| 43% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 100℃; for 2h; Inert atmosphere; |
A.4.8 2,7-dichloro-4-(3-(methoxymethoxy)phenyl)pyrido[3,2-d]pyrimidine
Under an inert atmosphere, in a 25 mL flask, 200 mg (0.85 mmol, 1.0 equiv.) of ( 3) were dissolved in toluene (10 mL). 145 mg (0.90 mmol, 1.05 equiv.) of 3-methoxymethoxyphenylboronic acid, an aqueous solution (1 mL) containing 176 mg (1.28 mmol, 1.5 equiv.) of potassium carbonate, and then 49 mg (0.05 mmol, 0.05 equiv.) of tetrakis triphenylphosphine were added to the medium. The mixture was then brought to 100° C. for 2 hours. After concentration under reduced pressure, the residue was taken up in dichloromethane (30 mL). The organic phase was washed with water (2×10 mL), dried on MgSO4, filtered and then concentrated under reduced pressure. The crude residue was then directly purified by chromatography on silica gel with (DCM/MeOH, 99/1) mixture in order to obtain the product as a yellow solid with a yield of 43%. MP: 214° C. Infrared (Diamand ATR, cm-1) ν: 2972, 1592, 1556, 1492, 1460, 1381, 1335, 1242, 1142, 746; 1H NMR (400 MHz, CDCl3) δ: 3.82 (s, 3H, CH3), 5.30 (s, 2H, CH2), 6.96 (s, 1H, Harom), 7.35 (d, 1H, J=5.5 Hz, Harom), 7.94 (s, 2H, 2×Harom), 8.48 (d, 1H, J=3.2 Hz, H8), 8.92 (d, 1H, J=3.4 Hz, H6); 13C NMR (101 MHz, CDCl3) δ: 56.3 (CH3), 94.5 (CH2), 115.0 (CH), 118.5 (CH), 119.3 (CH), 129.7 (CH), 134.0 (CH), 138.0 (Cq), 142.1 (Cq), 149.1 (CH), 157.6 (Cq), 160.5 (Cq), 162.9 (Cq), 163.8 (Cq), 165.6 (Cq); HRMS (EI-MS): C18H11Cl2N3O2 [M+H]+, calculated m/z 337.0228. found m/z 337.0316 |
| 43% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 100℃; for 2h; Inert atmosphere; |
A.8 2,7-dichloro-4-(3-(methoxymethoxy)phenyl)pyrido[3,2-d]pyrimidine (49)
Under an inert atmosphere, in a 25 mL flask, 200 mg (0.85 mmol, 1.0 equiv.) of (8 3) were dissolved in 188 toluene (10 mL). 145 mg (0.90 mmol, 1.05 equiv.) of 3-methoxymethoxyphenylboronic acid, an aqueous solution (1 mL) containing 176 mg (1.28 mmol, 1.5 equiv.) of 32 potassium carbonate, and then 49 mg (0.05 mmol, 0.05 equiv.) of 189 tetrakis triphenylphosphine were added to the medium. The mixture was then brought to 100° C. for 2 hours. After concentration under reduced pressure, the residue was taken up in dichloromethane (30 mL). The organic phase was washed with water (2×10 mL), dried on MgSO4, filtered and then concentrated under reduced pressure. The crude residue was then directly purified by chromatography on silica gel with (DCM/MeOH, 99/1) mixture in order to obtain the 190 product as a yellow solid with a yield of 43%. MP: 214° C. Infrared (Diamand ATR, cm-1) ν: 2972, 1592, 1556, 1492, 1460, 1381, 1335, 1242, 1142, 746; 1H NMR (400 MHz, CDCl3) δ: 3.82 (s, 3H, CH3), 5.30 (s, 2H, CH2), 6.96 (s, 1H, Harom), 7.35 (d, 1H, J=5.5 Hz, Harom), 7.94 (s, 2H, 2×Harom), 8.48 (d, 1H, J=3.2 Hz, H8), 8.92 (d, 1H, J=3.4 Hz, H6); 13C NMR (101 MHz, CDCl3) δ: 56.3 (CH3), 94.5 (CH2), 115.0 (CH), 118.5 (CH), 119.3 (CH), 129.7 (CH), 134.0 (CH), 138.0 (Cq), 142.1 (Cq), 149.1 (CH), 157.6 (Cq), 160.5 (Cq), 162.9 (Cq), 163.8 (Cq), 165.6 (Cq); HRMS (EI-MS): C18H11Cl2N3O2 [M+H]+, calculated m/z 337.0228. found m/z 337.0316. |
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