Table 2. Second Series of Quinazoline Derivativesa.
| entry | reactant | R3 (intermediate) | R4 | product (yield %) |
|---|---|---|---|---|
| 1 | 5a | 4-methoxyphenyl (6a) | morpholin-1-yl | 7a (89.8) |
| 2 | 5a | 4-methoxyphenyl (6a) | pyrrolidin-1-yl | 7b (80.2) |
| 3 | 5a | 4-methoxyphenyl (6a) | piperazin-1-yl | 7c (79.6) |
| 4 | 5a | 4-methoxyphenyl (6a) | diethylamino | 7d (40.7) |
| 5 | 5a | 4-fluorophenyl (6b) | morpholin-1-yl | 7e (94.9) |
| 6 | 5a | 4-fluorophenyl (6b) | pyrrolidin-1-yl | 7f (96.6) |
| 7 | 5a | 4-fluorophenyl (6b) | piperazin-1-yl | 7g (90.8) |
| 8 | 5a | 4-fluorophenyl (6b) | diethylamino | 7h (34.7) |
| 9 | 5a | thiophen-2-yl (6c) | morpholin-1-yl | 7i (82.6) |
| 10 | 5a | thiophen-2-yl (6c) | pyrrolidin-1-yl | 7j (87.6) |
| 11 | 5b | 4-methoxyphenyl (6d) | morpholin-1-yl | 7k (90.1) |
| 12 | 5b | 4-methoxyphenyl (6d) | pyrrolidin-1-yl | 7l (91.8) |
| 13 | 5b | 4-methoxyphenyl (6d) | piperazin-1-yl | 7m (84.9) |
| 14 | 5b | 4-methoxyphenyl (6d) | diethylamino | 7n (54.4) |
| 15 | 5b | thiophen-2-yl (6e) | morpholin-1-yl | 7o (90.5) |
a
Reagents and conditions: (a) corresponding boronic acid or ester, K2CO3, PdCl2(PPh3)2, toluene/dioxane/water (10:5:8, v/v/v), 90 °C, overnight; (b) corresponding secondary amine, KI, K2CO3, N,N-diisopropylethylamine, dimethylformamide, 110 °C, overnight.