HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium ethoxide → 7-[(E)-2-(3-Methoxy-2-propoxyphenyl)-1-ethenyl]-6-[4-(trifluoromethoxy)phenyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium ethoxide | HCID 2723922 | — |
| Reactant | 3-Methoxy-2-propoxybenzaldehyde | HCID 3159325 | — |
| Reactant | HCID 66753265 | HCID 66753265 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | 7-[(E)-2-(3-Methoxy-2-propoxyphenyl)-1-ethenyl]-6-[4-(trifluoromethoxy)phenyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one | HCID 44467535 | 47.9% |
Reaction Steps
The title compound was prepared by condensation of Intermediate 15 (400 mg, 1.225 mmol) with 3-methoxy-2-propoxybenzaldehyde (333 mg, 1.716 mmol) in the presence of sodium ethoxide (176 mg, 2.301 mmol) in ethanol (25 ml) according to the procedure outlined in Example 24 to give 295 mg of the desired product as a light yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 0.94 (t, J=7.2 Hz, 3H), 1.53 (q, J=6.9 Hz, 2H), 3.31 (s, 1H), 3.77 (s, 3H), 3.80 (s, 1H), 6.91-6.99 (m, 4H), 7.40-7.46 (m, 4H), 7.50 (d, J=4.8 Hz, 1H), 7.95-8.07 (m, 2H); ESI-MS (m/z) 503.51 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08119647B2 |
| Source dataset | uspto-grants-2012_02 |
| ORD ID | ord-c3a9da6f3ab74e0ebfac678c93f75445 |
| Source note | uspto-grants-2012_02 |