HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → 2-[4-(1-Methyl-6-oxo-1,6-dihydro-[4,4']bipyrimidinyl-2-yloxy)piperidin-1-yl]benzaldehyde
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | o-Fluorobenzaldehyde | HCID 67970 | — |
| Reactant | 1-methyl-2-(piperidin-4-yloxy)-1H-[4,4']bipyrimidinyl-6-one | HCID 67977650 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | 2-[4-(1-Methyl-6-oxo-1,6-dihydro-[4,4']bipyrimidinyl-2-yloxy)piperidin-1-yl]benzaldehyde | HCID 86669146 | 52.3% |
Reaction Conditions
| Temperature | 120 °C |
|---|
Reaction Steps
To a mixture of 1-methyl-2-(piperidin-4-yloxy)-1H-[4,4′]bipyrimidinyl-6-one (1.00 g, 3.48 mmol) and 2-fluorobenzaldehyde (475 mg, 3.83 mmol) in dimethyl sulfoxide (3.50 ml) was added potassium carbonate (1.44 g, 10.4 mmol). The mixture was stirred at 120° C. for 4 hours. The mixture was partitioned between water and chloroform. The organic layer was washed with water (three times), dried over sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent; ethyl acetate) to afford 2-[4-(1-methyl-6-oxo-1,6-dihydro-[4,4′]bipyrimidinyl-2-yloxy)piperidin-1-yl]benzaldehyde as a yellow solid (711 mg, 1.82 mmol, 52%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09006232B2 |
| Source dataset | uspto-grants-2015_04 |
| ORD ID | ord-0fee3f999b644fa2b2ef5dd27ce5ed67 |
| Source note | uspto-grants-2015_04 |