1-(2-(6-amino-8-(3-fluorophenyl)-9-methyl-9H-2-purinyl)-1-ethynyl)-1-cyclopentanol → HCID 22133828, compound

HRID 1369389Notes

Reaction equation

HRID 1369389 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([C:11]#[C:12][C:13]2([OH:18])[CH2:17][CH2:16][CH2:15][CH2:14]2)[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1)[N:6]2[CH3:19].[H][H]>CO.Cl.[Pd]>[NH2:1][C:2]1[N:10]=[C:9]([CH2:11][CH2:12][C:13]2([OH:18])[CH2:14][CH2:15][CH2:16][CH2:17]2)[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1)[N:6]2[CH3:19]

Participants

6

Reactant 2

HCID 98413641-(2-(6-amino-8-(3-fluorophenyl)-9-methyl-9H-2-purinyl)-1-ethynyl)-1-cyclopentanolHCID 178418361HCID 178418361, compound

Product 1

HCID 22133828HCID 22133828, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 300 mg of 1-[2-[6-amino-8-(3-fluorophenyl)-9-methyl-9H-2-purinyl]-1-ethynyl]-1-cyclopentanol in 20 ml of methanol were added six drops of 5N hydrochloric acid and 63 mg of 10% palladium/carbon and the mixture was stirred in a hydrogen atmosphere at room temperature for 17 hours. The palladium/carbon was filtered off, the filtrate was concentrated and the residue was dissolved in ethyl acetate and saturated sodium hydrogen carbonate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The resulting residue was subjected to a silica gel column chromatography (15 g of silica gel; dichloromethane, dichloromethane/methanol (40:1, 20:1 and 10:1) to give 1-[2-[6-amino-8-(3-fluorophenyl)-9-methyl-9H-2-purinyl]-1-ethyl]-1-cyclopentanol. This was dissolved in methanol and then five drops of 5N hydrochloric acid were added thereto followed by concentrating. Ether was added to the residue and the crystals were collected by filtration and washed with ether to give 6209 mg of the product. The yield was 69%.

Workup

  1. filtrationThe palladium/carbon was filtered off
  2. concentrationthe filtrate was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a14306568c034ae7aec0ffcad254b3d3
Source dataset
uspto-grants-2003_06
Patent number
US06579868B1

Reaction notes

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