Sodium ethoxide → HCID 178440268、化合物

HRID 1860563ノート

反応式

HRID 1860563 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 178440268HCID 178440268、化合物

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-938f2a52f383441c8742eabb03a79505
出典データセット
uspto-grants-2003_03
特許番号
US06531477B1

反応ノート

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