–7.04 (m, 2H, Ar─H) 7.54–7.61 (m, 5H,
2
2-((4-Methylpiperazin-1-yl)methyl)-4,7-diphenyl-5-(trifluoromethyl)
Ar─H), 8.26 (s, 1H, Ar─H), 8.35–8.39 (m, 2H, Ar─H);
+
pyrido[2,3-d]pyrimidine (7e).
Yield: 95 mg (68.39%), mp
ESI-MS: 480 (M +H); HRMS: m/z Calcd for
À1
1
+
174°C. IR (KBr) cm : 1599 (C═C); H NMR (CDCl3,
C H F N O (M +H): 480.20057. Found: 480.19815.
2
6 25 3 5
3
00 MHz): δ 2.30 (s, 3H, ─CH ), 2.49–2.60 (m, 4H,
2-(Morpholinomethyl)-4-(4-methoxyphenyl)-7-phenyl-5-
3
─
CH ), 2.76–2.89 (m, 4H, ─CH ), 4.15 (s, 2H, ─CH ),
(trifluoromethyl)pyrido[2,3-d]pyrimidine (7k). Yield: 100 mg
2
2
2
À1
1
7.46–7.61 (m, 8H, Ar─H), 8.27 (s, 1H, Ar─H), 8.35–8.39
(69.44%), mp 172°C. IR (KBr) cm : 1600 (C═C). H
NMR (CDCl3, 300 MHz): δ 2.71–2.83 (m, 4H, ─CH ),
3.75–3.83 (m, 4H, ─CH ), 3.89 (s, 3H, ─OCH ), 4.13 (s,
2H, ─CH ), 6.96–7.02(d, 2H, Ar─H, J = 7.99 Hz), 7.51–
+
(m, 2H, Ar─H); ESI-MS: 464 (M +H); HRMS: m/z Calcd
2
+
for C H F N (M +H): 464.20566. Found: 464.20313.
2
3
26 25 3 5
3-(4-((4,7-Diphenyl-5-(trifluoromethyl)pyrido[2,3-d]pyrimidin-2-yl)
2
methyl)piperazin-1-yl)propan-1-ol (7f). Yield: 68 mg (45.97%),
mp 219°C. IR (KBr) cm : 3491 (─OH), 1601 (C═C); H
NMR (CDCl3, 300 MHz): δ 2.54–2.60 (t, 2H, ─CH2,
7.63 (m, 5H, Ar─H), 8.29 (s, 1H, Ar─H), 8.34–8.41 (m,
À1
1
+
2H, Ar─H); ESI-MS: 481 (M +H); HRMS: m/z Calcd for
+
C H F N O (M +H): 481.18201. Found: 481.18201.
26
24 3 4 2
J = 5.09 Hz), 2.60 (m, 4H, ─CH ), 2.75–2.89 (m, 4H,
4-(4-Methoxyphenyl)-7-phenyl-2-((thiomorpholino)methyl)-5-
2
─
CH ), 3.59–3.64 (t, 2H, ─CH J = 5.09 Hz), 4.15 (s, 2H,
(trifluoromethyl)pyrido[2,3-d]pyrimidine(7l). Yield: 110 mg
2
2,
À1
1
─
CH ), 7.45–7.64 (m, 8H, Ar─H), 8.29 (s, 1H, Ar─H),
.35–8.40 (m, 2H, Ar─H); ESI-MS: 494 (M +H); HRMS:
(73.92%), mp: 144°C. IR (KBr) cm : 1600 (C═C) H
NMR (CDCl3, 500 MHz): δ 2.74–2.78 (t, 4H, ─CH2,
J = 4.99 Hz), 3.01–3.05 (t, 4H, ─CH2, J = 4.99 Hz), 3.90
2
+
8
+
m/z Calcd for C H F N O (M +H): 494.21622. Found:
27 27 3 5
494.21375.
(s, 3H, ─OCH
3
), 4.14 (s, 2H, ─CH ), 6.99–7.03 (d, 2H,
2
4
,7-Diphenyl-2-((4-phenylpiperazin-1-yl)methyl)-5-(trifluoromethyl)
Ar─H, J = 8.99 Hz), 7.54–7.61 (m, 5H, Ar─H), 8.25 (s,
1H, Ar─H), 8.35–8.38 (m, 2H, Ar─H); ESI-MS: 497
pyrido[2,3-d]pyrimidine (7g).
18°C. IR (KBr) cm : 1599 (C═C); H NMR (CDCl
Yield: 135 mg (85.71%), mp
À1
1
+
+
2
(M +H); HRMS: m/z Calcd for C H F N OS (M +H):
3,
26 24 3 4
3
00 MHz): δ 2.91–2.99 (m, 4H, ─CH ), 3.25–3.33 (m, 4H,
497.15934. Found: 497.15936.
2
─
CH ), 4.22 (s, 2H, ─CH ), 6.82–6.88 (t, 1H, Ar─H
2-((4-Methylpiperazin-1-yl)methyl)-4-(4-methoxyphenyl)-7-
2
2
,
J = 7.36 Hz), 6.91–6.98 (d, 2H, Ar─H, J = 7.93), 7.22–7.30
phenyl-5-(trifluoromethyl)pyrido[2,3-d]pyrimidine (7m). Yield:
À1
(m, 2H, Ar─H), 7.45–7.63 (m, 8H, Ar─H), 8.29 (s, 1H,
95 mg (64.23%), mp 215°C, IR (KBr) cm : 1601 (C═C)
+
1
Ar─H), 8.35–8.41 (m, 2H, Ar─H); ESI-MS: 526 (M +H);
HRMS: m/z Calcd for C H F N (M +H): 526.22131.
Found: 526.21948.
H NMR (CDCl3, 300 MHz): δ 2.30 (s, 3H, ─CH
), 2.72–3.00 (m, 4H, ─CH
), 4.15 (s, 2H, ─CH
3
),
),
+
2.47–2.62 (m, 4H, ─CH
3.90 (s, 3H, ─OCH
31 27 3 5
2
2
), 6.97–7.04 (d,
3
2
4
,7-Diphenyl-2-((4-(pyridin-2-yl)piperazin-1-yl)methyl)-5-
2H, Ar─H, J = 8.68 Hz), 7.52–7.64 (m, 5H, Ar─H), 8.26
(s, 1H, Ar─H), 8.34–8.40 (m, 2H, Ar─H), ESI-MS: 494
(
(
(
trifluoromethyl)pyrido[2,3-d]pyrimidine (7h). Yield: 150 mg
95.05%), mp 192°C. IR (KBr) cm : 2826 (CH ), 1596
C═C); H NMR (CDCl 300 MHz): δ 2.86–2.93 (t, 4H,
À1
+
+
2
(M +H); HRMS: m/z Calcd for C H F N O (M +H):
27 27 3 5
1
3
,
494.21622. Found: 494.21378.
─
CH2, J = 5.28 Hz), 3.60–3.67 (t, 4H, ─CH2,
3-(4-((4-(4-Methoxyphenyl)-7-phenyl-5-(trifluoromethyl)
pyrido[2,3-d]pyrimidin-2-yl)methyl)piperazin-1-yl)propan-1-ol (7n).
J = 5.28 Hz), 4.21 (s, 2H, ─CH ), 6.59–6.68 (m, 2H,
Ar─H), 7.43–7.64 (m, 9H, Ar─H), 8.17–8.21 (m, 1H,
Ar─H), 8.29 (s, 1H, Ar─H), 8.36–8.40 (m, 2H, Ar─H);
2
À1
Yield: 70 mg (44.61%), mp 130°C. IR (KBr) cm : 3415
1
(─OH), 1602 (C═C), H NMR (CDCl3, 300 MHz): δ 2.62–
+
ESI-MS: 527 (M +H); HRMS: m/z Calcd for C H F N
2.67 (t, 2H, ─CH
2.83–2.91 (m, 4H, ─CH
J = 5.57 Hz), 3.90 (s, 3H, ─OCH ), 4.13 (s, 2H, ─CH ),
2
, J = 5.57 Hz), 2.70–2.77 (m, 4H, ─CH
),
2
3
0
26
3
6
+
(M +H): 527.21656. Found: 527.21509.
2
), 3.64–3.69 (t, 2H, ─CH2,
4
-(4-Methoxyphenyl)-7-phenyl-2-(piperidin-1-ylmethyl)-5-
3
2
(trifluoromethyl)pyrido[2,3-d]pyrimidine (7i). Yield: 120 mg
6.98–7.03 (d, 2H, Ar─H, J = 9.29 Hz), 7.52–7.62 (m, 5H,
Ar─H), 8.25 (s, 1H, Ar─H), 8.34–8.38 (m, 2H, Ar─H);
À1
1
(83.68%), mp 159°C. IR (KBr) cm : 1601(C═C). H
+
NMR (CDCl3, 300 MHz): δ 1.43–1.49 (m, 2H, ─CH2),
.63–1.60 (m, 4H, ─CH ), 2.66–2.72 (m, 4H, ─CH ),
ESI-MS: 524(M +H); HRMS: m/z Calcd for C H F N O
28
29 3
5
2
+
1
(M +H): 524.22438. Found: 524.22455.
2
2
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet