## 3 Materials and Methods
### Analytics of the Synthesized Compounds
_2-chloro-4-(napthtalen-2-yl)pyrimidine (37)_: Yield: 87%; white solid; Mp 114-116 \({}^{\circ}\)C; \({}^{1}\)H NMR NMR (400 MHz, CDCl\({}_{3}\)): 8 (ppm) = 7.54-7.62 (m, 2H), 7.79 (d, \(J\) = 5.3 Hz, 1H), 7.88-7.92 (m, 1H), 7.95-8.01 (m, 2H), 8.15 (dd, \(J_{1}\) = 1.9 Hz, \(J_{2}\) = 8.6 Hz, 1H), 8.65-8.67 (m, 1H), 8.68 (d, \(J\) = 5.3 Hz, 1H); \({}^{13}\)C NMR (100 MHz, CDCl\({}_{3}\)): 8 (ppm) = 115.49, 123.78, 127.08, 127.95, 128.19, 128.40, 129.17, 129.38, 132.42, 133.26, 135.17, 160.01, 162.10, 167.27; HRMS (ESI+) \(m\)/\(\varepsilon\) calc. for C\({}_{14}\)H\({}_{10}\)N\({}_{2}\)Cl [M + H]\({}^{+}\) 241.0527, found 241.0528 as reported [50]; HPLC \(t_{R}\) = 7.31 min; Rf = 0.28 (EtOAc/n-Hex, 1:3, \(v\)/\(v\)). _2-chloro-4-(furan-2-yl)pyrimidine (38)_: Yield: 50%; white solid; Mp 67-69 \({}^{\circ}\)C; \({}^{1}\)H NMR (400 MHz, CDCl\({}_{3}\)): 8 (ppm) = 6.61 (dd, \(J_{1}\) = 1.7 Hz, \(J_{2}\) = 3.5 Hz, 1H), 7.39 (dd, \(J_{1}\) = 0.7 Hz, \(J_{2}\) = 3.5 Hz, 1H), 7.53 (d, \(J\) = 5.2 Hz, 1H), 7.63 (dd, \(J_{1}\) = 0.7 Hz, \(J_{2}\) = 1.7 Hz, 1H), 8.58 (d, \(J\) = 5.2 Hz, 1H) as reported [51]; \({}^{13}\)C NMR (100 MHz, CDCl\({}_{3}\)): 8 (ppm) = 113.10, 113.13, 114.58, 146.24, 150.52, 158.11, 159.92, 161.76; HRMS (ESI+) \(m\)/\(\varepsilon\) calc. for C\({}_{8}\)H\({}_{6}\)ON\({}_{2}\)Cl [M + H]\({}^{+}\) 181.0163, found 181.01613, f _2-chloro-6-phenylpyrimidine-4-carboxylic acid (42)_: Yield: 92%; appearance; Mp \(>\) 300 \({}^{\circ}\)C; \({}^{1}\)H NMR (400 MHz, DMSO\({}_{d}\)\({}_{6}\)): \(\delta\) (ppm) = 7.51-7.58 (m, 3H), 8.13-8.16 (m, 2H), 8.29 (s, 1H), 1H from COOH is exchanged; \({}^{13}\)C NMR (100 MHz, DMSO\({}_{d}\)\({}_{6}\)): \(\delta\) (ppm) = 114.06, 127.24, 129.17, 131.80, 134.90, 160.30, 165.40, 166.62, 168.53; HRMS (ESI-) \(m\)/\(z\) calc. for C\({}_{11}\)H\({}_{0}\)O\({}_{2}\)N\({}_{2}\)C1 [M \(-\) H ] - 233.0123, found 233.0121; HPLC \(t_{R}\) = 5.29 min; Rf = 0.04 (DCM/MeOH; 9:1, _v/v_) _2-chloro-4-methyl-6-phenylpyrimidine (43)_: Yield: 78%; pale orange solid; Mp 42-44 \({}^{\circ}\)C; \({}^{1}\)H NMR (400 MHz, CDCl\({}_{3}\)): \(\delta\) (ppm) = 2.60 (s, 3H), 7.48-7.55 (m, 4H), 8.06-8.08 (m, 2H) as reported [53]; \({}^{13}\)C NMR (100 MHz, CDCl\({}_{3}\)): \(\delta\) (ppm) = 24.37, 100.13, 114.87, 127.55, 129.19, 131.75, 135.49, 166.96, 170.98; HRMS (ESI+) \(m\)/\(z\) calc. for C\({}_{11}\)H\({}_{10}\)N\({}_{2}\)Cl [M + H]\({}^{+}\) 205.0527, found 205.0528; HPLC \(t_{R}\) = 6.60 min; Rf = 0.41 (EtOAc/n-Hex, 1:2, _v/v_). _2-chloro-4-methoxy-6-phenylpyrimidine (44A)_: Yield: 34%; white solid; Mp 88-90 \({}^{\circ}\)C; \({}^{1}\)H NMR (400 MHz, CDCl\({}_{3}\)): \(\delta\) (ppm) = 4.05 (s, 3H), 7.03 (s, 1H), 7.47-7.51 (m, 3H), 8.00-8.03 (m, 2H); \({}^{13}\)C NMR (100 MHz, CDCl\({}_{3}\)): \(\delta\) (ppm) = 54.87, 102.05, 127.36, 129.06, 131.38, 135.62, 160.45, 167.10, 171.87; HRMS (ESI+) \(m\)/\(z\) calc. for C\({}_{11}\)H\({}_{10}\)ON\({}_{2}\)Cl [M + H]\({}^{+}\) 221.0476, found 221.0477; HPLC \(t_{R}\) = 7.41 min; Rf = 0.62 (EtOAc/n-Hex, 1:2, _v/v_). _4-chloro-6-methoxy-2-phenylpyrimidine (44B)_: Yield: 36%; white solid; Mp 49-51 \({}^{\circ}\)C; \({}^{1}\)H NMR (400 MHz, CDCl\({}_{3}\)): \(\delta\) (ppm) = 4.11 (s, 3H), 6.66 (s, 1H), 7.47-7.54 (m, 3H), 8.42-8.46 (m, 2H); \({}^{13}\)C NMR (100 MHz, CDCl\({}_{3}\)): \(\delta\) (ppm) = 54.44, 105.24, 128.62, 128.67, 131.59, 136.35, 161.10, 164.79, 170.77; HRMS (ESI+) \(m\)/\(z\) calc. for C\({}_{11}\)H\({}_{10}\)ON\({}_{2}\)Cl [M + H]\({}^{+}\) 221.0476, found 221.0475; HPLC \(t_{R}\) = 7.96 min; Rf = 0.65 (EtOAc/n-Hex, 1:2, _v/v_). _2-chloro-6-phenylpyrimidine-4-amine (45)_: Yield: 84%; pale yellow solid; Mp 160-162 \({}^{\circ}\)C; \({}^{1}\)H NMR (400 MHz, CDCl3): \(\delta\) (ppm) = 5.39 (s, 2H), 6.72 (s, 1H), 7.44-7.48 (m, 3H), 7.94-7.96 (m, 2H); \({}^{13}\)C NMR (100 MHz, CDCl\({}_{3}\)): \(\delta\) (ppm) = 98.87, 127.20, 128.94, 131.05, 136.12, 161.13, 165.10, 166.03; HRMS (ESI+) \(m\)/\(z\) calc.