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

HRID 327048Notes

Reaction equation

[C:1](#[N:4])[CH:2]=[CH2:3].Br[C:6]1[CH:7]=[CH:8][C:9]([O:26][CH2:27][CH3:28])=[C:10]([C:12]2[NH:13][C:14](=O)[C:15]3[N:20]([CH3:21])[N:19]=[C:18]([CH2:22][CH2:23][CH3:24])[C:16]=3[N:17]=2)[CH:11]=1>>[CH2:27]([O:26][C:9]1[CH:8]=[CH:7][C:6](/[CH:3]=[CH:2]/[C:1]#[N:4])=[CH:11][C:10]=1[C:12]1[NH:13][CH2:14][C:15]2[N:20]([CH3:21])[N:19]=[C:18]([CH2:22][CH2:23][CH3:24])[C:16]=2[N:17]=1)[CH3:28]

Participants

Reactant 2

HCID 7855Acrylonitrile

HCID 1357385545-(5-Bromo-2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-D]pyrimidin-7(6H)-one

Product 1

HCID 178440314(E)-4-Ethoxy-3-(1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-5-yl)cinnamonitrile

Procedure

The title compound was prepared from acrylonitrile and 5-(5-bromo-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one following the procedure of Example 19 and was obtained as off-white crystals (33%). Found C,65.99; H,5.52; N,19.07. C20H21N5O2 requires C,66.10; H,5.82; N,19.27%.

Sources & evidence

ORD record: ord-0ba345190734476e97edd072d4ec6200
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05272147

Reaction notes

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