Quinoline → HCID 58647268, compound

HRID 1369388Notes

Reaction equation

HRID 1369388 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([C:11]#[C:12][C:13]([CH3:16])([OH:15])[CH3:14])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=1)[N:6]2[CH2:17][CH3:18].N1C2C(=CC=CC=2)C=CC=1.[H][H]>CO.[Pd]>[NH2:1][C:2]1[N:10]=[C:9](/[CH:11]=[CH:12]\[C:13]([CH3:16])([OH:15])[CH3:14])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=1)[N:6]2[CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 7047QuinolineHCID 22133963HCID 22133963, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58647268HCID 58647268, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 200 mg of 4-[6-amino-9-ethyl-8-(3-fluorophenyl)-9H-2-purinyl]-2-methyl-3-butyn-2-ol in 20 ml of methanol were added 5 μl of quinoline and 20 mg of 10% palladium/barium carbonate and the mixture was stirred in a hydrogen atmosphere at room temperature for 10 minutes. The palladium/barium carbonate was filtered off and the filtrate was concentrated and then the resulting residue was subjected to a silica gel column chromatography (15 g of silica gel; dichloromethane-dichloromethane/methanol=60:1-40:1) to give (Z)-4-[6-amino-9-ethyl-8-(3-fluorophenyl)-9H-2-purinyl]-2-methyl-3-buten-2-ol. This was dissolved in methanol and five drops of 5N hydrochloric acid were added thereto followed by concentrating. Ethyl acetate and ether were added to the resulting residue and the crystals were collected by filtration and washed with ether to give 851 mg of the product. The yield was 26%.

Workup

  1. filtrationThe palladium/barium carbonate was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1b777aacab024944ad240ed2ba3dd467
Source dataset
uspto-grants-2003_06
Patent number
US06579868B1

Reaction notes

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