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

HRID 327055Notes

Reaction equation

HRID 327055 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>C(OCC)(=O)C.[Pd]>[CH3:18][N:17]1[C:12]2[C:11](=[O:22])[NH:10][C:9]([C:7]3[CH:8]=[C:3]([CH3:2])[CH:4]=[CH:5][C:6]=3[O:23][CH2:24][CH2:25][CH3:26])=[N:14][C:13]=2[C:15]([CH2:19][CH2:20][CH3:21])=[N:16]1

Participants

4

Reactant 1

HCID 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 1355439961-Methyl-5-(5-methyl-2-n-propoxyphenyl)-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-oneYield 27.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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 ethyl acetate (50 ml) was stirred with 10% palladium on charcoal catalyst under a hydrogen atmosphere at 50 p.s.i. and room temperature. After 1 hour, the mixture was filtered and the filtrate evaported under vacuum to give a pale green solid. Chromatography on silica gel (4 g) using a methanol in dichloromethane elution gradient gave a white solid, crystallisation of which from hexane-ethyl acetate gave the title compound as colourless needles (0.12 g, 26%), m.p. 115°-116° C. Found D,66.66; H,7.12; N,16.55. C19H24N4O2 requires C,67.04; H,7.11; N,16.46%

Workup

  1. customroom temperature
  2. filtrationthe mixture was filtered
  3. customto give a pale green solid
  4. washa methanol in dichloromethane elution gradient
  5. customgave
  6. customa white solid, crystallisation of which from hexane-ethyl acetate

Sources & evidence

ORD record
ord-5d70fb991a564e288f0989929bd79641
Source dataset
uspto-grants-1993_12
Patent number
US05272147

Reaction notes

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