Morpholine → HCID 136197590, compound

HRID 327059Notes

Reaction equation

HRID 327059 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.S([O-])(=O)(=O)C.CS(O[CH2:17][CH2:18][O:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([O:41][CH2:42][CH2:43][CH3:44])=[C:25]([C:27]2[NH:28][C:29](=[O:40])[C:30]3[N:35]([CH3:36])[N:34]=[C:33]([CH2:37][CH2:38][CH3:39])[C:31]=3[N:32]=2)[CH:26]=1)(=O)=O>C(#N)C>[CH3:36][N:35]1[C:30]2[C:29](=[O:40])[NH:28][C:27]([C:25]3[CH:26]=[C:21]([CH2:20][O:19][CH2:18][CH2:17][N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)[CH:22]=[CH:23][C:24]=3[O:41][CH2:42][CH2:43][CH3:44])=[N:32][C:31]=2[C:33]([CH2:37][CH2:38][CH3:39])=[N:34]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 85257MethanesulfonateHCID 136138673HCID 136138673, compound

Product 1

HCID 136197590HCID 136197590, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Morpholine (0.19 g, 0.0021 mol) was added to a solution of the above mesylate, namely 5-[5-(2-methanesulphonyloxyethoxymethyl)-2-n-propoxyphenyl]-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one, (0.20 g, 0.00042 mol) in acetonitrile (25 ml) and the stirred mixture was heated under reflux for 18 hours. The solvent was removed by evaporation under vacuum, the residue dissolved in saturated aqueous sodium carbonate solution and the solution extracted with ethyl acetate (3×20 ml). The extracts were combined, dried (Na2SO4) and evaporated under vacuum, and the residue was chromatographed on silica gel (4g) using an elution gradient of methanol in dichloromethane (0-2% methanol). Evaporation under vacuum of the appropriate fractions, followed by crystallisation from hexane, gave the title compound as white crystals (0.098 g, 48%), m.p. 65°-66° C. Found C,64.17; H,7.69; N,14.96. C25H35N5O5 requires C,63.94; H,7.51; N,14.91%.

Workup

  1. temperaturethe stirred mixture was heated
  2. temperatureunder reflux for 18 hours
  3. customThe solvent was removed by evaporation under vacuum
  4. dissolutionthe residue dissolved in saturated aqueous sodium carbonate solution
  5. extractionthe solution extracted with ethyl acetate (3×20 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated under vacuum
  8. customthe residue was chromatographed on silica gel (4g)
  9. customEvaporation under vacuum of the appropriate fractions
  10. customfollowed by crystallisation from hexane

Sources & evidence

ORD record
ord-0f758a6e357d493e8c70fde90e71f08c
Source dataset
uspto-grants-1993_12
Patent number
US05272147

Reaction notes

Loading…