Acetic Acid → HCID 11704483, compound

Participants

Reaction Steps

5-(3-Hydroxypropoxy)-N-methylpyridine-2-carboxamide (52 mg, 0.25 mmol) in N,N-dimethylacetamide (2.0 mL, 22 mmol) was treated with sodium hydride (11 mg, 60%, 0.27 mmol) at ambient temperature. After 1.5 hours, the mixture was added to a solution of 4-chloro-5-pyridin-4-ylthieno[2,3-d]pyrimidine (62 mg, 0.025 mmol) in N,N-dimethylacetamide (1.0 mL) and the resulting mixture was stirred at room temperature for 12 hours. The reaction mixture was then quenched by the addition of acetic acid (0.12 mL, 2.0 mmol) and the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (50 mL), washed with 5% aqueous sodium bicarbonate (2×30 mL) and the organic layer was concentrated. The product was purified by silica gel chromatography using 3 to 5% methanol in ethyl acetate to give 72 mg (68%) of N-methyl-5-{3-[(5-pyridin-4-ylthieno[2,3-d]pyrimidin-4-yl)oxy]propoxy}pyridine-2-carboxamide as a white solid. MS [M+H] 422.0, 1H NMR (CDCl3) δ (ppm) 8.74 (s, 1H), 8.66 (s, 1H), 8.54 (d, J=3.9 Hz, 1H), 8.11 (d, J=8.4 Hz, 1H), 8.05 (d, J=2.7 Hz, 1H), 7.90-7.73 (m, 2H), 7.33 (s, 1H), 7.28 (dd, J=7.8, 4.8 Hz, 1H), 7.11 (dd, J=8.7, 2.7 Hz, 1H), 4.62 (t, J=6.0 Hz, 2H), 3.76 (t, J=6.0 Hz, 2H), 3.01 (d, J=4.8 Hz, 3H), 2.13 (t, J=6.0 Hz, 2H).

Provenance & Evidence