Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | HCID 58203529 | HCID 58203529 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 25213228 | HCID 25213228 | 56.2% |
Reaction Steps
Ceric ammonium nitrate (156 mg, 0.189 mmol, 3 eq.) was added to carbamic acid 2-[6-(3-cyano-5-methyl-benzoyl)-5-isopropyl-3-(4-methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-ethyl ester (32 mg, 0.063 mmol, 1.0 eq.) in a mixture of MeCN (1 mL), acetic acid (0.4 mL) and water (0.2 mL). The reaction mixture was stirred at room temperature for 10 minutes. The reaction mixture concentrated down. Ethyl acetate was added and the mixture was washed with brine. The organic layer was concentrated down and purified (silica gel, 20-80% EtOAc /hexane) to give a white solid (13.6 mg, 56%). 1H NMR (300 MHz, d6 DMSO): δ 11.52 (s, 1H), 8.43 (s, 1H), 8.22 (s, 1H), 8.09 (s, 1H), 3.92 (m, 1H), 3.81 (m, 2H), 3.22 (m, 1H), 2.44 (s, 3H), 2.08 (m, 1H), 1.04 (dd, 6H).
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-68dc7fac74a64c8fb6c9b73b90a57ccd |
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| Source note | uspto-grants-2012_12 |
|---|