Hydrochloric Acid → HCID 131733908, compound

HRID 709729Notes

Reaction equation

[CH3:1][C:2]([CH3:22])([CH3:21])[CH2:3][C:4]1[N:9]=[C:8]([CH2:10][OH:11])[CH:7]=[CH:6][C:5]=1[C:12]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=1[F:20].Cl[C:24]1[N:29]=[C:28]([CH3:30])[N:27]=[C:26]([CH:31]=[CH:32][C:33]([O:35]C)=[O:34])[CH:25]=1.[H-].[Na+].Cl>C1COCC1>[CH3:1][C:2]([CH3:22])([CH3:21])[CH2:3][C:4]1[N:9]=[C:8]([CH2:10][O:11][C:24]2[N:29]=[C:28]([CH3:30])[N:27]=[C:26]([CH:31]=[CH:32][C:33]([OH:35])=[O:34])[CH:25]=2)[CH:7]=[CH:6][C:5]=1[C:12]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=1[F:20]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (6-(2,2-dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methanol (606 mg) and methyl 3-(6-chloro-2-methylpyrimidin-4-yl)acrylate (424 mg) in THF (10 mL) was added 60% sodium hydride (120 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 (450 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-18e1c4ccfecd4c2594b1cff75f7c61ac
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181186B2

Reaction notes

Loading…