HCID 59924696, compound → HCID 59924927, compound

Participants

Reaction Steps

To a solution of methylmagnesium bromide (980 μL, 1.4 M, 13.8 mmol) in CH2Cl2 (0.5 mL) at 0° C. was added 2-[(S)-1-phenylethylamino]-4-[5-(N-methyl-N-methoxyaminocarbonyl)-benzimidazol-1-yl]pyrimidine (55.4 mg, 0.138 mmol) in CH2Cl2 (1.0 mL) slowly. The reaction mixture was warmed to room temperature slowly and continued stirring for 5 h. The reaction mixture was quenched with saturated aqueous NH4Cl then extracted with CH2Cl2. The combined extracts were washed with brine and dried over Na2SO4. The crude material was purified by preparative thin layer chromatography eluting with 3% MeOH/CH2Cl2 to obtain 38 mg of the title compound. Partial 1H NMR (500 MHz, CDCl3): δ 8.5 (br s, 1H); 8.4 (s, 1H); 8.38 (d, J=5.5 Hz, 1H); 7.93 (br s, 1H); 7.79 (br s, 1H); 7.44-7.28 (m, 5H); 6.74 (d, J=5.2 Hz, 1H); 5.17 (br s, 1H); 2.68 (s, 3H); 1.63 (d, J=6.8 Hz, 3H). Mass spectrum 358.2 (CI, M+1).

Provenance & Evidence