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N,N-Dimethylacrylamide → (E)-4-Ethoxy-3-(1-methyl-7-oxo-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-5-yl)cinnamic acid dimethylamide

HRID 21931
Notes
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Reaction equation

HRID 21931 reaction equation
[CH3:1][N:2]([CH3:7])[C:3](=[O:6])[CH:4]=[CH2:5].Br[C:9]1[CH:10]=[CH:11][C:12]([O:29][CH2:30][CH3:31])=[C:13]([C:15]2[NH:16][C:17](=[O:28])[C:18]3[N:23]([CH3:24])[N:22]=[C:21]([CH2:25][CH2:26][CH3:27])[C:19]=3[N:20]=2)[CH:14]=1>>[CH3:1][N:2]([CH3:7])[C:3](=[O:6])/[CH:4]=[CH:5]/[C:9]1[CH:10]=[CH:11][C:12]([O:29][CH2:30][CH3:31])=[C:13]([C:15]2[NH:16][C:17](=[O:28])[C:18]3[N:23]([CH3:24])[N:22]=[C:21]([CH2:25][CH2:26][CH3:27])[C:19]=3[N:20]=2)[CH:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 17587N,N-DimethylacrylamideHCID 1357385545-(5-Bromo-2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-D]pyrimidin-7(6H)-one

Product 1

HCID 136401237(E)-4-Ethoxy-3-(1-methyl-7-oxo-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-5-yl)cinnamic acid dimethylamide

Procedure

The title compound was prepared from N,N-dimethylacrylamide 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, following crystallisation from ethyl acetate-hexane, as colourless crystals (38%), m.p. 219°-221° C. Found: C,64.15; H,6.46; N,16.96. C22H27N5O3 requires C,64.53; H,6.65; N,17.10%.

Workup

  • customwas obtained
  • customcrystallisation from ethyl acetate-hexane
  • Sources & evidence

    ORD record
    ord-a2be3b7853fd422ea0419f6f2130e228
    Source dataset
    uspto-grants-1995_06
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US05426107

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes