Methanol → 6-Ethyl-9-(4-hydroxyphenyl)-2-trifluoromethylpurine

HRID 2056249ノート

反応式

HRID 2056249 の反応式
[CH2:1]([C:3]1[N:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[N:9]=[C:8]2[C:4]=1[N:5]=[CH:6][N:7]2[C:16]1[CH:21]=[CH:20][C:19]([O:22]CC2C=CC=CC=2)=[CH:18][CH:17]=1)[CH3:2].CO.[H][H]>[Pd].C(O)(=O)C>[CH2:1]([C:3]1[N:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[N:9]=[C:8]2[C:4]=1[N:5]=[CH:6][N:7]2[C:16]1[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=1)[CH3:2]

参加物

6

反応物 3

HCID 887MethanolHCID 104309696-Ethyl-9-(4-benzyloxyphenyl)-2-trifluoromethylpurineHCID 178418361HCID 178418361、化合物

生成物 1

HCID 103578946-Ethyl-9-(4-hydroxyphenyl)-2-trifluoromethylpurine収率 93%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 176Acetic Acid溶媒

実験手順

A mixture of 6-ethyl-9-(4-benzyloxyphenyl)-2-trifluoromethylpurine (0.1 mmol), palladium on active carbon (0.001 mol, methanol (50 mL) and acetic acid (3 mL) was shaken under 30 psi hydrogen. After 5 hours, the reaction mixture was filtered through celite and the filtrate was concentrated under vacuum. The resulting residue was dissolved in 30 mL of ethyl acetate and washed with 5% aqueous sodium bicarbonate (1×30 mL). Concentration and Chromatography (5% methanol in dichloromethane) gave 6-ethyl-9-(4-hydroxyphenyl)-2-trifluoromethylpurine (21 mg, 93%). 1H NMR (300 MHz, CDCl3) δ 8.37 (s, 1H), 7.45 (d, J=7.2 Hz, 2H), 6.96 (d, J=7.2 Hz, 2H), 3.29 (q, J=7.5 Hz, 2 H), 3.11 (s, 1H), 1.41 (t, J=7.5 Hz, 3H). [ESMS m/z (309.4 (M+H)+)]

後処理

  1. filtrationthe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under vacuum
  3. dissolutionThe resulting residue was dissolved in 30 mL of ethyl acetate
  4. washwashed with 5% aqueous sodium bicarbonate (1×30 mL)
  5. concentrationConcentration and Chromatography (5% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-ab11025c73d6429a819fa33ba019d7d0
出典データセット
uspto-grants-2008_02
特許番号
US07335654B2

反応ノート

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