||Stage #1: 4-(1,3-oxazol-2-yl)aniline With trimethylaluminum In toluene at 0℃; for 0.5h;
Stage #2: ethyl 2,4-dimethylimidazo[1,5-a]pyrimidine-8-carboxylate In toluene at 0 - 100℃; for 14.1667h;
||8 EXAMPLE 8- PREPARATION OF 2,4-DIMETHYL-N-(4-(OXAZOL-2-YL)PHENYL)IMIDAZO[1,5- a]PYRIMIDINE-8-CARBOXAMIDE
EXAMPLE 8- PREPARATION OF 2,4-DIMETHYL-N-(4-(OXAZOL-2-YL)PHENYL)IMIDAZO[1,5- a]PYRIMIDINE-8-CARBOXAMIDE A solution of 4-(oxazol-2-yl)aniline (80 mg, 0.54 mmol) in toluene (4 mL) at 0C was charged with 2M solution of trimethyl aluminum in toluene (0.9 mL, 1.60 mmol) and stirred at 0C for 30 min. To the resulting mixture was added a solution of ethyl 2,4- dimethylimidazo[1,5-a]pyrimidine-8-carboxylate 2 (100 mg, 0.45 mmol) in toluene (1 mL) and stirred for 10 min. Then, the reaction mixture was heated to 100C for 14 h. Next, the reaction mixture was quenched with 1N HCl and extracted with DCM (2 x 10 mL) to obtain crude compound. The crude compound was purified by FCC (eluent, 1% methanol in DCM) to afford the title compound as a yellow solid (25 mg, 16%).1H NMR (400 MHz, DMSO-d6) δ 10.04 (s, 1H), 8.04 (d, J=8.9 Hz, 2H), 8.00 (d, J=8.8 Hz, 1H), 7.90 (d, J=8.9 Hz, 2H), 7.69 (s, 1H), 7.22 (d, J=8.8 Hz, 1H), 6.56 (s, 1H), 2.68 (s, 6H). ES-MS m/z 333.35 (M+H)+. HPLC purity 92.5%.