Phenol → 1,6-Dihydro-5-(2-hydroxyphenyl)-1-methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-one

HRID 1532113Notes

Reaction equation

HRID 1532113 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[NH:12][C:13](=[O:24])[C:14]2[N:19]([CH3:20])[N:18]=[C:17]([CH2:21][CH2:22][CH3:23])[C:15]=2[N:16]=1)C=C.C1(O)C=CC=CC=1.N1CCCCC1>C(O)C>[OH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[NH:12][C:13](=[O:24])[C:14]2[N:19]([CH3:20])[N:18]=[C:17]([CH2:21][CH2:22][CH3:23])[C:15]=2[N:16]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 8082PiperidineHCID 1357385485-(2-Allyloxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Product 1

HCID 1355465171,6-Dihydro-5-(2-hydroxyphenyl)-1-methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-(2-allyloxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (0.25 g, 0.0008 mol), phenol (0.145 g, 0.0015 mol), piperidine (0.131 g, 0.0015 mol) and tetrakis-(triphenylphosphine)palladium(0) (0.046 g, 0.00004 mol) in absolute ethanol (5 ml) was refluxed overnight under nitrogen. The mixture was allowed to cool, the solvent evaporated under vacuum and the residue dissolved in ethyl acetate (40 ml). This solution was washed with water (3×10 ml), 1M HCl (3×10 ml) and brine (1×10 ml). After drying (Na2SO4) and filtration, the filtrate was evaporated under vacuum to give the crystallisation from ethyl acetate/pentane, m.p 233-238° C. Found: C, 63.17; H, 5.65; N, 19.52. C15H16N4O2 requires C, 63.36; H, 5.67; N, 19.71%.

Workup

  1. temperaturewas refluxed overnight under nitrogen
  2. temperatureto cool
  3. customthe solvent evaporated under vacuum
  4. dissolutionthe residue dissolved in ethyl acetate (40 ml)
  5. washThis solution was washed with water (3×10 ml), 1M HCl (3×10 ml) and brine (1×10 ml)
  6. customAfter drying
  7. filtration(Na2SO4) and filtration
  8. customthe filtrate was evaporated under vacuum
  9. customto give
  10. customthe crystallisation from ethyl acetate/pentane, m.p 233-238° C

Sources & evidence

ORD record
ord-298be2fe37f84a69bbffdff05b96ec1f
Source dataset
uspto-grants-2001_03
Patent number
US06200980B1

Reaction notes

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