Water → 6-Tert-butyl-2-[4-[5-[(1,5-dimethylpyrazol-3-yl)amino]-1-methyl-6-oxo-pyridazin-3-yl]-3-(hydroxymethyl)-2-pyridyl]-8-fluoro-phthalazin-1-one

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Lithium Hydroxide	HCID 3939	—
Reactant	(2-(6-tert-Butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-(5-(1,5-dimethyl-1H-pyrazol-3-ylamino)-1-methyl-6-oxo-1,6-dihydropyridazin-3-yl)pyridin-3-yl)methyl Acetate	HCID 86683974	—
Solvent	Isopropanol	HCID 3776	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	6-Tert-butyl-2-[4-[5-[(1,5-dimethylpyrazol-3-yl)amino]-1-methyl-6-oxo-pyridazin-3-yl]-3-(hydroxymethyl)-2-pyridyl]-8-fluoro-phthalazin-1-one	HCID 86683975	18.4%

Reaction Conditions

Temperature	30 °C

Reaction Steps

To a solution of 127c (176 mg, 0.30 mmol) in propan-2-ol (4 mL), tetrahydrofuran (4 mL), and water (1.0 mL) was added lithium hydroxide (72 mg, 3.0 mmol). The mixture was stirred at 30° C. for 2 h. It was then evaporated under reduced pressure and the residue was purified by reverse-phase prep-HPLC to afford 127 (30 mg, 18%) as a white solid. MS-ESI: [M+H]+ 544.8. 1H NMR (500 MHz, MeOD) δ 8.66 (d, J=5.0 Hz, 1H), 8.51 (d, J=2.5 Hz, 1H), 7.88 (s, 1H), 7.88 (s, 1H), 7.76-7.72 (m, 2H), 5.97 (s, 1H), 4.68 (s, 2H), 3.89 (s, 3H), 3.75 (s, 3H), 2.29 (s, 3H), 1.47 (s, 9H)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08669251B2
Source dataset	uspto-grants-2014_03
ORD ID	ord-b25a37782a1d4cb2889c9c393c0c47eb
Source note	uspto-grants-2014_03