HCID 90402931, compound → HCID 90402886, compound

HRID 2200718Notes

Reaction equation

HRID 2200718 reaction equation
C([O:8][CH:9]1[CH2:12][CH:11]([N:13]2[C:21](=[O:22])[C:20]3[N:19]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=4)[C:18]([O:31][C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([O:38][C:39]([F:42])([F:41])[F:40])[CH:33]=4)=[N:17][C:16]=3[N:15]([CH3:43])[C:14]2=[O:44])[CH2:10]1)C1C=CC=CC=1>CO.[Pd]>[Cl:30][C:27]1[CH:26]=[CH:25][C:24]([CH2:23][N:19]2[C:20]3[C:21](=[O:22])[N:13]([CH:11]4[CH2:10][CH:9]([OH:8])[CH2:12]4)[C:14](=[O:44])[N:15]([CH3:43])[C:16]=3[N:17]=[C:18]2[O:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([O:38][C:39]([F:42])([F:40])[F:41])[CH:33]=2)=[CH:29][CH:28]=1

Participants

4

Reactant 1

HCID 90402931HCID 90402931, compound

Product 1

HCID 90402886HCID 90402886, compoundYield 17.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-(3-(benzyloxy)cyclobutyl)-7-(4-chlorobenzyl)-3-methyl-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione (110 mg, 0.175 mmol) in methanol was added 5% Pd/C (15 mg). The mixture was hydrogenated at 45 psi for 30 min. The reaction was filtered and concentrated to give a crude product which was purified via preparative HPLC to give 7-(4-chlorobenzyl)-1-(3-hydroxycyclobutyl)-3-methyl-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione (11 mg, 17.7% yield) as white solid.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. customto give a crude product which
  4. customwas purified via preparative HPLC

Sources & evidence

ORD record
ord-f7d850c504704a22b5b2db4e90992630
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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