Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzyl mercaptan | HCID 7509 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | HCID 86687760 | HCID 86687760 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Product | HCID 86687759 | HCID 86687759 | 41.8% |
Reaction Steps
The reaction mixture from step 4 was treated with Pd2(dba)3 (0.023 g, 0.025 mmol), Xantphos (0.029 g, 0.051 mmol), and n,n-diisopropylethylamine (0.530 ml, 3.04 mmol), and was heated to 60° C. Benzyl mercaptan (0.120 ml, 1.012 mmol) was added, and the reaction mixture was allowed to stir for one hour at 60° C. LC/MS showed mostly product, so the reaction mixture was concentrated. Purification of the crude residue by silica gel column chromatography (0-75% EtOAc/heptane) gave 7-(benzylthio)-4-(4-(3-fluorooxetan-3-yl)-2-methoxyphenyl)-2-methylquinazoline (0.189 g, 0.423 mmol, 41.8% yield) with minor impurities. (M+H)+=447.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09012443B2 |
|---|
| Source dataset | uspto-grants-2015_04 |
|---|
| ORD ID | ord-2157565336c745e18473f4db2dcefcf8 |
|---|
| Source note | uspto-grants-2015_04 |
|---|
