Nitrodenafil → 5-(5-Amino-2-ethoxyphenyl)-1-methyl-3-propyl-1,4-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

HRID 1532139Notes

Reaction equation

HRID 1532139 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:5]=1[C:13]1[NH:14][C:15](=[O:26])[C:16]2[N:21]([CH3:22])[N:20]=[C:19]([CH2:23][CH2:24][CH3:25])[C:17]=2[N:18]=1)[CH3:2]>C(O)C.[Pd]>[NH2:10][C:7]1[CH:8]=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[C:5]([C:13]2[NH:14][C:15](=[O:26])[C:16]3[N:21]([CH3:22])[N:20]=[C:19]([CH2:23][CH2:24][CH3:25])[C:17]=3[N:18]=2)[CH:6]=1

Participants

4

Reactant 1

HCID 135566056Nitrodenafil

Product 1

HCID 1357385605-(5-Amino-2-ethoxyphenyl)-1-methyl-3-propyl-1,4-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-oneYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-(2-Ethoxy-5-nitrophenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (0.64 g, 0.0018 mol) was dissolved in ethanol (50 ml) and the solution stirred with 5% palladium on charcoal catalyst (0.050 g) under hydrogen at room temperature and 50 p.s.i. pressure for 4 hours. The mixture was filtered to remove the catalyst, the filtrate evaporated under vacuum, and the residue triturated with ether to give the title compound as an off-white solid (0.56 g, 95%), m.p. 147-148° C. Found: C,62.63; H,6.60; N,21.57. C17H21N5O2 requires C,62.36; H,6.47; N, 21.39%.

Workup

  1. filtrationThe mixture was filtered
  2. customto remove the catalyst
  3. customthe filtrate evaporated under vacuum
  4. customthe residue triturated with ether

Sources & evidence

ORD record
ord-d104420209404f6e9aaf846860f8ec51
Source dataset
uspto-grants-2001_03
Patent number
US06200980B1

Reaction notes

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