Sodium hydride → 2-((1-methyl-2-(R)-pyrrolidinyl)methoxy)-6-chloropyridazine

Participants

Reaction Conditions

Reaction Steps

(R)-1-Methyl-2-pyrrolidinemethanol (300 mg, 2.61 mmol) was dissolved in anhydrous THF and cooled to 0° C. with stirring. NaH (80% dispersion in mineral oil, 0.082 g, 2.9 mmol) was added and the mixture was slowly warmed to room temperature with stirring. After 30 minutes a THF solution of 3,6-dichloropyridazine (0.41 g, 2.74 mmol) was added to the mixture via syringe. The reaction was stirred for 48 hours. The solvent was then evaporated in vacuo and the mixture diluted with chloroform, washed with saturated NaHCO3 and then with brine. The organic layer was dried over MgSO4. The resulting crude material was purified by flash chromatography (10% MeOH/CHCl3) to give 0.25 g (42% yield) of the title compound as a cream colored solid. MS (DCI/NH3) m/e 228 (M+H)+. [α]25D =+32° (c=1, MeOH).

Provenance & Evidence