Sodium Hydroxide → HCID 136331509, compound

HRID 21928Notes

Reaction equation

HRID 21928 reaction equation
[OH-].[Na+].C([O:7][C:8](=[O:35])/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH3:20])=[C:13]([C:21]2[NH:22][C:23](=[O:34])[C:24]3[N:29]([CH3:30])[N:28]=[C:27]([CH2:31][CH2:32][CH3:33])[C:25]=3[N:26]=2)[CH:12]=1)(C)(C)C>CO>[CH3:30][N:29]1[C:24]2[C:23](=[O:34])[NH:22][C:21]([C:13]3[CH:12]=[C:11]([CH:16]=[CH:15][C:14]=3[O:17][CH2:18][CH2:19][CH3:20])/[CH:10]=[CH:9]/[C:8]([OH:35])=[O:7])=[N:26][C:25]=2[C:27]([CH2:31][CH2:32][CH3:33])=[N:28]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 136331508(E)-3-(1-Methyl-7-oxo-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-n-propoxycinnamic acid t-butyl ester

Product 1

HCID 136331509HCID 136331509, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2N Aqueous sodium hydroxide solution (2.28 ml, 0.0046 mol) was added to a solution of (E)-3-(1-methyl-7-oxo-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-n-propoxycinnamic acid t-butyl ester (0.40 g, 0.00088 mol) in methanol (2.3 ml) and the mixture was heated under reflux for 18 hours. The methanol was removed by evaporation under vacuum, the residue dissolved in water (25 ml), and the solution extracted with ethyl acetate (4×15 ml). The aqueous layer was separated, acidified to pH 1 with hydrochloric acid, and then extracted with a mixture of methanol and ethyl acetate (3:97, 4×20 ml). The organic extracts were combined, dried (Na2SO4) and evaporated under vacuum, then the residue crystallised from ethyl acetate to give the title compound as a white solid (0.27 g, 77%), m.p. 229°-230° C. Found: C,63.64; H,5.98; N,14.14. C21H25N4O4 requires C,63.46; H,6.34; N,14.10%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. customThe methanol was removed by evaporation under vacuum
  4. dissolutionthe residue dissolved in water (25 ml)
  5. extractionthe solution extracted with ethyl acetate (4×15 ml)
  6. customThe aqueous layer was separated
  7. extractionextracted with a mixture of methanol and ethyl acetate (3:97, 4×20 ml)
  8. dry with materialdried (Na2SO4)
  9. customevaporated under vacuum
  10. customthe residue crystallised from ethyl acetate

Sources & evidence

ORD record
ord-cc41139547884ba282811d79cfacd214
Source dataset
uspto-grants-1995_06
Patent number
US05426107

Reaction notes

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