ACCEPTED MANUSCRIPT
-1
1
Yellow solid; yield 82%; mp 210-211 ºC; IR (KBr, cm ) ν : 3426, 1645, 1589, 1569; H
max
NMR (500 MHz, CDCl ) δ: 4.48 (dd, J = 14.9 Hz, J = 4.7 Hz, 1H, -CH ), 4.72 (dd, J = 14.9
3
2
Hz, J = 4.7 Hz, 1H, -CH ), 5.11 (s, 2H, NH and H-7), 6.85-6.86 (m, 2H, N-Ar-H ), 7.09 (d, J
2
2,6
=
8.5, 1H, H-6), 7.20-7.24 (m, 3H, N-Ar-H3,4,5), 7.26-7.32 (m, 5H, Ar-H2,3,4,5,6), 7.47 (d, J =
8
4
4
1
.5 Hz, 1H, H-5), 7.51-7.54 (m, 1H, H-3), 7.58-7.61 (m, 1H, H-2), 7.75 (d, J = 8.1 Hz, 1H, H-
1
3
), 8.44 (s, 1H, H-10), 8.52 (d, J = 8.5 Hz, 1H, H-1). C NMR (CDCl , 125 MHz) δ: 40.5,
3
5.3, 95.9, 117.0, 121.9, 123.9, 124.0, 125.8, 126.6, 126.8, 127.0, 127.35, 127.39, 127.9,
28.0, 128.6, 129.6, 133.2, 137.9, 143.5, 143.6, 157.0, 161.2, 161.7. Anal. Calcd for
C H N O (415.49): C, 80.94; H, 5.09; N, 10.11. Found: C, 80.63; H, 5.38; N, 9.86.
28
21
3
5
.3.9. N-(2-Chlorobenzyl)-7-phenyl-7H-benzo[7,8]chromeno[2,3-d]pyrimidin-8-amine (6i)
-1
1
Yellow solid; yield 83%; mp 196-198 ºC; IR (KBr, cm ) ν : 3418, 1650, 1608, 1586; H
max
NMR (500 MHz, CDCl ) δ: 4.63 (dd, J = 15.5 Hz, J = 5.5 Hz, 1H, -CH ), 4.75 (dd, J = 15.5
3
2
Hz, J = 5.5 Hz, 1H, -CH ), 5.11 (s, 1H, H-7), 5.26 (br s, 1H, NH), 5.26 (br s, 1H, NH), 6.84
2
(
d, J = 6.7 Hz, 1H, N-Ar-H ), 7.07 (t, 1H, J = 7.7 Hz, Ar-H ), 7.10 (d, J = 8.5 Hz, 1H, H-6),
6
4
7
.15-7.18 (m, 1H, N-Ar-H ), 7.24-7.26 (m, 1H, N-Ar-H ), 7.30-7.35 (m, 5H, Ar-H
and N-
5
3
2,3,5,6
Ar-H ), 7.46 (d, J = 8.5 Hz, 1H, H-5), 7.50-7.52 (m, 1H, H-3), 7.57-7.60 (m, 1H, H-2), 7.73
4
1
3
(
d, J = 8.1 Hz, 1H, H-4), 8.40 (s, 1H, H-10), 8.51 (d, J = 8.5 Hz, 1H, H-1). C NMR (CDCl ,
3
1
1
1
4
25 MHz) δ: 40.3, 43.1, 96.1, 116.9, 121.9, 123.8, 124.2, 125.7, 126.7, 126.8, 126.9, 127.3,
28.0, 128.7, 128.9, 129.1, 129.4, 129.6, 133.2, 133.3, 135.3, 143.2, 143.3, 143.5, 156.1,
61.0. Anal. Calcd for C H ClN O (449.93): C, 74.74; H, 4.48; N, 9.34. Found: C, 74.99; H,
2
8
20
3
.80; N, 9.63.
5
.3.10. N-Phenethyl-7-phenyl-7H-benzo[7,8]chromeno[2,3-d]pyrimidin-8-amine (6j)
-1
Yellow solid; yield 74%; mp 194-195 ºC; IR (KBr, cm ) νmax: 3426, 1593, 1610, 1570 and
1
1
496; H NMR (500 MHz, CDCl ) δ: 2.73-2.78 (m, 2H, -NCH CH ), 3.70-3.72 (m, 1H, -
3
2
2
NCH ), 3.80-3.83 (m, 1H, -NCH ), 4.87 (s, 1H, H-7), 7.03 (d, J = 8.5 Hz, 1H, H-6), 7.07 (d, J
2
2
=
6.6 Hz, 2H, N-Ar-H ), 7.10-7.12 (m, 3H, N-Ar-H ), 7.23-7.26 (m, 3H, Ar-H and NH),
2,6 3,4,5 3,5
7
.27-7.32 (m, 3H, Ar-H2,4,6), 7.46 (d, J = 8.5 Hz, 1H, H-5), 7.51-7.53 ( m, 1H, H-3), 7.57-7.60
(m, 1H, H-2 ), 7.74 (d, J = 8.1 Hz, 1H, H-4), 8.45 (s, 1H, H-10), 8.50 ( d, J = 8.5 Hz, 1H, H-
1
3
1
1
). C NMR (CDCl , 125 MHz) δ: 111.3, 111.5, 117.2, 121.9, 124.0, 125.7, 126.5, 126.8,
3
27.3, 127.7, 128.7, 129.4, 130.7, 133.2, 138.4, 143.2, 147.8, 149.2, 156.7, 161.2, 161.6.
Anal. Calcd for C H N O (429.51): C, 81.09; H, 5.40; N, 9.78. Found: C, 81.46; H, 5.69; N,
2
9
23
3
9
.99.
1
0