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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 327049
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 327049
[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
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Komponenten

4

Edukt 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

Produkt 1

HCID 1357385735-[5-(3-Aminopropyl)-2-ethoxyphenyl]-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-oneAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 935NickelKatalysator

Versuchsvorschrift

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%.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-3f58702d637e41729c5744100d0cae26
Quelldatensatz
uspto-grants-1993_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05272147

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