HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → tert-Butyl (E)-3-{2-hydroxy-8-[(4-isopropyl-1,3-thiazol-2-yl)methoxy]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | tert-Butyl (triphenylphosphoranylidene) acetate | HCID 256127 | — |
| Reactant | 2-Hydroxy-8-[(4-isopropyl-1,3-thiazol-2-yl)methoxy]-4-oxo-4 H-pyrido[1,2-a]-pyrimidine-3-carbaldehyde | HCID 135724429 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | tert-Butyl (E)-3-{2-hydroxy-8-[(4-isopropyl-1,3-thiazol-2-yl)methoxy]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate | HCID 136347719 | 62.4% |
Reaction Conditions
| Temperature | 100 °C |
|---|
Reaction Steps
2-Hydroxy-8-[(4-isopropyl-1,3-thiazol-2-yl)methoxy]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-carbaldehyde (45 mg, 0.13 mmol) dissolved in tetrahydrofuran (2 ml) and dimethylformamide (1 ml) was added with (tert-butoxycarbonylmethylene)triphenyl-phosphorane (60 mg, 0.16 mmol) and refluxed by heating at 100° C. for 2 hours. The reaction solution was returned to room temperature and concentrated under reduced pressure, and the residue was purified by thin layer silica gel chromatography (chloroform:methanol=20:1) to obtain 36 mg (62%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07056917B2 |
| Source dataset | uspto-grants-2006_06 |
| ORD ID | ord-3bcf1357faca44ca90a8bfecd44121cc |
| Source note | uspto-grants-2006_06 |