Acetic Acid → HCID 25213228, compound

HRID 2194774Notes

Reaction equation

HRID 2194774 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:34]=[C:35]([CH3:37])[CH:36]=1)[C:6]([C:8]1[N:13]([CH2:14][CH2:15][O:16][C:17](=[O:19])[NH2:18])[C:12](=[O:20])[N:11](CC2C=CC(OC)=CC=2)[C:10](=[O:30])[C:9]=1[CH:31]([CH3:33])[CH3:32])=[O:7])#[N:2].C(O)(=O)C.O>CC#N>[C:1]([C:3]1[CH:4]=[C:5]([CH:34]=[C:35]([CH3:37])[CH:36]=1)[C:6]([C:8]1[N:13]([CH2:14][CH2:15][O:16][C:17](=[O:19])[NH2:18])[C:12](=[O:20])[NH:11][C:10](=[O:30])[C:9]=1[CH:31]([CH3:33])[CH3:32])=[O:7])#[N:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 58203529HCID 58203529, compound

Product 1

HCID 25213228HCID 25213228, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  1. concentrationThe reaction mixture concentrated down
  2. additionEthyl acetate was added
  3. washthe mixture was washed with brine
  4. concentrationThe organic layer was concentrated down
  5. custompurified (silica gel, 20-80% EtOAc /hexane)

Sources & evidence

ORD record
ord-68dc7fac74a64c8fb6c9b73b90a57ccd
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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