Ethanol → 5-(5-Ethoxymethyl-2-n-propoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one
Reaction equation
[Na].Cl[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:24][CH2:25][CH2:26][CH3:27])=[C:8]([C:10]2[NH:11][C:12](=[O:23])[C:13]3[N:18]([CH3:19])[N:17]=[C:16]([CH2:20][CH2:21][CH3:22])[C:14]=3[N:15]=2)[CH:9]=1.[CH2:28]([OH:30])[CH3:29]>>[CH2:28]([O:30][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:24][CH2:25][CH2:26][CH3:27])=[C:8]([C:10]2[NH:11][C:12](=[O:23])[C:13]3[N:18]([CH3:19])[N:17]=[C:16]([CH2:20][CH2:21][CH3:22])[C:14]=3[N:15]=2)[CH:9]=1)[CH3:29]Participants
Procedure
Sodium (0.15 g, 0.0013 mol) was added portionwise to ethanol (40 ml) over 1 hour. 5-(5-Chloromethyl-2-n-propoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (0.5 g, 0.0013 mol) was then added to the solution and, after 3 days at room temperature, the solvent was removed by evaporation under vacuum. The residual solid was suspended in water (50 ml) and the suspension extracted with ethyl acetate (3×30 ml). The extracts were then combined, dried (Na2SO4) and evaporated under vacuum to give a green solid. Chromatography on silica gel (6 g) using a methanol in dichloromethane elution gradient gave, after crystallisation of the required product from a hexane-ethyl acetate mixture, the title compound as a white solid (0.2 g, 39%) m.p. 89°-90° C. Found: C,65.87; H,7.57; N,14.66. C21H28N4O3 requires C,65.60; H,7.34; N,14.57%.
Workup
- customthe solvent was removed by evaporation under vacuum
- extractionthe suspension extracted with ethyl acetate (3×30 ml)
- dry with materialdried (Na2SO4)
- customevaporated under vacuum
- customto give a green solid
- washa methanol in dichloromethane elution gradient
- customgave
- customafter crystallisation of the required product from a hexane-ethyl acetate mixture
Sources & evidence
- ORD record
- ord-12cbdc745c9b4344b6925bda64e87255
- Source dataset
- uspto-grants-1995_06
- Patent number
- US05426107
Reaction notes
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