Water → 3-[4-Ethoxy-3-(1-methyl-7-oxo-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-5-yl)phenyl]propanoic acid

HRID 21930Notes

Reaction equation

HRID 21930 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][C:17](=[O:28])[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][C:17](=[O:28])[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 135738561HCID 135738561, compound

Product 1

HCID 1354582223-[4-Ethoxy-3-(1-methyl-7-oxo-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-5-yl)phenyl]propanoic acidYield 54.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (E)-4-Ethoxy-3-(1-methyl-7-oxo-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,62.25; 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-ba0218a684c9487d928012932f116e86
Source dataset
uspto-grants-1995_06
Patent number
US05426107

Reaction notes

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