6-[4-(2-Butoxy-vinyl)-phenyl]-5-(4-chloro-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one → 6-[4-(2-Butoxyethyl)-phenyl]-5-(4-chloro-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

HRID 1693562Notes

Reaction equation

HRID 1693562 reaction equation
[CH2:1]([O:5][CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)[C:16](=[O:29])[C:17]3[CH:22]=[N:21][N:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:18]=3[N:19]=2)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH3:4]>CCO.[Pd]>[CH2:1]([O:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[N:15]([C:30]3[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=3)[C:16](=[O:29])[C:17]3[CH:22]=[N:21][N:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:18]=3[N:19]=2)=[CH:12][CH:13]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 672814696-[4-(2-Butoxy-vinyl)-phenyl]-5-(4-chloro-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

Product 1

HCID 578980226-[4-(2-Butoxyethyl)-phenyl]-5-(4-chloro-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-oneYield 70.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 6-[4-(2-butoxy-vinyl)-phenyl]-5-(4-chloro-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one (5 mg, 0.01 mmol) in EtOH (1 mL) is added Pd/C (2 mg). The system is degassed by alternately applying vacuum and H2 for 3 times. The mixture is then stirred at room temperature under H2 for 24 h. After removing the catalyst by filtration, the filtrate is concentrated and purified by flash column chromatography (silica gel, 0˜30% EtOAc/hexane) to provide the title compound as white solid (3.5 mg, 69%). HPLC-MS calculated C29H25ClN4O2 (M+1+): 497.2. Found: 497.2

Workup

  1. customThe system is degassed
  2. customAfter removing the catalyst
  3. filtrationby filtration
  4. concentrationthe filtrate is concentrated
  5. custompurified by flash column chromatography (silica gel, 0˜30% EtOAc/hexane)

Sources & evidence

ORD record
ord-de6936af252949f9b6c5abbce84fd2da
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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