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

HRID 709734Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 4,6-dichloro-5-methylpyrimidine (160 mg) and (6-(2,2-dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methanol (300 mg) in THF (8.0 mL) was added 60% sodium hydride (60 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 (340 mg) 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-d68757376dbb416fbcd8bfd7b2b4f4f4
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181186B2

Reaction notes

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