Trifluoroacetic acid → HCID 54113892, compound

HRID 1783537Notes

Reaction equation

HRID 1783537 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:11]2[CH2:20][C:19]3[C:14](=[N:15][C:16](S(C)=O)=[N:17][CH:18]=3)[N:13]([CH2:24][CH3:25])[C:12]2=[O:26])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[CH2:27]([N:29]([CH2:40][CH3:41])[CH2:30][CH2:31][O:32][C:33]1[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=1)[CH3:28].FC(F)(F)C(O)=O.C(N(CC)CC)C.O(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O>C(#N)C.CCCCCC>[CH2:40]([N:29]([CH2:27][CH3:28])[CH2:30][CH2:31][O:32][C:33]1[CH:34]=[CH:35][C:36]([NH:37][C:16]2[N:15]=[C:14]3[N:13]([CH2:24][CH3:25])[C:12](=[O:26])[N:11]([C:5]4[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=4)[CH2:20][C:19]3=[CH:18][N:17]=2)=[CH:38][CH:39]=1)[CH3:41]

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 4189324-(2-(Diethylamino)ethoxy)anilineHCID 68858127HCID 68858127, compound

Product 1

HCID 54113892HCID 54113892, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-(3,5-dimethoxy-phenyl)-1-ethyl-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one (0.5 g, 1.33 mmol), 4-(2-diethylaminoethoxy)aniline (0.55 g, 2.66 mmol, Helv. Chim. Acta, 1960; 43:1971-1979) and trifluoroacetic acid (0.46 g, 3.98 mmol) in acetonitrile (6 mL) was heated in a sealed tube at 100° C. for 18 hours. The solvent was removed under reduced pressure and the residue dissolved in water. The solution was made basic with 1N NaOH and extracted twice with EtOAc. The combined organic layers were dried over magnesium sulfate, filtered, and evaporated. The residue was suspended in ether (20 mL), triethylamine (0.27 g, 2.66 mmol), and BOC2O (0.32 g, 1.46 mmol) added, and the mixture stirred at ambient temperature for 4 hours. The reaction mixture was diluted with hexane and cooled to 0° C. The insoluble product was collected by filtration and washed with hexane to afford 0.56 g (81%) of the titled compound: mp 139-141° C. Mass Spectrum (APCI, 80/20 CH3CN/H2O, Probe=450° C.) (m+1)/z 521.3

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in water
  3. extractionextracted twice with EtOAc
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. temperaturecooled to 0° C
  8. filtrationThe insoluble product was collected by filtration
  9. washwashed with hexane

Sources & evidence

ORD record
ord-8c1f44645dbe44dbabe802671fe569be
Source dataset
uspto-grants-2009_03
Patent number
US07501425B1

Reaction notes

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