Sodium Hydroxide → (E)-3-(3-Methyl-4-oxo-1-n-propyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-6-yl)-4-n-propoxycinnamic acid

HRID 1532070Notes

Reaction equation

HRID 1532070 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[C:29]([CH3:30])=[N:28][N:27]([CH2:31][CH2:32][CH3:33])[C:25]=3[N:26]=2)[CH:12]=1)(C)(C)C>CO>[CH3:30][C: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[N:27]([CH2:31][CH2:32][CH3:33])[N:28]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 135450039(E)-3-(3-methyl-4-oxo-1-n-propyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-6-yl)-4-n-propoxycinnamic acid t-butyl ester

Product 1

HCID 135448235(E)-3-(3-Methyl-4-oxo-1-n-propyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-6-yl)-4-n-propoxycinnamic acidYield 12%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2N Aqueous sodium hydroxide solution (8.0 ml, 0.016 mol) was added to a solution of (E)-3-(3-methyl-4-oxo-1-n-propyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-6-yl)-4-n-propoxycinnamic acid t-butyl ester (Example 12; 1.8 g, 0.004 mol) in methanol (8 ml) and the mixture heated under reflux for 5 hours. The methanol was removed by evaporation under vacuum and the aqueous solution acidified to pH 1 with 2N hydrochloric acid. Exhaustive extraction of the product with 10% methanol in ethyl acetate was followed by drying of the combined extracts (Na2SO4) and evaporation of solvents under vacuum to furnish an off-white solid. Crystallisation from ethyl acetate-methanol afforded the title compound as white crystals (0.18 g, 12%), m.p. 231-232° C. Found: C, 63.52; H, 5.96; N, 14.00. C21H24N4O4 requires C, 63.62; H, 6.10; N, 14.13%.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 5 hours
  3. customThe methanol was removed by evaporation under vacuum
  4. extractionExhaustive extraction of the product with 10% methanol in ethyl acetate
  5. dry with materialby drying of the combined extracts (Na2SO4) and evaporation of solvents under vacuum
  6. customto furnish an off-white solid
  7. customCrystallisation from ethyl acetate-methanol

Sources & evidence

ORD record
ord-7b1c883b49d048bbba0335c63e50df6f
Source dataset
uspto-grants-2001_03
Patent number
US06200980B1

Reaction notes

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