Sodium Hydroxide → 3-cyclopentyl-2-[4-(4,6-dimethyl-pyrimidin-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 3-cyclopentyl-2-[4-(4,6-dimethyl-pyrimidin-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid methyl ester (206 mg, 0.55 mmol) in tetrahydrofuran (4 mL) was treated with a 4N aqueous sodium hydroxide solution (0.17 mL) and was stirred at 25° C. for 4 h. The reaction was partitioned between water (3 mL) and ether. The aqueous layer was back extracted with ether. The aqueous layer was then acidified to pH 3-4 with a 1N aqueous hydrochloric acid solution. The resulting precipitate was filtered, rinsed with water (1 mL), and dried in vacuo to afford 3-cyclopentyl-2-[4-(4,6-dimethyl-pyrimidin-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid as a white solid (40 mg, 20%); LC-MS: tR=3.71 min, 359 [M+H]+. HPLC: tR=7.02 min, 96.21% at 214 nm, 98.34% at 254 nm. 1H NMR (300 MHz, DMSO-d6): δ13.03 (broad, 1H), 8.12 (d, 1H, J=2.7 Hz), 7.19 (s, 1H), 6.85 (d, 1H, J=2.4 Hz), 5.36 (dd, 1H, J=10.5 Hz, J=4.2 Hz), 2.41 (s, 6H), 2.24-2.14 (m, 1H), 2.05-1.97 (m, 1H), 1.71-1.44 (m, 7H), 1.17-1.04 (m, 2H).

Provenance & Evidence