9-((3aR,4R,6R,6aR)-6-(((3-(azidomethyl)cyclobutyl)(methyl)amino)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-amine → 9-((3aR,4R,6R,6aR)-6-(((3-(aminomethyl)cyclobutyl)(methyl)amino)methyl)-2,2-dimethyltetrahydro furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-amine

HRID 511585Notes

Reaction equation

HRID 511585 reaction equation
[N:1]([CH2:4][CH:5]1[CH2:8][CH:7]([N:9]([CH2:11][C@@H:12]2[C@H:16]3[O:17][C:18]([CH3:21])([CH3:20])[O:19][C@H:15]3[C@H:14]([N:22]3[CH:30]=[N:29][C:28]4[C:23]3=[N:24][CH:25]=[N:26][C:27]=4[NH2:31])[O:13]2)[CH3:10])[CH2:6]1)=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][CH:5]1[CH2:6][CH:7]([N:9]([CH2:11][C@@H:12]2[C@H:16]3[O:17][C:18]([CH3:21])([CH3:20])[O:19][C@H:15]3[C@H:14]([N:22]3[CH:30]=[N:29][C:28]4[C:23]3=[N:24][CH:25]=[N:26][C:27]=4[NH2:31])[O:13]2)[CH3:10])[CH2:8]1

Participants

4

Reactant 1

HCID 866661089-((3aR,4R,6R,6aR)-6-(((3-(azidomethyl)cyclobutyl)(methyl)amino)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-amine

Product 1

HCID 677761929-((3aR,4R,6R,6aR)-6-(((3-(aminomethyl)cyclobutyl)(methyl)amino)methyl)-2,2-dimethyltetrahydro furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd/C (10 mg) was added to a solution of 9-((3aR,4R,6R,6aR)-6-(((3-(azidomethyl)cyclobutyl)(methyl)amino)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-amine (90 mg, 0.21 mmol) in MeOH (6 ml). The mixture was stirred at RT overnight under an atmosphere of H2. The mixture was filtered and the filtrate was concentrated to obtain the title compound which was used directly in the next step.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-bc585bb9fa104fa08843d18a5354cc88
Source dataset
uspto-grants-2015_08
Patent number
US09096634B2

Reaction notes

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