HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethanol → 2-Methyl-3-[4-(trifluoromethoxy)phenyl]-4H-pyrimido[2,1-b][1,3]benzo thiazol-4-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-(Trifluoromethoxy)phenylboronic acid | HCID 2734386 | — |
| Reactant | 4-(2-Methyl-4-oxo-4H-pyrimido[2,1-b][1,3]benzothiazol-3-yl)benzonitrile | HCID 66752654 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 2-Methyl-3-[4-(trifluoromethoxy)phenyl]-4H-pyrimido[2,1-b][1,3]benzo thiazol-4-one | HCID 66753676 | 68.2% |
Reaction Steps
The title compound was prepared by treatment of Step 2 intermediate, Intermediate 22 (2.0 g, 5.845 mmol) with 4-trifluoromethoxyphenylboronic acid (1.684 g, 8.183 mmol) in the presence of Pd[(C6H5)3P]4 (270 mg, 0.233 mmol) and sodium carbonate (3.11 g, 35.07 mmol) in a mixture of toluene, ethanol and water to afford 1.5 g of the desired product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 2.02 (s, 3H), 7.41-7.59 (m, 3H), 7.53-7.56 (m, 3H), 8.03-8.07 (m, 1H), 8.84-8.87 (m, 1H); ESI-MS (m/z) 377.17 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08119647B2 |
| Source dataset | uspto-grants-2012_02 |
| ORD ID | ord-03a4911837324993bd443c073adef635 |
| Source note | uspto-grants-2012_02 |