HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetramethyltin → 1-[5-(4-Fluoro-phenyl)-2-methyl-thiazol-4-yl]-1-{(s)-2-[(5-methyl-pyrimidin-2-ylamino)-methyl]-pyrrolidin-1-yl}-methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetramethyltin | HCID 11661 | — |
| Reactant | Lithium Chloride | HCID 433294 | — |
| Reactant | 1-{(S)-2-[(5-Bromo-pyrimidin-2-ylamino)methyl]-pyrrolidin-1-yl}-1-[5-(4-fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanone | HCID 67089741 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 1-[5-(4-Fluoro-phenyl)-2-methyl-thiazol-4-yl]-1-{(s)-2-[(5-methyl-pyrimidin-2-ylamino)-methyl]-pyrrolidin-1-yl}-methanone | HCID 67090181 | — |
Reaction Conditions
| Temperature | 100 °C |
|---|
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07919507B2 |
| Source dataset | uspto-grants-2011_04 |
| ORD ID | ord-fe95538a9f2749fbaf179a5a38bdaaa1 |
| Source note | uspto-grants-2011_04 |