Isopropyl iodide → HCID 86723844, compound

HRID 576743Notes

Reaction equation

[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([N:9]2[CH:14]=[CH:13][C:12](=[O:15])[NH:11][C:10]2=[O:16])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[CH:21](I)([CH3:23])[CH3:22].[Cl-].[NH4+]>CN(C)C=O>[CH:21]([N:11]1[C:12](=[O:15])[CH:13]=[CH:14][N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:17])[F:18])[CH:4]=2)[C:10]1=[O:16])([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 1-(3-trifluoromethylphenyl)pyrimidin-2,4(1H,3H)-dione (prepared in Reference Example 98 or 99) (135.0 mg) in N,N-dimethy formamide (5.0 ml) were added at room temperature sodium hydride (25.3 mg) and isopropyl iodide (265 μl) and the resulting mixture was stirred at 110° C. for two hours. To the reaction mixture was added saturated aqueous ammonium chloride solution (30.0 ml), and the resulting mixture was extracted with ethyl acetate (20 ml×2) and the organic layer was washed with water (20 ml×2) and saturated saline (20 ml), dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to afford 3-isopropyl-1-(3-trifluoromethylphenyl)pyrimidin-2,4(1H,3H)-dione (122.5 mg).

Workup

extractionthe resulting mixture was extracted with ethyl acetate (20 ml×2)
washthe organic layer was washed with water (20 ml×2) and saturated saline (20 ml)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record: ord-0dc22554bc1948eb9b1a46e3ae0da4f8
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040516B2

Reaction notes

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