Acetic Acid → 5-[5-(3-Aminopropyl)-2-ethoxyphenyl]-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one

HRID 327049Notes

Reaction equation

HRID 327049 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][CH2:16][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:29])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:29])[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 2

HCID 176Acetic AcidHCID 178440314(E)-4-Ethoxy-3-(1-methyl-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 38%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A solution of (E)-4-ethoxy-3-(-1-methyl-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 evaported under vacuum to give a brown solid, crystallisation 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. customto give
  8. customa brown solid, crystallisation of which from hexane-ethyl acetate

Sources & evidence

ORD record
ord-3f58702d637e41729c5744100d0cae26
Source dataset
uspto-grants-1993_12
Patent number
US05272147

Reaction notes

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