Water → HCID 178440320, compound

HRID 327046Notes

Reaction equation

HRID 327046 reaction equation
[CH2:1]([O:3][C:4]1[CH:14]=[CH:13][C:7](/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11])=[CH:6][C:5]=1[C:15]1[NH:16][CH2:17][C:18]2[N:23]([CH3:24])[N:22]=[C:21]([CH2:25][CH2:26][CH3:27])[C:19]=2[N:20]=1)[CH3:2].C(OCC)(=O)C.O>CO.[Pd]>[CH2:1]([O:3][C:4]1[CH:14]=[CH:13][C:7]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:6][C:5]=1[C:15]1[NH:16][CH2:17][C:18]2[N:23]([CH3:24])[N:22]=[C:21]([CH2:25][CH2:26][CH3:27])[C:19]=2[N:20]=1)[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 178440318HCID 178440318, compound

Product 1

HCID 178440320HCID 178440320, compoundYield 56.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (E)-4-Ethoxy-3-(-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-5-yl)cinnamic acid (0.426 g, 0.0011 mol) in a mixture of methanol (28.5 ml), ethyl acetate (100 ml) and water (1.5 ml), was stirred with 5% palladium on charcoal catalyst (0.05 g) under a hydrogen atmosphere at room temperature and pressure for 3 hours. The catalyst was removed by filtration and the solvent removed by evaporation under vacuum. Crystallisation of the residue from ethyl acetate-hexane gave the title compound as beige crystals (0.23 g, 54%), m.p. 165°-167° C. Found C,62,24; H,6.17; N,14.09. C20H24N4O4 requires C,62.39; H,6.33; N,14.41%.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent removed by evaporation under vacuum
  3. customCrystallisation of the residue from ethyl acetate-hexane

Sources & evidence

ORD record
ord-3011c75ffa64427dbb88a05a650b5a61
Source dataset
uspto-grants-1993_12
Patent number
US05272147

Reaction notes

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