(E)-4-Ethoxy-3-(1-methyl-7-oxo-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-5-yl)cinnamonitrile → 5-[5-(3-Aminopropyl)-2-ethoxyphenyl]-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one

HRID 1532098Notes

Reaction equation

HRID 1532098 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][C:7](/[CH:8]=[CH:9]/[C:10]#[N:11])=[CH:6][C:5]=1[C:14]1[NH:15][C:16](=[O:27])[C:17]2[N:22]([CH3:23])[N:21]=[C:20]([CH2:24][CH2:25][CH3:26])[C:18]=2[N:19]=1)[CH3:2]>C(O)(=O)C.[Ni]>[NH2:11][CH2:10][CH2:9][CH2:8][C:7]1[CH:12]=[CH:13][C:4]([O:3][CH2:1][CH3:2])=[C:5]([C:14]2[NH:15][C:16](=[O:27])[C:17]3[N:22]([CH3:23])[N:21]=[C:20]([CH2:24][CH2:25][CH3:26])[C:18]=3[N:19]=2)[CH:6]=1

Participants

4

Reactant 1

HCID 135710986(E)-4-Ethoxy-3-(1-methyl-7-oxo-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-5-yl)cinnamonitrile

Product 1

HCID 1357385735-[5-(3-Aminopropyl)-2-ethoxyphenyl]-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-oneYield 40.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of (E)-4-ethoxy-3-(l-methyl-7-oxo-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-5-yl)cinnamonitrile (0.25 g, 0.00064 mol) in glacial acetic acid (25 ml) was stirred with Raney nickel catalyst (25 mg) under hydrogen at room temperature and at 50 p.s.i. for 3 hours. The resulting mixture was filtered and the filtrate evaporated under vacuum. The residue was partitioned between saturated aqueous sodium carbonate solution (50 ml) and dichloromethane (30 ml), the layers separated and the aqueous phase further extracted with dichloromethane (2×30 ml). The organic solutions were combined, dried (Na2SO4) and evaporated under vacuum to give a brown solid, crystallization of which from hexane-ethyl acetate gave the title compound as fawn crystals (96 mg, 38%), m.p. 115-117° C. Found C,65.29; H,7.35; N,18.66. C20H27N5O2 requires C,65.02; H,7.37; N,18.96%.

Workup

  1. filtrationThe resulting mixture was filtered
  2. customthe filtrate evaporated under vacuum
  3. customThe residue was partitioned between saturated aqueous sodium carbonate solution (50 ml) and dichloromethane (30 ml)
  4. customthe layers separated
  5. extractionthe aqueous phase further extracted with dichloromethane (2×30 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated under vacuum
  8. customto give
  9. customa brown solid, crystallization of which from hexane-ethyl acetate

Sources & evidence

ORD record
ord-81140af582fb42b388aa1e916d205d4d
Source dataset
uspto-grants-2001_03
Patent number
US06200980B1

Reaction notes

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