Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 68859604, compound

HRID 1783535Notes

Reaction equation

HRID 1783535 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)[NH:13][C:12]2=[O:24])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[CH2:25]([N:27]([CH2:30][CH2:31][CH2:32][CH2:33][NH2:34])[CH2:28][CH3:29])[CH3:26].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>O1CCOCC1>[CH2:25]([N:27]([CH2:28][CH3:29])[CH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:16]1[N:15]=[C:14]2[NH:13][C:12](=[O:24])[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)[CH3:26]

Participants

5

Reactant 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 117976N,N-Diethyl-1,4-butanediamine2×HCID 570581323-(3,5-dimethoxy-phenyl)-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one

Product 1

HCID 68859604HCID 68859604, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 0.2261 g (0.65 mmol) of 3-(3,5-dimethoxy-phenyl)-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one and 0.103 g (0.71 mmol) of diethylaminobutylamine in 10 mL of dry dioxane was warmed to 60° C. and stirred overnight. To the reaction mixture was added 0.306 g (2.13 mmol) of diethylaminobutylamine and 0.1658 g (0.71 mmol) of camphorsulfonic acid. The reaction mixture was stirred for another 18 hours at 60° C. The reaction solution was concentrated in vacuo, and the residue was partitioned between ethyl acetate and a saturated solution of sodium bicarbonate. The ethyl acetate layer was washed with a saturated solution of sodium bicarbonate, then with water, dried over magnesium sulfate, and concentrated in vacuo. The residue was chromatographed down silica gel, eluting with ethyl acetate/ethanol/triethylamine (9:2:1 v/v/v) to give 0.173 g (62%) of the title compound: mp 203-207° C.

Workup

  1. stirringThe reaction mixture was stirred for another 18 hours at 60° C
  2. concentrationThe reaction solution was concentrated in vacuo
  3. customthe residue was partitioned between ethyl acetate
  4. washThe ethyl acetate layer was washed with a saturated solution of sodium bicarbonate
  5. dry with materialwith water, dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed down silica gel
  8. washeluting with ethyl acetate/ethanol/triethylamine (9:2:1 v/v/v)

Sources & evidence

ORD record
ord-53c699833672443fa5a96b07a82b473a
Source dataset
uspto-grants-2009_03
Patent number
US07501425B1

Reaction notes

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