Water → 1-(2-Chloropyrimidin-4-yl)-3-isopropyl-2-oxopyrrolidine-3-carbonitrile

HRID 714787Notes

Reaction equation

[CH:1]([C:4]1([C:10]#[N:11])[CH2:8][CH2:7][NH:6][C:5]1=[O:9])([CH3:3])[CH3:2].[Cl:12][C:13]1[N:18]=[C:17](Cl)[CH:16]=[CH:15][N:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>[Cl:12][C:13]1[N:18]=[C:17]([N:6]2[CH2:7][CH2:8][C:4]([CH:1]([CH3:3])[CH3:2])([C:10]#[N:11])[C:5]2=[O:9])[CH:16]=[CH:15][N:14]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 3-isopropyl-2-oxopyrrolidine-3-carbonitrile (120 mg) obtained in Step B, 2,4-dichloropyrimidine (240 mg), cesium carbonate (510 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (27 mg) in tetrahydrofuran (3 mL) was added tris(dibenzylideneacetone)dipalladium(0) (14 mg), and the mixture was stirred overnight at 100° C. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (160 mg).

Workup

extractionthe mixture was extracted 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 (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-67ce8a098dc24365a3ade93e72085159
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187453B2

Reaction notes

Loading…