Ethylene Glycol → 5-(5-Hydroxymethyl-2-n-propoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one

HRID 327056Notes

Reaction equation

HRID 327056 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:23][CH2:24][CH2:25][CH3:26])=[C:7]([C:9]2[NH:10][C:11](=[O:22])[C:12]3[N:17]([CH3:18])[N:16]=[C:15]([CH2:19][CH2:20][CH3:21])[C:13]=3[N:14]=2)[CH:8]=1.[OH-].[Na+].C(O)C[OH:31].O>CS(C)=O>[OH:31][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:23][CH2:24][CH2:25][CH3:26])=[C:7]([C:9]2[NH:10][C:11](=[O:22])[C:12]3[N:17]([CH3:18])[N:16]=[C:15]([CH2:19][CH2:20][CH3:21])[C:13]=3[N:14]=2)[CH:8]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 14798Sodium HydroxideHCID 1361162095-(5-Chloromethyl-2-n-propoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo-[4,3-d]pyrimidin-7-one

Product 1

HCID 1360140445-(5-Hydroxymethyl-2-n-propoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-oneYield 2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 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) in dimethyl sulphoxide (10 ml) was added sodium hydroxide (0.26 g, 0.0065 mol) and ethylene glycol (0.41 g, 0.0065 mol). The reaction mixture was heated at 100° C. for 6 hours, allowed to cool and poured into water (50 ml), then the aqueous mixture extracted with ethyl acetate (3>30 ml). The combined extracts were filtered, dried (Na2SO4) and evaporated under vacuum to provide an oil which was purified by chromatography on silica gel (6g), using a methanol in dichloromethane elution gradient (0-3%) methanol). The solid product was crystallised from hexane-ethyl acetate to afford the title compound as a white solid (2%), m.p. 174°-175° C. Found: C,63.97; H,6.66; N,15.57. C19H24N4O3 requires C,64.03; H,6.79; N,15.72%.

Workup

  1. temperatureto cool
  2. extractionthe aqueous mixture extracted with ethyl acetate (3>30 ml)
  3. filtrationThe combined extracts were filtered
  4. dry with materialdried (Na2SO4)
  5. customevaporated under vacuum
  6. customto provide an oil which
  7. customwas purified by chromatography on silica gel (6g)
  8. washa methanol in dichloromethane elution gradient (0-3%) methanol)
  9. customThe solid product was crystallised from hexane-ethyl acetate

Sources & evidence

ORD record
ord-b4cd32489adb4fe7aa8bcad5ebde37da
Source dataset
uspto-grants-1993_12
Patent number
US05272147

Reaction notes

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