HCID 66743611, compound → HCID 66744221, compound

HRID 2364068Notes

Reaction equation

HRID 2364068 reaction equation
[CH3:1][C:2]1([CH3:28])[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[CH:10]=2)[C:6]2[CH:18]=[C:19]([C:21]3[CH:22]=[N:23][NH:24][C:25]=3[CH3:26])[S:20][C:5]=2[C:4](=[O:27])[NH:3]1>[Pt](=O)=O.C(O)C>[NH2:15][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[CH2:8][N:7]1[C:6]2[CH:18]=[C:19]([C:21]3[CH:22]=[N:23][NH:24][C:25]=3[CH3:26])[S:20][C:5]=2[C:4](=[O:27])[NH:3][C:2]1([CH3:28])[CH3:1]

Participants

4

Reactant 1

HCID 66743611HCID 66743611, compound

Product 1

HCID 66744221HCID 66744221, compoundYield 38.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2,2-dimethyl-6-(5-methyl-1H-pyrazol-4-yl)-1-(3-nitrobenzyl)-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one (147 mg, 0.37 mmol), platinum(IV) oxide (15 mg) and ethanol (20 mL) was stirred at room temperature for 3 h under hydrogen atmosphere (1 atm). Then, the catalyst was removed by filtration. After removal of the solvent at reduced pressure, the residue was purified by column chromatography (Purif, silica gel, EtOAc to 90:10 EtOAc/MeOH), then crystallized from MeOH/EtOAc/hexane to give the title compound (52 mg, 38%) as a yellow solid:

Workup

  1. customThen, the catalyst was removed by filtration
  2. customAfter removal of the solvent at reduced pressure
  3. customthe residue was purified by column chromatography (Purif, silica gel, EtOAc to 90:10 EtOAc/MeOH)
  4. customcrystallized from MeOH/EtOAc/hexane

Sources & evidence

ORD record
ord-0ad3e43b558a47c09beff96c8e3ef502
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

Loading…