8-azido-7-(4-chlorobenzyl)-3-methyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1H-purine-2,6(3H,7H)-dione → 8-amino-7-(4-chlorobenzyl)-3-methyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1H-purine-2,6(3H,7H)-dione

HRID 2200604Notes

Reaction equation

HRID 2200604 reaction equation
[N:1]([C:4]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[C:11]2[C:10](=[O:21])[N:9]([CH2:22][CH2:23][CH2:24][O:25][CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][O:27]3)[C:8](=[O:32])[N:7]([CH3:33])[C:6]=2[N:5]=1)=[N+]=[N-].[H][H]>C1COCC1.[Pd]>[NH2:1][C:4]1[N:12]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)[C:11]2[C:10](=[O:21])[N:9]([CH2:22][CH2:23][CH2:24][O:25][CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][O:27]3)[C:8](=[O:32])[N:7]([CH3:33])[C:6]=2[N:5]=1

Participants

5

Reactant 2

HCID 904030388-azido-7-(4-chlorobenzyl)-3-methyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1H-purine-2,6(3H,7H)-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 904031698-amino-7-(4-chlorobenzyl)-3-methyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1H-purine-2,6(3H,7H)-dioneYield 111.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

8-azido-7-(4-chlorobenzyl)-3-methyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1H-purine-2,6(3H,7H)-dione (0.19 g, 0.4 mmol) was dissolved in THF (5 mL) and 10% Pd/C (20 mg) was added. The reaction was blanketed in a hydrogen atmosphere (balloon) and stirred overnight at room temperature. The mixture was filtered through celite, the filter cake was washed with methanol. The filtrate was concentrated in vacuo to give a 8-amino-7-(4-chlorobenzyl)-3-methyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1H-purine-2,6(3H,7H)-dione (0.2 g, 100% yield) as a white solid. LCMS retention time 1.324 min; LCMS MH+-THP 364

Workup

  1. filtrationThe mixture was filtered through celite
  2. washthe filter cake was washed with methanol
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2e518c2ba15d442faa61d59a0f3c74bd
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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