Dimethylformamide → HCID 86683644, 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 (71 mg, 0.15 mmol) in dry DMF (1 ml) was added potassium carbonate (21 mg, 0.15 mmol) and methyl iodide (9.4 μl, 0.15 mmol) under nitrogen. The resulting mixture was stirred overnight at room temperature. Potassium carbonate (42 mg, 0.30 mmol) and methyl iodide (18.8 μl, 0.30 mmol) were added under nitrogen. The resulting mixture was stirred for 1 hr at room temperature. Potassium carbonate (146 mg, 1.05 mmol) and methyl iodide (66 μl, 1.05 mmol) were added under nitrogen. The resulting mixture was stirred for 4 hr at 60° C. Saturated sodium bicarbonate solution was added and the mixture was extracted with ethyl acetate (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 100% EtOAc in cyclohexane) to give the title compound (31 mg, 42%). LCMS (Method D): RT=1.437 min, M+H+=485. 1H NMR (500 MHz, CDCl3): 7.25-7.38 (7H, m), 7.20-7.25 (2H, m), 7.16 (1H, s), 5.47 (1H, br s), 5.10 (1H, br s), 4.73 (2H, s), 3.35 (3H, s), 2.25-2.70 (4H, br m), 2.00-2.13 (1H, m), 1.75-1.85 (1H, m), 1.10-1.40 (9H, br).

Provenance & Evidence