(R)-8-cyclopentyl-2-(2-(3,6-dihydro-2H-pyran-4-yl)-1H-imidazol-1-yl)-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one → HCID 58405709, compound

HRID 44850Notes

Reaction equation

HRID 44850 reaction equation
[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([N:16]4[CH:20]=[CH:19][N:18]=[C:17]4[C:21]4[CH2:22][CH2:23][O:24][CH2:25][CH:26]=4)[N:12]=[CH:11][C:10]=3[N:9]([CH3:27])[C:8](=[O:28])[C@H:7]2[CH2:29][CH3:30])[CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([N:16]4[CH:20]=[CH:19][N:18]=[C:17]4[CH:21]4[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)[N:12]=[CH:11][C:10]=3[N:9]([CH3:27])[C:8](=[O:28])[C@H:7]2[CH2:29][CH3:30])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 58405609(R)-8-cyclopentyl-2-(2-(3,6-dihydro-2H-pyran-4-yl)-1H-imidazol-1-yl)-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one

Product 1

HCID 58405709HCID 58405709, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(R)-8-cyclopentyl-2-(2-(3,6-dihydro-2H-pyran-4-yl)-1H-imidazol-1-yl)-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one (Example 84, 34 mg) in 5 mL of MeOH, Pd/C (20 mg) was added. This reaction mixture was placed under a hydrogen balloon until all the starting material was consumed. The resulting mixture was filtered through a plug of Celite, and the plug was washed several times with EtOAc. The mixture was concentrated under reduced pressure and further purified by preparative HPLC. LCMS: 411.2 m/z (M+H)+; ret. Time: 6.45 min (Analytical Method C).

Workup

  1. customwas consumed
  2. filtrationThe resulting mixture was filtered through a plug of Celite
  3. washthe plug was washed several times with EtOAc
  4. concentrationThe mixture was concentrated under reduced pressure
  5. customfurther purified by preparative HPLC

Sources & evidence

ORD record
ord-e364498091d940a7ba82f6947c5e6526
Source dataset
uspto-grants-2013_09
Patent number
US08541418B2

Reaction notes

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