## 3 Materials and Methods
### Analytics of the Synthesized Compounds  
_2-chloro-4-phenylpyrimidine (3):_ white solid, Mp 86-87 \({}^{\circ}\)C (lit. 84-86 \({}^{\circ}\)C [41]); \({}^{1}\)H NMR (400 MHz, CDCl\({}_{3}\)): \(\delta\) (ppm) = 7.48-7.54 (m, 3H), 7.64 (d, \(J\) = 5.3 Hz, 1H), 8.07-8.10 (m, 2H), 8.63 (d, \(J\) = 5.3 Hz, 1H); \({}^{13}\)C NMR (100 MHz, CDCl\({}_{3}\)): \(\delta\) (ppm) = 115.27, 127.55, 129.25, 132.04, 135.17, 159.95, 161.99, 167.30; HRMS (ESI+) \(m/z\) calc. for C\({}_{10}\)H\({}_{8}\)N\({}_{2}\)Cl [M + H]\({}^{+}\) 191.0371, found 191.0369; HPLC \(t_{\rm B}\) = 6.41 min; Rf = 0.43 (EtOAc/n-Hex, 1:2, \(v/v\)). 4-chloro-2-phenylpyrimidine (4): white solid, Mp 72-73 \({}^{\circ}\)C (lit. 73-74 \({}^{\circ}\)C [42]); \({}^{1}\)H NMR (400 MHz, CDCl\({}_{3}\)): \(\delta\) (ppm) = 7.23 (d, \(J\) = 5.2 Hz, 1H), 7.48-7.52 (m, 3H), 8.43-8.46 (m, 2H), 8.67 (d, \(J\) = 5.2 Hz, 1H); \({}^{13}\)C NMR (100 MHz, CDCl\({}_{3}\)): \(\delta\) (ppm) = 119.45, 128.66, 128.81, 131.68, 136.23, 158.39, 161.70, 165.71; HRMS (ESI+) \(m/z\) calc. for C\({}_{10}\)H\({}_{8}\)N\({}_{2}\)Cl [M + H]\({}^{+}\) 191.0371, found 191.0371, HPLC \(t_{R}\) = 7.09 min; Rf = 0.55 (EtOAc/n-Hex, 1:2, _v/v_). 2-chloro-4-(2-methoxyphenyl)pyrimidine (26): Yield: 76%; white solid; Mp 53-54 \({}^{\circ}\)C; \({}^{1}\)H NMR (400 MHz, CDCl\({}_{3}\)): \(\delta\) (ppm) = 3.92 (s, 3H), 7.00-74 (m, 1H), 7.11 (td, \(J_{1}\) = 1.1 Hz, J2 = 7.6 Hz, 1H), 7.48 (ddd, J1 = 1.8 Hz, J2 = 7.4 Hz, J3 = 8.4 Hz, 1H), 7.97 (d, \(J\) = 5.3 Hz, 1H), 8.09 (dd, \(J_{1}\) = 1.8 Hz, J2 = 7.8 Hz, 1H), 8.57 (d, \(J\) = 5.3 Hz, 1H) as reported [43]; \({}^{13}\)C NMR (100 MHz, CDCl\({}_{3}\)): \(\delta\) (ppm) = 55.76, 111.65, 120.21, 121.43, 124.53, 131.47, 13.86, 158.32, 159.05, 161.31, 165.82; HRMS (ESI+) \(m/z\) calc. for C\({}_{10}\)H\({}_{10}\)N\({}_{2}\)OCI [M + H]\({}^{+}\) 221.0476, found 221.0476; HPLC \(t_{R}\) = 6.41 min; Rf = 0.36 (EtOAc/n-Hex, 1:4, _v/v_). 2-chloro-4-(3-methoxyphenyl)pyrimidine (27): Yield: 72%; white solid; Mp 68-70 \({}^{\circ}\)C (lit. 83-86 \({}^{\circ}\)C [44]); \({}^{1}\)H NMR (400 MHz, CDCl\({}_{3}\)): \(\delta\) (ppm) = 3.90 (s, 3H), 7.09 (ddd, \(J_{1}\) = 0.9 Hz, \(J_{2}\) = 2.6 Hz, \(J_{3}\) = 8.2 Hz, 1H), 7.42 (t, \(J\) = 8.0 Hz, 1H), 7.63 (d, \(J\) = 5.3 Hz, 1H), 7.61-7.67 (m, 2H), 8.64 (d, \(J\) = 5.3 Hz, 1H); \({}^{13}\)C NMR (100 MHz, CDCl\({}_{3}\)): \(\delta\) (ppm) = 55.67, 112.61, 115.48, 118.06, 119.92, 130.29, 136.64, 159.97, 160.41, 161.99, 167.17; HRMS (ESI+) \(m/z\) calc. for C\({}_{10}\)H\({}_{10}\)N\({}_{2}\)OCl [M + H]\({}^{+}\) 221.0476, found 221.0476; HPLC \(t_{R}\) = 6.34 min; Rf = 0.24 (EtOAc/n-Hex, 1:4, _v/v_). 2-chloro-4-(4-methoxyphenyl)pyrimidine (28): Yield: 77%; white solid; Mp 106-108 \({}^{\circ}\)C (lit. 137-140 \({}^{\circ}\)C [44]); \({}^{1}\)H NMR (400 MHz, CDCl\({}_{3}\)): \(\delta\) (ppm) = 3.89 (s, 3H), 6.99-7.03 (m, 2H), 7.57 (d, \(J\) = 5.3 Hz, 1H), 8.06-8.10 (m, 2H), 8.56 (d, \(J\) = 5.3 Hz, 1H); \({}^{13}\)C NMR (100 MHz, CDCl\({}_{3}\)): \(\delta\) (ppm) = 55.65, 114.32, 114.63, 127.57, 129.30, 159.58, 161.90, 162.96, 166.79; HRMS (ESI+) \(m/z\) calc. for C\({}_{11}\)H\({}_{10}\)N\({}_{2}\)Cl [M + H]\({}^{+}\) 221.0476, found 221.0476; HPLC \(t_{R}\) = 6.30 min; Rf = 0.18 (EtOAc/n-Hex, 1:4, _v/v_). 2-chloro-4-(m-tolyl)pyrimidine (29): Yield: 75%; white solid; Mp 74-75 \({}^{\circ}\)C; \({}^{1}\)H NMR (400 MHz, CDCl\({}_{3}\)): \(\delta\) (ppm) = 2.45 (s, 3H), 7.34-7.38 (m, 1H), 7.40 (t, \(J\) = 7.5 Hz, 1H), 7.64 (d, \(J\) = 5.3 Hz, 1H), 7.84-7.87 (m, 1H), 7.92-7.94 (m, 1H), 8.62 (d, \(J\) = 5.3 Hz, 1H); \({}^{13}\)C NMR (100 MHz, CDCl\({}_{3}\)): \(\delta\) (ppm) = 21.59, 115.38, 124.72, 128.18, 129.16, 132.87, 135.18, 139.16, 159.88, 161.98, 167.56; HRMS (ESI+) \(m/z\) calc. for C\({}_{11}\)H\({}_{10}\)N\({}_{2}\)Cl [M + H]\({}^{+}\) 205.0527, found 205.0529; HPLC \(t_{R}\) = 6.87 min; Rf = 0.35 (EtOAc/n-Hex, 1:3, _v/v_).