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

HRID 21938
Notes
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Reaction equation

HRID 21938 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.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.CCCCCC>CC(=O)CC>[CH3:18][N:17]1[C:12]2[C:11](=[O:22])[NH:10][C:9]([C:7]3[CH:8]=[C:3]([CH2:2][N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8058HexaneHCID 8083MorpholineHCID 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 1361601131-Methyl-5-(5-morpholinomethyl-2-n-propoxyphenyl)-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-oneYield 53%

Reagents, catalysts & solvents 1

HCID 6569
Methyl Ethyl Ketone
Solvent
2×

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 (Preparation 16, 0.60 g, 0.0016 mol) in 2-butanone (10 ml) was added dropwise to a stirred solution of morpholine (0.42 g, 0.0048 mol) in 2-butanone (40 ml) at 0° C. The solution was then heated under reflux for 16 hours, cooled and evaporated under vacuum. The residue was suspended in water (50 ml) and the suspension extracted with ethyl acetate (3×20 ml). The organic extracts were combined, washed with brine (2×30 ml), dried (Na2SO4) and evaporated under vacuum. The residue was chromatographed on silica gel (12 g), using an elution gradient of methanol in dichloromethane (0-2% methanol), to give an oil which solidified on trituration with hexane. Crystallisation from ethyl acetate-hexane gave the title compound as a colourless solid (0.36 g, 53%), m.p. 106°-107° C. Found: C,64.76; H,7.34; N,16.36. C23H31N5O3 requires C,64.92; H,7.34; N,16.46%.

Workup

  1. temperatureThe solution was then heated
  2. temperatureunder reflux for 16 hours
  3. temperaturecooled
  4. customevaporated under vacuum
  5. extractionthe suspension extracted with ethyl acetate (3×20 ml)
  6. washwashed with brine (2×30 ml)
  7. dry with materialdried (Na2SO4)
  8. customevaporated under vacuum
  9. customThe residue was chromatographed on silica gel (12 g)
  10. customto give an oil which
  11. customCrystallisation from ethyl acetate-hexane

Sources & evidence

ORD record
ord-acd8c3bb96e44a78a59fe51dd73884c8
Source dataset
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05426107

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes