(+/-)-5-(9,10-Dihydro-4-hydroxy-2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-yl)-1-methyl-2,4(1H,3H)-pyrimidinedione → HCID 70112978, compound

HRID 324454Notes

Reaction equation

HRID 324454 reaction equation
O[C:2]1([C:17]2[C:18](=[O:25])[NH:19][C:20](=[O:24])[N:21]([CH3:23])[CH:22]=2)[C:8]2[N:9]=[C:10]([CH3:12])[O:11][C:7]=2[CH2:6][CH2:5][C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]1=2>FC(F)(F)C(O)=O>[CH3:12][C:10]1[O:11][C:7]2[CH:6]=[CH:5][C:4]3[CH:13]=[CH:14][CH:15]=[CH:16][C:3]=3[CH:2]([C:17]3[C:18](=[O:25])[NH:19][C:20](=[O:24])[N:21]([CH3:23])[CH:22]=3)[C:8]=2[N:9]=1

Participants

3

Reactant 1

HCID 70113472(+/-)-5-(9,10-Dihydro-4-hydroxy-2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-yl)-1-methyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 70112978HCID 70112978, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A stirred solution of the product from step (ii) (280 mg) in trifluoroacetic acid (5 ml), was heated under reflux for 96 h and evaporated. The residue was slurried in toluene and evaporated (twice). Purification was by flash chromatography eluting 50% acetone in isohexane, followed by a second column eluting with 4% ethanol in dichloromethane to give a yellow solid. Yield 75 mg. Used directly in the next step.

Workup

  1. temperatureunder reflux for 96 h
  2. customevaporated
  3. customevaporated (twice)
  4. customPurification
  5. washeluting 50% acetone in isohexane
  6. washeluting with 4% ethanol in dichloromethane
  7. customto give a yellow solid

Sources & evidence

ORD record
ord-b488002cf17345908f01d8d9891489b6
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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