HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium ethoxide → 7-[(E)-2-(3-Cyclopropylmethoxy-4-methoxyphenyl)-1-ethenyl]-6-[4-(trifluoro methyl)-phenyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium ethoxide | HCID 2723922 | — |
| Reactant | 3-(Cyclopropylmethoxy)-4-methoxybenzaldehyde | HCID 22246623 | — |
| Reactant | 7-Methyl-6-[4-(trifluoromethyl)phenyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one | HCID 66752802 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | 7-[(E)-2-(3-Cyclopropylmethoxy-4-methoxyphenyl)-1-ethenyl]-6-[4-(trifluoro methyl)-phenyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one | HCID 44467313 | 42.9% |
Reaction Steps
The title compound was synthesized by condensation of Intermediate 5 (400 mg, 1.350 mmol) with 3-cyclopropylmethoxy-4-methoxybenzaldehyde (417 mg, 2.025 mmol) in presence of sodium ethoxide (183 mg, 2.701 mmol) in ethanol (20 ml) according to the procedure described in Example 24 to give 289 mg of the desired product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 0.23-0.30 (m, 2H), 0.50-0.58 (m, 2H), 1.12-1.18 (m, 1H), 3.72-3.80 (m, 5H), 6.60 (d, J=15.6 Hz, 1H) 6.94-7.00 (m, 3H), 7.48-7.53 (m, 1H), 7.58-7.64 (m, 2H), 7.78-7.84 (m, 3H), 7.98-8.05 (m, 1H); ESI-MS (m/z) 499.12 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08119647B2 |
| Source dataset | uspto-grants-2012_02 |
| ORD ID | ord-0b9641c3daa8443a8412f916017d74fc |
| Source note | uspto-grants-2012_02 |