6
of 9
AGRE ET AL.
|
(
400 MHz, DMSO‐d6): δ (ppm) 10.33 (s, 1H, 3‐NH), 9.07 (s, 1H,
‐NH), 7.20 (t, J = 7.6 Hz, 2H, ArH), 6.99 (t, J = 8.4 Hz, 2H, ArH), 6.15
s, 2H, NH ), 4.87 (s, 1H, CH), 2.29 (s, 3H, COCH ), 2.00 (s, 3H, CH ).
HPLC: retention time (RT): 2.983 min.
5‐(3,4‐Dimethoxyphenyl)‐6‐acetyl‐2‐amino‐7‐methyl‐5,8‐
dihydropyrido[2,3‐d]pyrimidin‐4(3H)‐one (2l)
8
(
2
3
3
Yellow solid; yield: 81%; mp > 250°C. IR (KBr): υmax 3656.10; 3159.74;
−1
1
2946.2; 2888.3; 1673.3; 1644.4; 1602.71; 1520.06 cm
.
H NMR
(400 MHz, DMSO‐d6): δ (ppm): 10.32 (s, 1H, 3‐NH), 8.99 (s, 1 H, 8‐NH),
6
.91 (s, 1 H, ArH), 6.74 (d, J = 8.4 Hz, 1H, ArH), 6.64 (d, J = 7.2 Hz,
H, ArH), 6.21 (s, 2H, NH ), 4.82 (s, 1H, CH), 3.63 (s, 6H, OCH ), 2.29
), 1.99 (s, 3H, CH ). HPLC: retention time (RT): 2.783 min.
5
‐(4‐Bromophenyl)‐6‐acetyl‐2‐amino‐7‐methyl‐5,8‐dihydropyrido‐
2,3‐d]pyrimidin‐4(3H)‐one (2g)
Yellow solid; yield: 77%; mp > 250°C. IR (KBr):
1
2
3
[
(s, 3H, COCH
3
3
υ
max 3337.79;
−1
3166.34; 2941.23; 1677.4; 1652.6; 1603.07; 1521.56 cm .
5
‐(3,4,5‐Trimethoxyphenyl)‐6‐acetyl‐2‐amino‐7‐methyl‐5,8‐
1
H NMR (400 MHz, DMSO‐d6): δ (ppm) 10.35 (s, 1H, 3‐NH), 9.09
s, 1H, 8‐NH), 7.35 (d, J = 8.0 Hz, 2H, ArH), 7.15 (d, J = 8.0 Hz, 2H,
dihydropyrido[2,3‐d]pyrimidin‐4(3H)‐one (2m)
(
Yellow solid; yield: 74%; mp > 250°C. IR (KBr): υmax 3338.8; 3164.81;
ArH), 6.25 (s, 2H, NH
2
), 4.85 (s, 1H, CH), 2.29 (s, 3H, COCH
3
), 2.00
−1
1
3
033; 2946.2; 1677.4; 1656.8; 1601.84; 1520.97 cm
400 MHz, DMSO‐d6): (ppm) 10.34 (s, 1H, 3‐NH), 9.04
s, 1H, 8‐NH), 6.51 (s, 2H, ArH), 6.24 (s, 2H, NH ), 4.86 (s, 1H, CH),
.64 (s, 6H, OCH ), 3.56 (s, 3H, OCH ), 2.31 (s, 3H, COCH ), 2.02
s, 3H, CH ). HPLC: retention time (RT): 2.792 min.
.
H NMR
(s, 3H, CH ). HPLC: retention time (RT): 3.183 min.
3
(
(
δ
2
3
3
3
3
5
‐(4‐Trifluoromethylphenyl)‐6‐acetyl‐2‐amino‐7‐methyl‐5,8‐
dihydropyrido[2,3‐d]pyrimidin‐4(3H)‐one (2h)
Yellow solid; yield: 80%; mp > 250°C. IR (KBr): υmax 3442; 3146.96;
(
3
5‐(4‐Hydroxyphenyl)‐6‐acetyl‐2‐amino‐7‐methyl‐5,8‐dihydropyrido‐
−1 1
2
882.26; 1665.85; 1627.8; 1603; 1572.74 cm
DMSO‐d6): δ (ppm) 10.35 (s, 1H, 3‐NH), 9.15 (s, 1H, 8‐NH), 7.53
d, J = 8.0 Hz, 2H, ArH), 7.41 (d, J = 8.0 Hz, 2H, ArH), 6.27 (s, 2H, NH ),
.97 (s, 1H, CH), 2.31 (s, 3H, COCH ), 2.03 (s, 3H, CH ). HPLC: retention
time (RT): 3.275 min.
. H NMR (400 MHz,
[2,3‐d]pyrimidin‐4(3H)‐one (2n)
Yellow solid; yield: 78%; mp > 250°C. IR (KBr): υmax 3337.20;
(
2
−
1
3164.50; 2942.79; 1677.4; 1660.9; 1594.55; 1523.49 cm .
4
3
3
1
H NMR (400 MHz, DMSO‐d6): δ (ppm) 10.32 (s, 1H, 3‐NH), 9.05
s, 1H, 8‐NH), 8.97 (s, 1H, OH), 6.97 (d, J = 8.0 Hz, 2H, ArH), 6.56
(
(
d, J = 8.0 Hz, 2H, ArH), 6.21 (s, 2H, NH
2
), 4.75 (s, 1H, CH), 2.31 (s, 3H,
COCH
3
), 1.98 (s, 3H, CH ). HPLC: retention time (RT): 2.642 min.
3
5
‐(4‐Methylphenyl)‐6‐acetyl‐2‐amino‐7‐methyl‐5,8‐dihydropyrido‐
2,3‐d]pyrimidin‐4(3H)‐one (2i)
Yellow solid; yield: 79%; mp > 250°C. IR (KBr): υmax 3156.42; 2937.9;
[
5‐(4‐Hydroxy‐3‐methoxyphenyl)‐6‐acetyl‐2‐amino‐7‐methyl‐5,8‐
dihydropyrido[2,3‐d]pyrimidin‐4(3H)‐one (2o)
−
1
1
1673.3; 1650.24; 1583.34; 1518.51 cm
.
H
NMR (400 MHz,
Yellow solid; yield: 72%; mp > 250°C. IR (KBr): υmax 3524.7; 3337.28;
DMSO‐d6):
δ
(ppm) 10.28 (s, 1H, 3‐NH), 9.00 (s, 1H,
−
1 1
3166.73; 2943.99; 1681.5; 1660.9; 1601.14; 1519.04 cm
. H NMR
8
‐NH), 7.06 (d, J = 8.0 Hz, 2H, ArH), 6.98 (d, J = 7.6 Hz, 2H, ArH), 6.27
s, 2H, NH ), 4.82 (s, 1H, CH), 2.28 (s, 3H, COCH ), 2.17 (s, 3H, CH
.98 (s, 3H, 7‐CH ). HPLC: retention time (RT): 3.033 min.
(400 MHz, DMSO‐d6): δ (ppm) 10.34 (s, 1H, 3‐NH), 8.97 (s, 1H, OH),
(
2
3
3
)
8
.62 (s, 1H, 8‐NH), 6.86 (s, 1H, ArH), 6.56 (d, J = 7.6 Hz, 1H, ArH),
.52 (d, J = 8.0 Hz, 1H, ArH), 6.22 (s, 2H, NH ), 4.78 (s, 1H, CH), 3.64
), 2.28 (s, 3H, COCH ), 1.99 (s, 3H, CH ). HPLC:
retention time (RT): 2.650 min.
1
3
6
2
(s, 3H, OCH
3
3
3
5
‐(4‐Thiomethylphenyl)‐6‐acetyl‐2‐amino‐7‐methyl‐5,8‐
dihydropyrido[2,3‐d]pyrimidin‐4(3H)‐one (2j)
Yellow solid; yield: 82%; mp > 250°C. IR (KBr): υmax 3643.34; 3016.71;
5‐(3‐Hydroxy‐4‐methoxyphenyl)‐6‐acetyl‐2‐amino‐7‐methyl‐5,8‐
−
1
1
dihydropyrido[2,3‐d]pyrimidin‐4(3H)‐one (2p)
2
884.33; 1678.87; 1653.9; 1586.81; 1520.55 cm . H NMR (400 MHz,
DMSO‐d6): (ppm) 10.31 (s, 1H, 3‐NH), 9.04 (s, 1H,
‐NH), 7.09 (d, J = 8.0 Hz, 2H, ArH), 7.12 (d, J = 8.0 Hz, 2H, ArH), 6.22
), 4.82 (s, 1H, CH), 2.37 (s, 3H, 3‐CH ), 2.28 (s, 3H, COCH ),
.99 (s, 3H, 7‐CH ). HPLC: retention time (RT): 3.067 min.
Yellow solid; yield: 71%; mp > 250°C. IR (KBr): υmax 3487.5; 3334.6;
δ
−
1
1
3
173.51; 2942; 1673.3; 1648.5; 1598.86; 1515.72 cm
400 MHz, DMSO‐d6): (ppm) 10.30 (s, 1H, 3‐NH), 9.05
s, 1H, 8‐NH), 8.97 (s, 1H, OH), 8.69 (s, 1H, NH), 6.56–6.70 (m, 3H,
ArH), 6.20 (s, 2H, NH ), 4.73 (s, 1H, CH), 3.64 (s, 3H, OCH ), 2.27 (s, 3H,
COCH ), 1.98 (s, 3H, CH ). HPLC: retention time (RT): 3.000 min.
.
H NMR
8
(
δ
(s, 2H, NH
2
3
3
(
1
3
2
3
3
3
5
‐(4‐Methoxyphenyl)‐6‐acetyl‐2‐amino‐7‐methyl‐5,8‐dihydropyrido‐
2,3‐d]pyrimidin‐4(3H)‐one (2k)
Yellow solid; yield: 73%; mp > 250°C. IR (KBr):
098.27; 2884.52; 1674.7; 1654.18; 1589.33; 1520.60 cm
NMR (400 MHz, DMSO‐d6): δ (ppm) 10.30 (s, 1H, 3‐NH), 9.00 (s, 1H,
‐NH), 7.09 (d, J = 8.4 Hz, 2H, ArH), 6.74 (d, J = 8.4 Hz, 2H, ArH), 6.20
s, 2H, NH ), 4.80 (s, 1H, CH), 3.64 (s, 3H, OCH ), 2.28 (s, 3H,
), 1.98 (s, 3H, CH ). HPLC: retention time (RT): 2.908 min.
[
5‐(3‐Hydroxyphenyl)‐6‐acetyl‐2‐amino‐7‐methyl‐5,8‐dihydropyrido‐
[2,3‐d]pyrimidin‐4(3H)‐one (2q)
υ
max 3649.90;
−1
1
3
.
H
Yellow solid; yield: 72%; mp > 250°C. IR (KBr): υmax 3298.42; 3198.3;
−1
1
2839.34; 1662.99; 1605.83; 1513.29 cm
.
H NMR (400 MHz,
8
DMSO‐d6): δ (ppm) 10.32 (s, 1H, 3‐NH), 9.10 (s, 1H, OH), 9.02
(s, 1H, 8‐NH), 6.94 (t, J = 8.0 Hz, 1H, ArH), 6.63 (d, J = 8.4 Hz, 2H, ArH),
(
2
3
COCH
3
3
2
6.44 (d, J = 8.0 Hz, 2H, ArH), 6.22 (s, 2H, NH ), 4.79 (s, 1H, CH), 3.30