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

HRID 2056249Notes

Reaction equation

HRID 2056249 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

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)+)]

Workup

  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)

Sources & evidence

ORD record
ord-ab11025c73d6429a819fa33ba019d7d0
Source dataset
uspto-grants-2008_02
Patent number
US07335654B2

Reaction notes

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