Hydrochloric Acid → 4-Chloro-6-((6-(2,2-dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methoxy)-5-methoxypyrimidine

HRID 709738

Reaction equation

Cl[C:2]1[C:7]([O:8][CH3:9])=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=1.[CH3:11][C:12]([CH3:32])([CH3:31])[CH2:13][C:14]1[N:19]=[C:18]([CH2:20][OH:21])[CH:17]=[CH:16][C:15]=1[C:22]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=1[F:30].[H-].[Na+].Cl>C1COCC1>[Cl:10][C:6]1[C:7]([O:8][CH3:9])=[C:2]([O:21][CH2:20][C:18]2[CH:17]=[CH:16][C:15]([C:22]3[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=3[F:30])=[C:14]([CH2:13][C:12]([CH3:32])([CH3:31])[CH3:11])[N:19]=2)[N:3]=[CH:4][N:5]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 4,6-dichloro-5-methoxypyrimidine (450 mg) and (6-(2,2-dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methanol (760 mg) in THF (8.0 mL) was added 60% sodium hydride (200 mg) at 0° C., and the mixture was stirred at 50° C. for 2 hr. The reaction mixture was neutralized with 1N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.05 g) as a white solid.

Workup

extractionextracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-509e63ab996b4640a72d67164b916ff6
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181186B2

Linked notes

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