Trifluoroacetic acid → HCID 178492149, compound

HRID 1243190Notes

Reaction equation

HRID 1243190 reaction equation
C([Si](C)(C)[O:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[C:18]3=[N:19][C:20]([NH:23][C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=4)=[N:21][CH:22]=[C:17]3[CH2:16][N:15]([C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=3)[C:14]2=[O:40])[CH2:9][CH2:8]1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl.C(OCC)(=O)C>[CH3:39][O:38][C:35]1[CH:36]=[CH:37][C:32]([N:15]2[CH2:16][C:17]3[C:18](=[N:19][C:20]([NH:23][C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=4)=[N:21][CH:22]=3)[N:13]([C@H:10]3[CH2:11][CH2:12][C@H:7]([OH:6])[CH2:8][CH2:9]3)[C:14]2=[O:40])=[CH:33][CH:34]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178492151HCID 178492151, compound

Product 1

HCID 178492149HCID 178492149, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-[trans-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-3-(4-methoxy-phenyl)-7-(4-methoxy-phenylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (0.14 g, 0.15 mmol) (from Example 20a supra) in dichloromethane (5 mL) was added trifluoroacetic acid (2.5 mL) at 0° C. The mixture was stirred at 0° C. for 2 hours. The reaction mixture was diluted with ethyl acetate (15 mL) and washed with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography eluting with ethyl acetate to give crude product which was recrystallized from ethyl acetate-hexanes to give 3-(4-methoxy-phenyl)-1-(trans-4-hydroxy-cyclohexyl)-7-(4-methoxy-phenylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one. (Yield 61 mg, 55%).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography
  6. washeluting with ethyl acetate
  7. customto give crude product which
  8. customwas recrystallized from ethyl acetate-hexanes

Sources & evidence

ORD record
ord-158c8b5e3513417f948c7ebee6e50b8c
Source dataset
uspto-grants-2006_10
Patent number
US07115740B2

Reaction notes

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