Diisopropylethylamine → HCID 59239551, compound

Participants

Reaction Steps

To a suspension of (S)-1-ethyl-3-(4-(4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (301 mg, 0.759 mmol) in Acetonitrile (1.3 mL), N-Methylpyrrolidinone (0.44 mL) and N,N-Diisopropylethylamine (0.40 mL, 2.3 mmol) was added (2-Bromoethoxy)-tert-butyldimethylsilane (0.82 mL, 3.8 mmol), and the reaction was kept at 50° C. overnight. LC-MS showed the reaction was completed (desired peak m/z=555 (M+H)). The yellow solution was evaporated to dryness as much as possible, followed by dilution in Methylene chloride (6.0 mL) and Methanol (3.0 mL). Then, 4.0 M of Hydrogen chloride in 1,4-Dioxane (5.7 mL) was added, and the yellow solution was stirred at room temperature for 2.5 h. The solvents were removed and the residue was purified to give the final product ry (174.4 mg, 52% yield after two steps) as off-white powder: 1H NMR (400 MHz, DMSO) δ 8.65 (s, 1H), 8.15 (d, J=8.8 Hz, 2H), 7.47 (d, J=8.7 Hz, 2H), 6.18 (t, J=5.5 Hz, 1H), 4.48 (m, 1H), 4.12 (m, 1H), 3.87 (d, J=10.6 Hz, 1H), 3.75-3.48 (m, 8H), 3.40 (t, J=11.3 Hz, 1H), 3.17-3.04 (m, 2H), 2.80-2.53 (m, 6H), 1.22 (d, J=6.6 Hz, 3H), 1.06 (t, J=7.2 Hz, 3H); LC-MS m/z=441 (M+H).

Provenance & Evidence