Morpholine → HCID 135738544, compound

HRID 1532063Notes

Reaction equation

HRID 1532063 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Br[CH2:8][C:9]([C:11]1[CH:12]=[CH:13][C:14]([O:30][CH2:31][CH3:32])=[C:15]([C:17]2[NH:18][C:19](=[O:29])[C:20]3[CH:25]=[N:24][N:23]([CH2:26][CH2:27][CH3:28])[C:21]=3[N:22]=2)[CH:16]=1)=[O:10].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:31]([O:30][C:14]1[CH:13]=[CH:12][C:11]([C:9](=[O:10])[CH2:8][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:16][C:15]=1[C:17]1[NH:18][C:19](=[O:29])[C:20]2[CH:25]=[N:24][N:23]([CH2:26][CH2:27][CH3:28])[C:21]=2[N:22]=1)[CH3:32]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 135738551HCID 135738551, compound

Product 1

HCID 135738544HCID 135738544, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Morpholine (0.175 g, 0.002 mol) was added to a stirred suspension of 6-(5-bromoacetyl-2-ethoxyphenyl)-1-n-propyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (Preparation 4; 0.70 g, 0.0017 mol) and anhydrous potassium carbonate (0.461 g, 0.0033 mol) in acetonitrile (30 ml) and the resulting mixture stirred at room temperature for 3 hours. The solvent was removed by evaporation under vacuum, the residue partitioned between water (20 ml) and dichloromethane (30 ml), the organic phase removed and the aqueous phase extracted with dichloromethane (3×30 ml). The combined organic solutions were dried (Na2SO4) and the solvent removed by evaporation under vacuum to give a yellow oil. Purification by column chromatography (SiO2, 5% MeOH in CH2Cl2), followed by crystallisation from ethyl acetate-hexane, provided the title compound as white crystals (0.62 g, 85%), m.p. 160-162° C. Found: C,61.96; H,6.29; N,16.32. C22H27N5O4 requires C,62.10; H,6.40; N,16.46%.

Workup

  1. customThe solvent was removed by evaporation under vacuum
  2. customthe residue partitioned between water (20 ml) and dichloromethane (30 ml)
  3. customthe organic phase removed
  4. extractionthe aqueous phase extracted with dichloromethane (3×30 ml)
  5. dry with materialThe combined organic solutions were dried (Na2SO4)
  6. customthe solvent removed by evaporation under vacuum
  7. customto give a yellow oil
  8. customPurification by column chromatography (SiO2, 5% MeOH in CH2Cl2)
  9. customfollowed by crystallisation from ethyl acetate-hexane

Sources & evidence

ORD record
ord-849345a15a91451e97b6d18468f1eb6c
Source dataset
uspto-grants-2001_03
Patent number
US06200980B1

Reaction notes

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