Dimethylamine → HCID 178440266, compound

HRID 1860560Notes

Reaction equation

HRID 1860560 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:14]2=[N:15][C:16]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=3)=[N:17][C:18](=[O:19])[C:13]2=[C:12]([CH:28]([CH3:30])[CH3:29])[NH:11]1.[CH2:31]=O.[CH3:33][NH:34][CH3:35].O>CC(O)=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:14]2=[N:15][C:16]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([CH2:33][N:34]([CH3:31])[CH3:35])=[C:23]([OH:27])[CH:22]=3)=[N:17][C:18](=[O:19])[C:13]2=[C:12]([CH:28]([CH3:30])[CH3:29])[NH:11]1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 712FormaldehydeHCID 962WaterHCID 178440267HCID 178440267, compound

Product 1

HCID 178440266HCID 178440266, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 464 mg (1.0 mmol) of 1-(2,4,6-trichlorophenyl)-3-isopropyl-6-(3-hydroxybenzyl)pyrazolo[3,4-d]pyrimidin-4-one in 10 mL of glacial HOAc was added 0.4 mL of 37% aq. formaldehyde followed by 0.5 mL of 40% aq. dimethylamine. The solution was stirred overnight at RT, and it was then heated to just below reflux for 20 min. The solution was poured into water and extracted with EtOAc. The organic extract was washed (brine), dried (MgSO4), and chromatographed on silica gel (elution with EtOAc) to afford, after removal of solvent, 135 mg (26%) of 1-(2,4,6-trichlorophenyl)-3-isopropyl-6-(4-(dimethylaminomethyl)-3-hydroxybenzyl)pyrazolo[3,4-d]pyrimidin-4-one as an off-white, amorphous solid. Mass spec. (ESI+): 520 (M+H)−.

Workup

  1. temperatureit was then heated to just
  2. temperaturebelow reflux for 20 min
  3. extractionextracted with EtOAc
  4. extractionThe organic extract
  5. washwas washed (brine)
  6. dry with materialdried (MgSO4)
  7. customchromatographed on silica gel (elution with EtOAc)
  8. customto afford
  9. customafter removal of solvent, 135 mg (26%) of 1-(2,4,6-trichlorophenyl)-3-isopropyl-6-(4-(dimethylaminomethyl)-3-hydroxybenzyl)pyrazolo[3,4-d]pyrimidin-4-one as an off-white, amorphous solid

Sources & evidence

ORD record
ord-2e2b12608f2c4cb3b71a5239ca3409d5
Source dataset
uspto-grants-2003_03
Patent number
US06531477B1

Reaction notes

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