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 2113539Notes

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-344b2b0903d04939bbe441d0e76472ce
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432270B2

Reaction notes

Loading…