HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Aminopyrimidine → 8-Methoxy-2-oxo-2H-chromene-3-carboxylic acid pyrimidin-4-ylamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Aminopyrimidine | HCID 68958 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 8-Methoxy-2-oxo-2H-chromene-3-carboxylic acid | HCID 234562 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 8-Methoxy-2-oxo-2H-chromene-3-carboxylic acid pyrimidin-4-ylamide | HCID 86650362 | 11.2% |
Reaction Steps
DIEA (0.044 mL, 0.25 mmol) was added to 8-methoxy-3-carboxy-coumarin (0.030 g, 0.14 mmol) and HATU (0.095 g, 0.25 mmol) in 1 mL of dimethylformamide (DMF) with constant stirring at room temperature until a clear solution resulted. Subsequently, pyrimidin-4-ylamine (0.009 g, 0.09 mmol) was added and allowed to react overnight, when a solid precipitated out of solution. The precipitate was filtered and dried under suction and then in vacuo to give 0.003 g of 1541E in an 11% yield: LCMS (ESI) m/z 298 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08642788B2 |
| Source dataset | uspto-grants-2014_02 |
| ORD ID | ord-2d51c4b1ed764bf48d22b69a4e99b14e |
| Source note | uspto-grants-2014_02 |