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S. A. Rocco et al.
PAPER
4-N-(4 -Methoxy-phenyl)amino-6,7-dimethoxyquina-zoline
Anal. Calcd for C16H14N3O2Br.HCl: C, 48.45; H, 3.81; N, 10.59.
Found: C, 48.85; H, 3.54; N, 10.64.
(18f )
Yield: 0.101 g (0.291 mmol, 65.2%); mp 205–207 °C.
4-N-(4 -Bromo-phenyl)amino-6,7-dimethoxyquinazoline (18d )
Yield: 0.126 g (0.318 mmol, 71.2%); mp 277–279 °C.
IR (KBr): 3403.2 (NH), 2948.6 (aromatic CH), 1634.8 (aromatic
CN), 1516.3 (aromatic CC), 1243.1 (COC), 861.9–774.4 (CH)
cm–1.
1H NMR [500 MHz, (CD3)2SO]: = 11.52 (s, 1 H, NH), 8.76 (s, 1
H, H-2), 8.38 (s, 1 H, H-5), 7.59 (d, 3J = 9.0 Hz, 2 H, H-2 , H-6 ),
7.38 (s, 1 H, H-8), 7.02 (d, 3J = 9.5 Hz, 2 H, H-3 , H-5 ), 4.01 (s, 3
H, H-6a), 3.97 (s, 3 H, H-7a), 3.80 (s, 3 H, H-7 ).
IR (KBr): 3448.6 (NH), 3144.4 (aromatic CH), 1629.5 (aromatic
CN), 1516.3 (aromatic CC), 1284.3 (COC), 866.9–774.4 (CH),
501.1 (CBr) cm–1.
1H NMR [500 MHz, (CD3)2SO]: = 11.19 (s, 1 H, NH), 8.88 (s, 1
H, H-2), 8.22 (s, 1 H, H-5), 7.70 (high s, 4 H, H-2 , H-3 , H-5 , H-
6 ), 7.32 (s, 1 H, H-8), 4.04 (s, 3 H, H-6a), 4.02 (s, 3 H, H-7a).
MS (EI): m/z (%) = 311.1 (100) [M+·], 310.1 (64.9) [M – H]+.
MS (EI): m/z (%) = 358.9 (81.1) [M+·], 358.9 (100) [M – H]+.
Anal. Calcd for C17H17N3O3·HCl: C, 58.71; H, 5.22; N, 12.08.
Found: C, 58.68; H, 5.03; N, 12.10.
Anal. Calcd for C16H14N3O2Br·HCl: C, 48.45; H, 3.81; N, 10.59.
Found: C, 48.38; H, 3.61; N, 10.54.
4-N-(3 -Methyl-phenyl)amino-6,7-dimethoxyquinazoline
(18g)11
4-N-(3 -Iodo-phenyl)amino-6,7-dimethoxyquinazoline (18e)
Yield: 0.119 g (0.268 mmol, 60.4%); mp 218–220 °C.7
Yield: 0.075 g (0.226 mmol, 50.7%); mp 221–223 °C.11
IR (KBr): 3417.6 (NH), 3025.9 (aromatic CH), 1629.5 (aromatic
CN), 1516.3 (aromatic CC), 1279.3 (COC), 877.3–779.4 (CH), 600
(CI) cm–1.
IR (KBr): 3417.6 (NH), 3007.6 (aromatic CH), 1634.8 (aromatic
CN), 1511.0 (aromatic CC), 1279.3 (COC), 775.0 (CH) cm–1.
1H NMR [500 MHz, (CD3)2SO]: = 11.24 (s, 1 H, NH), 8.78 (s, 1
H, H-2), 8.29 (s, 1 H, H-5), 7.50 (signal superposition, 2 H, H-2 , H-
5 ), 7.36 (signal superposition, 2 H, H-8, H-6 ), 7.14 (d, 3J = 8.0 Hz,
1 H, H-4 ), 4.02 (s, 3 H, H-6a), 3.99 (s, 3 H, H-7a), 2.37 (s, 3 H, H-
7 ).
1H NMR [500 MHz, (CD3)2SO]: = 11.50 (s, 1 H, NH), 8.85 (s, 1
4
H, H-2), 8.39 (s, 1 H, H-5), 8.15 (t, J = 1.5 Hz, 1 H, H-2 ), 7.81
(ddd, 3J = 8.2 Hz, 4J = 1.5 Hz, 4J = 1.0 Hz, 1 H, H-4 ), 7.70 (ddd,
3J = 8.0 Hz, 4J = 1.5 Hz, 4J = 1.0 Hz, 1 H, H-6 ), 7.39 (s, 1 H, H-8),
7.27 (t, 3J = 8.0 Hz, 1 H, H-5 ), 4.03 (s, 3 H, H-6a), 4.00 (s, 3 H, H-
7a).
MS (EI): m/z (%) = 295.0 (87.4) [M+·], 294.0 (100) [M – H]+.
Anal. Calcd for C17H17N3O2·HCl: C, 61.54; H, 5.47; N, 12.66.
Found: C, 61.96; H, 5.55; N, 12.96.
MS (EI): m/z (%) = 406.9 (95.0) [M+·], 405.9 (100) [M – H]+.
Anal. Calcd for C16H14N3O2I·HCl: C, 43.31; H, 3.41; N, 9.47.
Found: C, 43.26; H, 3.35; N, 9.26.
4-N-(4 -Methyl-phenyl)amino-6,7-dimethoxyquinazoline (18g )
Yield: 0.096 g (0.290 mmol, 64.9%); mp 227–229 °C.
4-N-(4 -Iodo-phenyl)amino-6,7-dimethoxyquinazoline (18e )
Yield: 0.121 g (0.273 mmol, 61.4%); mp 266–269 °C.
IR (KBr): 3418.6 (NH), 2948.6 (CH), 1634.8 (aromatic CN),
1506.0 (aromatic CC), 1279.3 (COC), 866.9–779.4 (CH) cm–1.
IR (KBr): 3397.0 (NH), 3031.2 (aromatic CH), 1634.8 (aromatic
CN), 1516.3 (aromatic CC), 1289.6 (COC), 872.3–779.4 (CH),
501.1 (CI) cm–1.
1H NMR [500 MHz, (CD3)2SO]: = 11.50 (s, 1 H, NH), 8.83 (s, 1
H, H-2), 8.38 (s, 1 H, H-5), 7.82 (d, 3J = 8.5 Hz, 2 H, H-3 , H-5 ),
7.58 (d, 3J = 8.5 Hz, 2 H, H-2 , H-6 ), 7.37 (s, 1 H, H-8), 4.02 (s, 3
H, H-6a), 4.00 (s, 3 H, H-7a).
1H NMR [500 MHz, (CD3)2SO]: = 11.26 (s, 1 H, NH), 8.75 (s, 1
H, H-2), 8.30 (s, 1 H, H-5), 7.57 (d, 3J = 8.3 Hz, 2 H, H-2 , H-6 ),
7.36 (s, 1 H, H-8), 7.28 (d, 3J = 8.3 Hz, 2 H, H-3 , H-5 ), 4.01 (s, 3
H, H-6a), 3.98 (s, 3 H, H-7a), 2.35 (s, 3 H, H-7 ).
MS(EI): m/z (%) = 295.1 (85.1) [M+·], 294.1 (100) [M – H]+.
Anal. Calcd for C17H17N3O2·HCl: C, 61.54; H, 5.47; N, 12.66.
Found: C, 61.27; H, 5.53; N, 12.42.
MS (EI): m/z (%) = 407.0 (100) [M+·], 406.0 (93.2) [M – H]+.
Anal. Calcd for C16H14N3O2I·HCl: C, 43.31; H, 3.41; N, 9.47.
Found: C, 43.44; H, 3.42; N, 9.28.
4-N-(3 -Acetyl-phenyl)amino-6,7-dimethoxyquinazoline (18h)
Yield: 0.097 g (0.270 mmol, 60.6%); mp 219–221 °C.
IR (KBr): 3427.9 (NH), 3036.2 (aromatic CH), 1681.1 (C=O),
1634.8 (aromatic CN), 1516.3 (aromatic CC), 1279.3 (COC),
882.5–779.4 (CH) cm–1.
4-N-(3 -Methoxy-phenyl)amino-6,7-dimethoxyquinazoline
(18f)
Yield: 0.094 g (0.270 mmol, 60.6%); mp 216–218 °C.
1H NMR [500 MHz, (CD3)2SO]: = 11.49 (s, 1 H, NH), 8.79 (s, 1
IR (KBr): 3438.3 (NH), 3005.3 (aromatic CH), 1634.8 (aromatic
CN), 1495.7 (aromatic CC), 1279.3 (COC), 872.2–774.4 (CH)
cm–1.
1H NMR [500 MHz, (CD3)2SO]: = 11.39 (s, 1 H, NH), 8.81 (s, 1
H, H-2), 8.37 (s, 1 H, H-5), 7.39 (s, 1 H, H-8), 7.39 (t, 3J = 8.0 Hz,
1 H, H-5 ), 7.35 (t, 4J = 2.0 Hz, 1 H, H-2 ), 7.31 (ddd, 3J = 8.0 Hz,
4J = 2. 0 Hz, 4J = 1.0 Hz, 1 H, H-6 ), 6.90 (ddd, 3J = 8.2 Hz, 4J = 2.5
Hz, 4J = 1.0 Hz, 1 H, H-4 ), 4.03 (s, 3 H, H-6a), 4.00 (s, 3 H, H-7a),
3.80 (s, 3 H, H-7 ).
4
H, H-2), 8.45 (s, 1 H, H-5), 8.34 (t, J = 2.0 Hz, 1 H, H-2 ), 8.10
4
4
(ddd, 3J = 8.1 Hz, J = 2.1 Hz, J = 1.1 Hz, 1 H, H-6 ), 7.87 (ddd,
3J = 7.7 Hz, 4J = 1.7 Hz, 4J = 1.1 Hz, 1 H, H-4 ), 7.62 (t, 3J = 8.0 Hz,
1 H, H-5 ), 7.42 (s, 1 H, H-8), 4.05 (s, 3 H, H-6a), 3.99 (s, 3 H, H-
7a), 2.63 (s, 3 H, H-8 ).
MS (EI): m/z (%) = 323.0 (83.9) [M+·], 322.0 (100) [M – H]+.
Anal. Calcd for C18H17N3O3·HCl: C, 60.09; H, 5.04; N, 11.68.
Found: C, 59.07; H, 4.69; N, 11.72.
MS (EI): m/z (%) = 311.0 (79.3) [M+·], 310.0 (100) [M – H]+.
4-N-(4 -Acetyl-phenyl)amino-6,7-dimethoxyquinazoline (18h )
Anal. Calcd for C17H17N3O3.HCl: C, 58.71; H, 5.22; N, 12.08.
Found: C, 58.52; H, 5.00; N, 12.17.
Yield: 0.110 g (0.306 mmol, 68.7%); mp 218–220 °C.
IR (KBr): 3412.3 (NH), 2995.2 (aromatic CH), 1670.8 (C=O),
1634.8 (aromatic CN), 1516.3 (aromatic CC), 1279.3 (COC),
872.2–779.4 (CH) cm–1.
Synthesis 2004, No. 3, 429–435 © Thieme Stuttgart · New York