HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 3-(3-fluoro-4-morpholinophenyl)-2-(((5-fluoropyridin-3-yl)oxy)methyl)-6-methyl-pyrimidin-4(3H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 2-((5-Fluoropyridin-3-yl)oxy)acetamide | HCID 90022681 | — |
| Reactant | N-(3-fluoro-4-morpholinophenyl)-3-oxobutanamide | HCID 90023295 | — |
| Catalyst | Titanium isopropoxide | HCID 11026 | — |
| Solvent | O-Xylene | HCID 7237 | — |
| Product | 3-(3-fluoro-4-morpholinophenyl)-2-(((5-fluoropyridin-3-yl)oxy)methyl)-6-methyl-pyrimidin-4(3H)-one | HCID 90051695 | 27% |
Reaction Steps
To a mixture of 2-((5-fluoropyridin-3-yl)oxy)acetamide (200 mg, 1.18 mmol) and N-(3-fluoro-4-morpholinophenyl)-3-oxobutanamide (330 mg, 1.18 mmol) in xylene (10 mL) was added titanium tetraisopropanolate (2.7 mg, 9.5 mmol) and the mixture was refluxed for 50 h. The mixture was cooled to rt and 60 mL of EtOAc and 10 mL of water were added. The resulting mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a yellow solid (130 mg, 27%). The compound was characterized by the following spectroscopic data:
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09434695B2 |
| Source dataset | uspto-grants-2016_09 |
| ORD ID | ord-2a99ca492f3e4809b414e5c4b7aa3abf |
| Source note | uspto-grants-2016_09 |