4-(1H-imidazol-1-yl)-5-iodoPyrimidine synthesis

Yield:1428881-71-3 52.1%

Reaction Conditions:

Stage #1: 1H-imidazolewith sodium hydride in tetrahydrofuran at 20; for 0.25 h;
Stage #2: 4-chloro-5-iodopyrimidine in tetrahydrofuran at 20; for 2 h;

Steps:

60.60A Preparation 60A: 4-(lH-Imidazol-l- l)-5-iodopyrimidine

Preparation 60A: 4-(lH-Imidazol-l- l)-5-iodopyrimidine[00248] To a solution of lH-imidazole (0.085 g, 1.248 mmol) in THF (Volume: 10 mL) was added sodium hydride (0.062 g, 1.560 mmol). After 15 minutes at room temperature, 4-chloro-5-iodopyrimidine (0.25 g, 1.040 mmol) was added as a solution in THF (5 mL). After 2 h at room temperature, the reaction was quenched with water. The reaction mixture was extracted with EtOAc (3X). The combined organics were dried over MgS0₄, filtered and concentrated to give the title compound (0.155 g, 0.541 mmol, 52.1% yield) as a pale yellow solid. ESI MS (M+H)⁺ = 273.0.

References:

WO2013/49263,2013,A1 Location in patent:Paragraph 00247; 00248