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 18109

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-4893d11d1a2144649e424973006797cd
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741329B2

Linked notes

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