Methyl iodide → 1,5,5-Trimethyl-2-(5-phenylethynyl-pyridin-2-yl)-pyrazolidin-3-one

HRID 240484Notes

Reaction equation

[CH3:1][C:2]1([CH3:22])[NH:6][N:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:9][N:8]=2)[C:4](=[O:21])[CH2:3]1.[C:23]([O-])([O-])=O.[K+].[K+].IC>C(#N)C>[CH3:23][N:6]1[C:2]([CH3:22])([CH3:1])[CH2:3][C:4](=[O:21])[N:5]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][N:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

(35 mg, 120 μmol) 5,5-Dimethyl-2-(5-phenylethynyl-pyridin-2-yl)-pyrazolidin-3-one (Example 1, step 4) was dissolved in ACN (2 ml). K2CO3 (33 mg, 240 μmol, 2 equiv.) and iodomethane (22 mg, 156 μmol, 1.3 equiv.) were added and the mixture was stirred for 16 hours at 80° C. The reaction mixture was evaporated and extracted with water and two times with ethyl acetate. The organic layers were extracted with brine, dried with sodium sulfate and evaporated to dryness. The crude product was purified by reverse phase column chromatography. The desired 1,5,5-trimethyl-2-(5-phenylethynyl-pyridin-2-yl)-pyrazolidin-3-one (18 mg, 49% yield) was obtained as a colorless oil, MS: m/e=306.2 (M+H+).

Workup

customThe reaction mixture was evaporated
extractionextracted with water and two times with ethyl acetate
extractionThe organic layers were extracted with brine
dry with materialdried with sodium sulfate
customevaporated to dryness
customThe crude product was purified by reverse phase column chromatography

Sources & evidence

ORD record: ord-f7883b0fe42349b8a0abaa8d55a43b34
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648088B2

Reaction notes

Loading…