Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Lithium Chloride | HCID 433294 | — |
| Reactant | tert-butyl N-(5-(tributylstannyl)-1,3-thiazol-2-yl)carbamate | HCID 2763269 | — |
| Reactant | 7-bromoquinazoline | HCID 11195146 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Product | HCID 86613780 | HCID 86613780 | 46.4% |
Reaction Steps
To a stirred mixture of flame-dried LiCl (45 mg, 1052 μmol), 7-bromoquinazoline (22 mg, 105 μmol), and Pd(Ph3P)4 (6.1 mg, 5.3 μmol), was added a solution of tert-butyl 5-(tributylstannyl)thiazol-2-ylcarbamate (77 mg, 158 μmol) in DMF (1.50 mL, 19372 μmol). The resulting mixture was stirred at 80° C. overnight. The mixture was concentrated, and the crude residue was dissolved in DCM and mixed with SiO2. The solvent was evaporated, and the residue was purified with flash column chromatography (pure DCM→5% MeOH in DCM) followed by washing with ether to obtain the desired product tert-butyl 5-(quinazolin-7-yl)thiazol-2-ylcarbamate (16 mg, 46%) as a pale yellow solid. LCMS (API-ES) m/z (%): 329.4 (100%, M++H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07514566B2 |
|---|
| Source dataset | uspto-grants-2009_04 |
|---|
| ORD ID | ord-eccd56c51b4245ec94614a091a2bcf95 |
|---|
| Source note | uspto-grants-2009_04 |
|---|
