HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sulfoximine, S,S-dimethyl- → N-(2-benzyloxy-4-fluoro-phenyl)-7-[[dimethyl(oxo)-lambda6-sulfanylidene]amino]-5-methyl-quinazolin-4-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sulfoximine, S,S-dimethyl- | HCID 123119 | — |
| Reactant | 2-(Di-tert-butylphosphino)biphenyl | HCID 2734215 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Reactant | N-(2-benzyloxy-4-fluoro-phenyl)-7-bromo-5-methyl-quinazolin-4-amine | HCID 86718470 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | N-(2-benzyloxy-4-fluoro-phenyl)-7-[[dimethyl(oxo)-lambda6-sulfanylidene]amino]-5-methyl-quinazolin-4-amine | HCID 86718469 | — |
Reaction Steps
3.1 g (7 mmol) of N-(2-benzyloxy-4-fluoro-phenyl)-7-bromo-5-methyl-quinazolin-4-amine, 0.8 g (8.8 mmol) dimethylsulphoximine (IV.1), 0.4 g (1.4 mmol) 2-(di-t-butylphosphino) biphenyl, 0.5 g (0.5 mmol) Pd2dba3 and 1.0 g (10.2 mmol) sodium tert-butoxide in dioxane are heated to 80° C. for 4.5 h. After cooling to RT the reaction mixture is filtered, diluted with water and extracted with EtOAc. The organic layers are pooled, dried and evaporated. The residue is purified by FC giving rise to N-(2-benzyloxy-4-fluoro-phenyl)-7-[[dimethyl(oxo)-λ6-sulfanylidene]amino]-5-methyl-quinazolin-4-amine.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09139577B2 |
| Source dataset | uspto-grants-2015_09 |
| ORD ID | ord-0f60af2822a04e1fa1a2b5c25134b379 |
| Source note | uspto-grants-2015_09 |