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

HRID 2056249노트

반응식

HRID 2056249 반응식
[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]

참가 물질

6

반응물 3

HCID 887MethanolHCID 104309696-Ethyl-9-(4-benzyloxyphenyl)-2-trifluoromethylpurineHCID 178418361HCID 178418361, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 176Acetic Acid용매

실험 절차

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)+)]

후처리

  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)

출처 및 근거

ORD 기록
ord-ab11025c73d6429a819fa33ba019d7d0
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07335654B2

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