Trifluoroacetic acid → 7-(4-Diethylamino-butylamino)-3-(3,5-dimethoxy-phenyl)-1-ethyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one

HRID 1783536Notes

Reaction equation

HRID 1783536 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]([CH2:35][CH3:36])[CH2:30][CH2:31][CH2:32][CH2:33][NH2:34])[CH3:28].FC(F)(F)C(O)=O>C(#N)C>[CH2:27]([N:29]([CH2:35][CH3:36])[CH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:16]1[N:15]=[C:14]2[N:13]([CH2:24][CH3:25])[C:12](=[O:26])[N:11]([C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=3)[CH2:20][C:19]2=[CH:18][N:17]=1)[CH3:28]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 117976N,N-Diethyl-1,4-butanediamineHCID 68858127HCID 68858127, compound

Product 1

HCID 540506487-(4-Diethylamino-butylamino)-3-(3,5-dimethoxy-phenyl)-1-ethyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-oneYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °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-diethylaminobutylamine (0.38 g, 2.66 mmol,) and trifluoroacetic acid (0.31 g, 2.66 mmol) in acetonitrile (6 mL) was heated in a sealed tube at 90° C. for 18 hours. The solvent was removed under reduced pressure and the residue taken up in 1N HCl. The solution was made basic with 50% NaOH and extracted twice with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered, and evaporated. The residue was purified by radial chromatography eluting with a solvent mixture of ethyl acetate/methanol/ethyl (89:10:1 v/v/v) to give 0.34 g (56%) of the titled compound: mp 83-85° C. Mass Spectrum (APCI, 80/20 CH3CN/H2O, Probe=450° C.) (m+1)/z 458.2

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionextracted twice with dichloromethane
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by radial chromatography
  7. washeluting with a solvent mixture of ethyl acetate/methanol/ethyl (89:10:1 v/v/v)

Sources & evidence

ORD record
ord-cf021851595c400e8dd96764b8eda5ba
Source dataset
uspto-grants-2009_03
Patent number
US07501425B1

Reaction notes

Loading…