Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Iodoethane | HCID 6340 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 67050517 | HCID 67050517 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 25215196 | HCID 25215196 | 37% |
Reaction Steps
6-Chloro-1-(5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yl)-1H-indole-4-carbonitrile (35 mg, 0.113 mmol, 1.0 eq.) was dissolved in 0.5 mL DMF. Potassium carbonate (16 mg, 1 eq.) was added and the reaction mixture was stirred at room temperature for 10 minutes. EtI (9.1 μL, 1 eq.) was added. The reaction mixture was stirred at room temperature for 2 hours. Ethyl acetate was added to the reaction mixture, followed by washing with brine. The organic layer was concentrated and purified (silica gel, 0-80% EtOAC/hexane) to give a white powder (14 mg, 37%). LC-MS shows 335.0 (M−1). 1H NMR (300 MHz, CDCl3): δ 9.37 (br, 1 H), 8.05 (s, 1H), 7.08 (m, 2H), 6.80 (d, 1H), 3.58 (m, 1H), 3.17 (m, 1H), 2.62 (s, 3H), 1.88 (m, 1H), 1.17 (dd, 6H), 1.02 (t, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08334295B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-4360f29a60dc49a79c6935d0665f57ce |
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| Source note | uspto-grants-2012_12 |
|---|