2,2,2-Trifluoroethanol → HCID 59351535, compound

HRID 1889423Notes

Reaction equation

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

Participants

Reactant 3

HCID 64092,2,2-Trifluoroethanol2×

HCID 5360545Sodium

HCID 59351773HCID 59351773, compound

Product 1

HCID 59351535HCID 59351535, compoundYield 30%

Conditions

Temperature: 100 °C

Procedure

To a mixture of 4′-[(6-chloro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]biphenyl-2-carbonitrile (2.7 g) and 2,2,2-trifluoroethanol (70 mL) was added a solution of sodium (0.28 g) in 2,2,2-trifluoroethanol (10 mL), and the mixture was stirred at 100° C. for 4 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was extracted with chloroform and 1N hydrochloric acid. The chloroform layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as colorless crystals (1.3 g, 30%).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
extractionthe obtained residue was extracted with chloroform and 1N hydrochloric acid
washThe chloroform layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-275d42c28983498d89dc97accd512fa4
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501750B2

Reaction notes

Loading…