Tetramethyltin → 1-[5-(4-Fluoro-phenyl)-2-methyl-thiazol-4-yl]-1-{(s)-2-[(5-methyl-pyrimidin-2-ylamino)-methyl]-pyrrolidin-1-yl}-methanone

HRID 2074410

Reaktionsgleichung

Br[C:2]1[CH:3]=[N:4][C:5]([NH:8][CH2:9][C@@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([C:17]2[N:18]=[C:19]([CH3:29])[S:20][C:21]=2[C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)=[O:16])=[N:6][CH:7]=1.[Cl-].[Li+].[CH3:32][Sn](C)(C)C>CN(C)C=O>[F:28][C:25]1[CH:26]=[CH:27][C:22]([C:21]2[S:20][C:19]([CH3:29])=[N:18][C:17]=2[C:15]([N:11]2[CH2:12][CH2:13][CH2:14][C@H:10]2[CH2:9][NH:8][C:5]2[N:4]=[CH:3][C:2]([CH3:32])=[CH:7][N:6]=2)=[O:16])=[CH:23][CH:24]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To the compound of Example 194 (0.36 g) in dimethylformamide was added lithium chloride (0.096 g), tetramethyl tin (0.126 ml) and dichlorobis(triphenylphosphine) palladium (0) (0.035 g) and the resulting mixture heated at 100° C. under argon for 18 h. The reaction was then evaporated, diluted with dichloromethane, filtered and the filtrate washed with water, dried and evaporated. Chromatography of the residue on silica gel, eluting with methanol-dichloromethane mixtures, afforded the title product (0.2 g) as a yellow amorphous solid. Mass Spectrum (API+): Found 412 (MH+). C21H22FN5OS requires 411.

Aufarbeitung

customThe reaction was then evaporated
additiondiluted with dichloromethane
filtrationfiltered
washthe filtrate washed with water
customdried
customevaporated
washChromatography of the residue on silica gel, eluting with methanol-dichloromethane mixtures

Quellen und Nachweise

ORD-Eintrag: ord-fe95538a9f2749fbaf179a5a38bdaaa1
Quelldatensatz: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07919507B2

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