HCID 18362931, compound → HCID 18362947, compound

HRID 1003367Notes

Reaction equation

HRID 1003367 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]#[C:6][C:7]1[N:8]([CH2:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=[CH:26][CH:25]=2)[CH:9]=[C:10]2[C:15]=1[C:14](=[O:16])[N:13]([CH3:17])[C:12](=[O:18])[N:11]2[CH2:19][CH:20]([CH3:22])[CH3:21].[H][H]>C(O)C.[Pd]>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[N:8]([CH2:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=[CH:26][CH:25]=2)[CH:9]=[C:10]2[C:15]=1[C:14](=[O:16])[N:13]([CH3:17])[C:12](=[O:18])[N:11]2[CH2:19][CH:20]([CH3:22])[CH3:21]

Participants

5

Reactant 2

HCID 18362931HCID 18362931, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 18362947HCID 18362947, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

The compound of Example 13, 5-(5-hydroxypent-1-ynyl)-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (75 mg) was suspended in ethanol (50 ml). A suspension of 10% palladium on carbon (7 mg) in ethanol (3 ml) was added and the mixture was hydrogenated. When hydrogen uptake ceased, the reaction mixture was filtered and the solvent was removed by rotary evaporation. The crude product was purified by chromatography on silica eluting with ethyl acetate:isohexane (3:1) to give the title compound (29 mg) as an oil.

Workup

  1. additionwas added
  2. filtrationthe reaction mixture was filtered
  3. customthe solvent was removed by rotary evaporation
  4. customThe crude product was purified by chromatography on silica eluting with ethyl acetate:isohexane (3:1)

Sources & evidence

ORD record
ord-eff2957b6cf1497c81073d81426361b4
Source dataset
uspto-grants-2000_04
Patent number
US06046204

Reaction notes

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