## 2 Materials and Methods
### Chemistry
Crude material obtained was purified by either silica gel chromatography with a gradient of CH\({}_{2}\)Cl\({}_{2}\): ethyl acetate: solvent system (0-80%) or recrystallized from hot isopropanol or acetonitrile to afford the product. General procedure B for acid catalyzed S\({}_{\text{N}}\)Ar reaction for the preparation of compounds 3, 8a, 10a, 11a. In a sealed vial, desired 4-chloroquinazoline 16-26 (1 equiv.) and 2-[4-(trifluoromethyloormethoxy)phenyl]ethylamine (7, 1 equiv.) were dissolved in a 3:1 tetrahydrofuranran: 2-propanol solution (4 mL). Next, was added 12 M HCl (\(\sim\)0.4 equiv.). The solution was heated at 70 \({}^{\circ}\)C for 24 h. The reaction was concentrated to dryness. The residue was dissolved in CH\({}_{2}\)Cl\({}_{2}\) and washed with saturated aqueous NaHCO\({}_{3}\) solution, water, and brine. The organic phase was collected, dried over sodium sulfate, filtered, and concentrated in vacuo. Crude material obtained was purified by either silica gel column chromatography with a gradient of CH\({}_{2}\)Cl\({}_{2}\): ethyl acetate: solvent system (0-80%) or recrystallized from hot isopropanol or acetonitrile to afford the product. \(N\)-Phenethylquinazolin-4-amine, **3**  
Following general procedure B, using 4-chloroquinazoline (**5**, 100 mg, 0.59 mmol), 2-phenylethylamine (72 mg, 0.59 mmol), and 12 N HCl (11 \(\mu\)L, 0.14 mmol) gave **3** as pale-yellow crystals (43 mg, 28%). mp 171.5-171.9 \({}^{\circ}\)C; \({}^{1}\)H (500 MHz, MeOD) \(\delta\) ppm 8.47 (s, 1H), 8.06 (d, \(J\) = 8.3 Hz, 1H), 7.82-7.77 (m, 1H), 7.72 (d, \(J\) = 8.3 Hz, 1H), 7.55-7.50 (m, 1H), 7.31-7.26 (m, 4H), 7.23-7.17 (m, 1H), 3.86 (t, \(J\) = 7.4 Hz, 2H), 3.04 (t, \(J\) = 7.4 Hz, 2H) \({}^{13}\)C (125 MHz, MeOD) \(\delta\) ppm 160.0, 154.7, 148.2, 139.3, 132.7, 128.5, 128.1, 126.3, 126.0, 125.9, 121.9, 115.1, 42.5, 34.7. HRMS (EI), M + 1 calculated for C\({}_{16}\)H\({}_{15}\)N\({}_{3}\), 250.1339, found 250.1351. These experimental results are consistent with previous reports [14; 15; 16]. Quinazolin-4-yl[2-[4-(trifluoromethylomethyl)phenyl]ethyl]amine, **6a**  
Following general procedure A, using 4-chloroquinazoline (**5**, 100 mg, 0.59 mmol), 2-[4-(trifluoromethylphenyl)phenyl]ethylJamine (114 mg, 0.59 mmol) and potassium carbonate (81 mg, 0.59 mmol) gave **6a** as gold crystals (79 mg, 38%). mp 160.3-161.0 \({}^{\circ}\)C; \({}^{1}\)H (500 MHz, CDCl\({}_{3}\)) \(\delta\) ppm 8.73 (s, 1H), 7.88 (d, \(J\) = 7.9 Hz, 1H), 7.77 (ddd, \(J\) = 8.4, 7.0, 1.3 Hz), 7.63-7.57 (m, 3H), 7.47 (ddd, \(J\) = 8.2, 7.0, 1.2 Hz), 7.40 (d, \(J\) = 8.0 Hz, 2H), 5.79 (br.s, 1H), 3.99 (dt, \(J\) = 6.9, 5.9 Hz, 2H), 3.14 (t, \(J\) = 6.9 Hz, 2H). \({}^{13}\)C (125 MHz, CDCl\({}_{3}\)) \(\delta\) ppm 159.6, 155.4, 149.5, 143.2 (d, \(J\) = 1.5 Hz), 132.7, 129.2, 129.1 (q, \(J\) = 32.4 Hz), 128.2, 126.1, 125.6 (q, \(J\) = 3.8 Hz), 124.7 (q, \(J\) = 271.9 Hz), 120.2, 114.9, 42.1, 35.2. \({}^{19}\)F (470 MHz, CDCl\({}_{3}\)) \(\delta\) ppm \(-\)62.4 (s, 3F). HRMS (EI), M + 1 calculated for C\({}_{17}\)H\({}_{14}\)F\({}_{3}\)N\({}_{3}\), 318.1213, found 318.1229. This compound appears in referenced patent and fungicidal activity was reported [17]. Quinazolin-4-yl[2-[4-(trifluoromethylomethyl)phenyl]ethyl]amine, **7a**  
Following general procedure A, using 4-chloroquinazoline (**5**, 100 mg, 0.59 mmol), 2-[4-(trifluoromethylomethyl)phenyl]ethylJamine (125 mg, 0.59 mmol) and potassium carbonate (84 mg, 0.59 mmol) gave **7a** as white crystals (85 mg, 42%). mp 137.4-137.8 \({}^{\circ}\)C; \({}^{1}\)H (500 MHz, CDCl\({}_{3}\)) \(\delta\) ppm 8.73 (s, 1H), 7.88 (d, \(J\) = 8.2 Hz, 1H), 7.77 (ddd, \(J\) = 8.4, 7.0, 1.3 Hz, 1H), 7.60-7.56 (m, 1H), 7.48 (ddd, \(J\) = 8.3, 7.0, 1.1 Hz), 7.33-7.26 (m, 2H), 7.20 (d, \(J\) = 8.0 Hz, 2H), 5.73 (br.s, 1H), 3.97 (dt, \(J\) = 7.0, 5.9 Hz, 2H), 3.08 (t, \(J\) = 7.0 Hz, 2H). \({}^{13}\)C (125 MHz, CDCl\({}_{3}\)) \(\delta\) ppm 159.3, 155.4, 149.5, 148.0 (d, \(J\) = 1.8 Hz), 137.7, 132.6, 130.2, 128.8, 126.1, 121.3, 120.6 (q, \(J\) = 235.0 Hz), 120.1, 114.9, 42.3, 34.6.