2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl- → Acridinedione

HRID 1018754Notes

Reaction equation

HRID 1018754 reaction equation
C1(C)C=C(C)C=C(C)C=1[C:9]1[C:10](=[O:24])[C:11](=[O:23])[C:12]2[C:21]([CH:22]=1)=[N:20][C:19]1[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH:13]=2.CN1C(=O)N(C)CCC1>C1COCC1>[C:11]1(=[O:23])[C:12]2[C:21](=[N:20][C:19]3[C:14]([CH:13]=2)=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:22]=[CH:9][C:10]1=[O:24]

Participants

4

Reactant 2

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 68991988Mesityl-acridine-quinone

Product 1

HCID 22117053AcridinedioneYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an atmosphere of argon, 151.4 mg (2.45×10−4 mol) of mesityl-acridine-quinone 43 was dissolved in 30 mL of 0.1M SmI2 in THF. Then, 2.2 mL (18.2 mmol) of DMPU were added dropwise. The reaction mixture was refluxed for 24 hr. Filtration to remove a precipitate and evaporation of solvent yielded an orange oil, which was purified by column chromatography on silica gel with 5% MeOH in CH2Cl2 to afford 48.7 mg (45%) of acridine-quinone 44 as an orange glassy solid: 1H NMR (300 MHz, DMSO-d6, TMS) δ8.54 (d, J=8 Hz, 2H), 7.96 (t, J=7 Hz, 2H), 7.92 (d, J=7 Hz, 1H), 7.79 (d, J=8 Hz, 2H), 7.7-7.6 (m, 3H), 7.51 (t, J=8 Hz, 2H), 6.01 (s, 1H), 4.20 (t, J=6 Hz, 2H), 4.13 (t, J=7 Hz, 2H), 2.1-1.9 (m, 4H), 1.7-1.6 (m, 2H).

Workup

  1. temperatureThe reaction mixture was refluxed for 24 hr
  2. filtrationFiltration
  3. customto remove
  4. customa precipitate and evaporation of solvent
  5. customyielded an orange oil, which
  6. customwas purified by column chromatography on silica gel with 5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-0129f61ce7bd462e9a7704406ead663c
Source dataset
uspto-grants-2002_11
Patent number
US06482943B1

Reaction notes

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