HuagongsheHuagongshe Chemistry Print Report · For research reference only
Purine → HCID 21940652, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Purine | HCID 1044 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Iodobenzene | HCID 11575 | — |
| Reactant | trans-N,N'-dimethyl-1,2-cyclohexanediamine | HCID 2733821 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl acetate hexane | HCID 21226206 | — |
| Product | HCID 21940652 | HCID 21940652 | 69.3% |
Reaction Steps
Using the general procedure, purine (0.120 g, 1.00 mmol) was coupled with iodobenzene (225 μL, 2.00 mmol) using CuI (9.5 mg, 0.050 mmol, 5.0 mol %), Cs2CO3 (2.1 mmol), trans-N,N′-dimethyl-1,2-cyclohexanediamine (32 μL, 0.20 mmol, 20 mol %) and dimethylformamide (1.0 mL) to give the crude product. Column chromatography (2×1 5 cm, hexane:ethyl acetate 1:2) provided 0.136 g (69% yield) of the product as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.00 (d, J=0.9 Hz, 1H), 7.52 (m, 3H), 7.42 (m, 5H), 6.73 (dd, J=0.6 Hz and J=3.3 Hz, 1H), 7.60 (m, 2H), 7.48 (m, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07115784B2 |
| Source dataset | uspto-grants-2006_10 |
| ORD ID | ord-a430936a5ceb40988565bb05aa61005b |
| Source note | uspto-grants-2006_10 |