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

HRID 617288Notes

Reaction equation

[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[CH2:7][OH:8].[H-].[Na+].[Cl:11][C:12]1[N:13]=[N:14][C:15](Cl)=[CH:16][CH:17]=1>C1COCC1>[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[CH2:7][O:8][N:14]1[CH:15]=[CH:16][CH:17]=[C:12]([Cl:11])[NH:13]1

Participants

Conditions

Temperature: 0 °C

Procedure

(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).

Workup

temperaturethe mixture was slowly warmed to room temperature
stirringwith stirring
stirringThe reaction was stirred for 48 hours
customThe solvent was then evaporated in vacuo
additionthe mixture diluted with chloroform
washwashed with saturated NaHCO3
dry with materialThe organic layer was dried over MgSO4
customThe resulting crude material was purified by flash chromatography (10% MeOH/CHCl3)

Sources & evidence

ORD record: ord-9052d1061d8c44f59961c576cde9c6c2
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05948793

Reaction notes

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