Dimethylformamide → HCID 123485213, compound

Participants

Reaction Steps

To a solution of tert-butyl(1-(4-(2-oxo-7-phenyl-1,2,3,4-tetrahydropyrido[3,2-d]pyrimidin-6-yl)phenyl)cyclobutyl)carbamate (46 mg, 0.10 mmol) in dry DMF (1 ml) at −78 C was added sodium hydride (3.9 mg, 0.10 mmol) and methyliodide (6.1 μl, 0.10 mmol) under nitrogen. The bath was removed and the resulting mixture was stirred for 1 h at room temperature. The mixture was cooled down to −78 C. Sodium hydride (3.9 mg, 0.10 mmol) and methyliodide (6.10, μl, 0.10 mmol) were added under nitrogen. The bath was removed and the resulting mixture was stirred for 1 h at room temperature. Water was added and the mixture was extracted with EtOAc (3×10 ml). The combined organic phases were dried over Na2SO4 and concentrated to dryness under reduced pressure. The resulting residue was purified by Biotage silica gel chromatography (gradient 0 to 50% EtOAc in cyclohexane) to give the title compound (30 mg, 61%). 1H NMR (500 MHz, CDCl3): 7.20-7.19 (7H, m), 7.13-7.11 (2H, m), 7.02 (1H, s), 5.00 (1H, br s), 4.56 (2H, s), 3.27 (3H, s), 3.03 (3H, s), 2.52-2.20 (4H, m), 2.00-1.95 (1H, m), 1.79-1.65 (1H, m), 1.40-1.10 (9H, br)

Provenance & Evidence