HCID 18362931, compound → HCID 86755958, compound

HRID 369471Notes

Reaction equation

HRID 369471 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)[N:13]([CH3:17])[C:12](=O)[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[CH2:14][N:13]([CH3:17])[CH2:12][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 86755958HCID 86755958, 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)-1 H-pyrrolo[3,4-d]pyrimidine-2,4(3 H,6 H)-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-529d2041a88f4c71952acf85c58c29a5
Source dataset
uspto-grants-2000_10
Patent number
US06136974

Reaction notes

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