Sodium ethoxide → HCID 178440268, compound

HRID 1860563Notes

Reaction equation

HRID 1860563 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([Cl:14])=[CH:9][C:8]=2[Cl:15])[N:5]=[C:4]([CH:16]([CH3:18])[CH3:17])[C:3]=1[C:19]([NH2:21])=[O:20].[OH:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31](OCC)=O)=[CH:26][CH:25]=1.[O-]CC.[Na+]>C(O)C>[Cl:13][C:12]1[CH:11]=[C:10]([Cl:14])[CH:9]=[C:8]([Cl:15])[C:7]=1[N:6]1[C:2]2=[N:1][C:31]([CH2:30][C:27]3[CH:28]=[CH:29][C:24]([CH2:23][OH:22])=[CH:25][CH:26]=3)=[N:21][C:19](=[O:20])[C:3]2=[C:4]([CH:16]([CH3:18])[CH3:17])[NH:5]1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 14197000Ethyl 2-(4-(hydroxymethyl)phenyl)acetateHCID 185406305-Amino-3-isopropyl-1-(2,4,6-trichlorophenyl)pyrazole-4-carboxamide

Product 1

HCID 178440268HCID 178440268, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred solution of 347 mg (1.0 mmol) of 5-amino-3-isopropyl-1-(2,4,6-trichlorophenyl)pyrazole-4-carboxamide in 6 mL of absolute ethanol was added 777 mg (4.0 mmol) of ethyl 4-(hydroxymethyl)phenylacetate followed by 2.0 mL (5.33 mmol) of 2.66 M sodium ethoxide in ethanol. The solution was stirred 18 h at reflux, and the heating mantle was then removed. The reaction was treated with 25 mL of 5% aq. HOAc, cooled to ambient temperature, and extracted with EtOAc. The organic extract was washed twice with water and once with brine, dried (MgSO4), and chromatographed on silica gel (elution with 1:1 EtOAc-hexanes) to give, after removal of solvent, 320 mg (67%) of 1-(2,4,6-trichlorophenyl)-3-isopropyl-6-(4-(hydroxymethyl)benzyl)pyrazolo[3,4-d]pyrimidin-4-one as a white, amorphous solid. 1H NMR (300 MHz, CDCl3) d 11.46(br. s, 1H); 7.54(s, 2H); 7.42(d, 2H, J=8.1 Hz); 7.31(d, 2H, J=8.5 Hz); 4.66(s, 2H); 4.00(s, 2H); 3.47(septet, 1H, J=7.0 Hz); 1.48(d, 6H, J=7.0 Hz).

Workup

  1. temperatureat reflux
  2. customthe heating mantle was then removed
  3. additionThe reaction was treated with 25 mL of 5% aq. HOAc
  4. extractionextracted with EtOAc
  5. extractionThe organic extract
  6. washwas washed twice with water and once with brine
  7. dry with materialdried (MgSO4)
  8. customchromatographed on silica gel (elution with 1:1 EtOAc-hexanes)
  9. customto give
  10. customafter removal of solvent, 320 mg (67%) of 1-(2,4,6-trichlorophenyl)-3-isopropyl-6-(4-(hydroxymethyl)benzyl)pyrazolo[3,4-d]pyrimidin-4-one as a white, amorphous solid

Sources & evidence

ORD record
ord-938f2a52f383441c8742eabb03a79505
Source dataset
uspto-grants-2003_03
Patent number
US06531477B1

Reaction notes

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