Water → 5-(2-Allyloxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

HRID 1532112Notes

Reaction equation

HRID 1532112 reaction equation
[CH2:1]([O:4][C:5]1[CH:25]=[CH:24][CH:23]=[CH:22][C:6]=1[C:7]([NH:9][C:10]1[C:11]([CH2:19][CH2:20][CH3:21])=[N:12][N:13]([CH3:18])[C:14]=1[C:15]([NH2:17])=[O:16])=O)[CH:2]=[CH2:3].[OH-].[Na+].O>C(O)C>[CH2:1]([O:4][C:5]1[CH:25]=[CH:24][CH:23]=[CH:22][C:6]=1[C:7]1[NH:17][C:15](=[O:16])[C:14]2[N:13]([CH3:18])[N:12]=[C:11]([CH2:19][CH2:20][CH3:21])[C:10]=2[N:9]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 536390684-(2-Allyloxybenzamido)-1-methyl-3-n-propyl-pyrazole-5-carboxamide

Product 1

HCID 1357385485-(2-Allyloxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-oneYield 41.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(2-allyloxybenzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide (1.2 g, 0.0035 mol), sodium hydroxide (0.70 g, 0.018 mol), water (34 ml) and ethanol (8 ml) was refluxed for 5 hours. After cooling, the solution was exhaustively extracted with ethyl acetate. The combined extracts were washed with brine (30 ml), dried (Na2SO4), filtered and the solvent evaporated under vacuum to give a crude product which was crystallised from ethyl acetate/hexane to afford the title compound (0.476 g, 37%), m.p. 116-119° C. Found: C, 67.00; H, 6.21; N, 17.23. C18H20N4O2 requires C, 66.65; H, 6.21; N, 17.27%.

Workup

  1. temperaturewas refluxed for 5 hours
  2. temperatureAfter cooling
  3. extractionthe solution was exhaustively extracted with ethyl acetate
  4. washThe combined extracts were washed with brine (30 ml)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent evaporated under vacuum
  8. customto give a crude product which
  9. customwas crystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-176fa206817341b68b024e266c2691ac
Source dataset
uspto-grants-2001_03
Patent number
US06200980B1

Reaction notes

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