HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-Chloro-N-((1-(4-(2-oxopyrimidin-1(2H)-yl)phenyl)-1H-1,2,3-triazol-4-yl)methyl)thiophene-2-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | 5-chloro-N-(prop-2-yn-1-yl)thiophene-2-carboxamide | HCID 3851180 | — |
| Reactant | 1-(4-azidophenyl)pyrimidin-2(1H)-one | HCID 59260078 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 5-Chloro-N-((1-(4-(2-oxopyrimidin-1(2H)-yl)phenyl)-1H-1,2,3-triazol-4-yl)methyl)thiophene-2-carboxamide | HCID 24990942 | — |
Reaction Steps
1-(4-Azidophenyl)pyrimidin-2(1H)-one (2.4, 20 mg, 0.09 mmol) was dissolved in 5 mL methanol. To it were added 5-chloro-N-(prop-2-ynyl)thiophene-2-carboxamide (compound 1.4, 18 mg, 0.09 mmol), DBU (26 μL, 0.18 mmol) and CuI (17 mg, 0.09 mmol). The mixture was stirred for 2 hrs at RT, diluted with 30 mL acetonitrile, filtered through celite, concentrated in vacuo and subjected to prep HPLC to isolate the title compound. MS found for C18H13ClN6O2S (M+H)+ 413.0, 415.0 (Cl pattern).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07696352B2 |
| Source dataset | uspto-grants-2010_04 |
| ORD ID | ord-9203fe5a86314ba0ad197936a84a75a3 |
| Source note | uspto-grants-2010_04 |