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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 327049Generated: October 29, 2026

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

https://huagongshe.com/reaction/327049

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
Reactant(E)-4-Ethoxy-3-(1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-5-yl)cinnamonitrileHCID 178440314—
CatalystNickelHCID 935—
Product5-[5-(3-Aminopropyl)-2-ethoxyphenyl]-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-oneHCID 13573857338%

Reaction Steps

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%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05272147
Source datasetuspto-grants-1993_12
ORD IDord-3f58702d637e41729c5744100d0cae26
Source noteuspto-grants-1993_12