反应详情

To a solution of Diethyl-[4-(4-piperazin-1-yl-1H-benzoimidazol-2-yl)-phenyl]-amine (1.0 g, 2.0 mMol) in N-methylpyrrolidinone (10 mL) was added 1-Ethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde (0.404 g, 2.40 mMol) followed by sodium triacetoxyborohydride (0.849 g, 4.01 mMol) and the mixture stirred at room temperature overnight. Upon arrival the crude reaction mixture was diluted with water (2 mL), filtered, and purified by RP-HPLC (Method E) to yield 168 mg (17% yield) of 5-{4-[2-(4-Diethylamino-phenyl)-1H-benzoimidazol-4-yl]-piperazin-1-ylmethyl}-1-ethyl-1H-pyrimidine-2,4-dione as a very light yellow solid. 1H NMR (DMSO-d6): δ=12.33 (s,1H), 11.25 (s,1H), 7.91 (d, 2H, J=9 Hz), 7.66 (s, 1H), 6.96 (m, 2H), 6.77 (d,2H, J=9 Hz), 6.45 (dd, 1H, J=6.0, 2.8 Hz), 3.74 (q, 2H, J=7.1 Hz), 3.53 (br s, 4 h), 3.40 (q, 4H, J=7.1 Hz), 3.23 (s, 2H), 2.62 (m, 4H), 1.18 (t, 3H, J=7.1 Hz), 1.13 (t, 6H, J=7.1 Hz). LC/MS (Method A), rt=0.85 mins., purity=99.2%, calculated mass=501, [M+H]+=502, [M−H]=500. HPLC (Method D): rt=5.5 mins., purity=99.3% @ 210-370 nm and 98.6% @ 372 nm.

1. customUpon arrival the crude reaction mixture
2. filtrationfiltered
3. custompurified by RP-HPLC (Method E)