N-[(E)-3-(3-Methyl-4-oxo-1-n-propyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-6-yl)-4-n-propoxy-cinnamoyl]morpholine → N-{3-[3-(3-Methyl-4-oxo-1-n-propyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-6-yl)-4-n-propoxyphenyl]-propanoyl}morpholine

HRID 1532072Notes

Reaction equation

HRID 1532072 reaction equation
[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][C:7]([C:12]3[CH:13]=[C:14]([CH:25]=[CH:26][C:27]=3[O:28][CH2:29][CH2:30][CH3:31])/[CH:15]=[CH:16]/[C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[O:18])=[N:6][C:5]=2[N:4]([CH2:32][CH2:33][CH3:34])[N:3]=1>C(O)C.[Pd]>[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][C:7]([C:12]3[CH:13]=[C:14]([CH2:15][CH2:16][C:17]([N:19]4[CH2:20][CH2:21][O:22][CH2:23][CH2:24]4)=[O:18])[CH:25]=[CH:26][C:27]=3[O:28][CH2:29][CH2:30][CH3:31])=[N:6][C:5]=2[N:4]([CH2:32][CH2:33][CH3:34])[N:3]=1

Participants

4

Reactant 1

HCID 135532857N-[(E)-3-(3-Methyl-4-oxo-1-n-propyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-6-yl)-4-n-propoxy-cinnamoyl]morpholine

Product 1

HCID 135453502N-{3-[3-(3-Methyl-4-oxo-1-n-propyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-6-yl)-4-n-propoxyphenyl]-propanoyl}morpholineYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of N-[(E)-3-(3-methyl-4-oxo-1-n-propyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-6-yl)-4-n-propoxycinnamoyl]morpholine (0.5 g, 0.0011 mol) in ethanol (30 ml) was stirred with 10% palladium on charcoal catalyst (0.05 g) under a hydrogen pressure of 50 p.s.i. (3.45 bar) at room temperature for 14 hours. The reaction mixture was filtered and solvent removed by evaporation under vacuum. Trituration of the residue with diethyl ether, followed by crystallisation from ethyl acetate-hexane, afforded the title compound as white crystals (0.37 g, 74%), m.p. 132-133° C. Found: C, 64.39; H, 7.26; N, 14.80. C25H33N5O4 requires C, 64.22; H, 7.11; N, 14.98%.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customsolvent removed by evaporation under vacuum
  3. customTrituration of the residue with diethyl ether, followed by crystallisation from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b30fcd3774e14f878d48834b67695762
Source dataset
uspto-grants-2001_03
Patent number
US06200980B1

Reaction notes

Loading…