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

HRID 862901Notes

Reaction equation

HRID 862901 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.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[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

6

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-oneYield 10%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 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(O) (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 crude product. The title phenol (0.021 g, 10%) was obtained after trituration with diethyl ether and crystallisation from ethyl acetate/pentane, m.p. 233°-238° C. Found: C,63.17; H,5.65; N, 19.52. C15 H16N4O2 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 the crude product

Sources & evidence

ORD record
ord-b8d92448ea6b4c7da8449bcef63a4328
Source dataset
uspto-grants-1998_02
Patent number
US05719283

Reaction notes

Loading…