Ethyl Acetate → HCID 86723889, compound

HRID 576781Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([N:8]2[C:13]([CH3:14])=[C:12]([C:15]3[N:19]([C:20]4[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=4)[N:18]=[CH:17][CH:16]=3)[C:11](=[O:28])[N:10]([CH3:29])[C:9]2=[O:30])[CH:5]=[CH:6][CH:7]=1.[C:31](OCC)(=O)[CH3:32]>O1CCCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.C[CH2-].C[CH2-].[Zn+2]>[CH3:29][N:10]1[C:11](=[O:28])[C:12]([C:15]2[N:19]([C:20]3[CH:21]=[CH:22][C:23]([C:24]#[N:25])=[CH:26][CH:27]=3)[N:18]=[CH:17][CH:16]=2)=[C:13]([CH3:14])[N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH2:31][CH3:32])[CH:3]=2)[C:9]1=[O:30]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-[5-[1-(3-bromophenyl)-3,6-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl]-1H-pyrazol-1-yl]benzonitrile (prepared in Example 34) (15.5 mg) and bis(tri-t-butylphosphine)palladium (1.0 mg) in tetrahydrofuran (1.0 ml) was added zinc diethyl (1.0 M normal hexane solution, 0.06 ml) and the resulting mixture was stirred at 60° C. for thirty minutes. To the reaction mixture was added ethyl acetate (30 ml) and the mixture was washed with water (10 ml) and saturated saline (10 ml), dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by preparative thin-layer chromatography to afford 4-[5-[3,6-dimethyl-2,4-dioxo-1-(3-ethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl]-1H-pyrazol-1-yl]benzonitrile (3.6 mg).

Workup

washthe mixture was washed with water (10 ml) and saturated saline (10 ml)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by preparative thin-layer chromatography

Sources & evidence

ORD record: ord-cdeeae61bcda4e07a3fad5f826b0c4fa
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040516B2

Reaction notes

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