2-methoxy-7-(pyrimidin-5-yl)-9H-xanthen-9-one → 2-methoxy-7-(pyrimidin-5-yl)-9-vinyl-9H-xanthen-9-ol

HRID 455687

Reaction equation

[CH:1]([Mg]Cl)=[CH2:2].[CH3:5][O:6][C:7]1[CH:20]=[CH:19][C:18]2[O:17][C:16]3[C:11](=[CH:12][C:13]([C:21]4[CH:22]=[N:23][CH:24]=[N:25][CH:26]=4)=[CH:14][CH:15]=3)[C:10](=[O:27])[C:9]=2[CH:8]=1>C1COCC1>[CH3:5][O:6][C:7]1[CH:20]=[CH:19][C:18]2[O:17][C:16]3[C:11](=[CH:12][C:13]([C:21]4[CH:26]=[N:25][CH:24]=[N:23][CH:22]=4)=[CH:14][CH:15]=3)[C:10]([CH:1]=[CH2:2])([OH:27])[C:9]=2[CH:8]=1

Participants

Conditions

Temperature: -10 °C

Procedure

A solution of vinylmagnesium chloride (1.6M solution in THF; 0.82 mL, 1.314 mmol) was added dropwise to a solution of 2-methoxy-7-(pyrimidin-5-yl)-9H-xanthen-9-one (200 mg, 0.657 mmol) in THF (10 mL) at −78° C. After 30 min, the reaction mixture was allowed to warm to −10° C. and was then quenched with saturated aqueous ammonium chloride. The reaction was extracted with EtOAc, and the organic phase was dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by chromatography to give 2-methoxy-7-(pyrimidin-5-yl)-9-vinyl-9H-xanthen-9-ol as a pale yellow gum.

Workup

customwas then quenched with saturated aqueous ammonium chloride
extractionThe reaction was extracted with EtOAc
dry with materialthe organic phase was dried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by chromatography

Sources & evidence

ORD record: ord-384740b203e645908800479fe166b8b2
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497264B2

Linked notes

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