Hydrochloric Acid → tert-butyl 3-(6-amino-8-oxo-7H-purin-9(8H)-yl)phenyl(methyl)carbamate

HRID 1887053Notes

Reaction equation

HRID 1887053 reaction equation
C([N:8](CC1C=CC=CC=1)[C:9]1[N:17]=[CH:16][N:15]=[C:14]2[C:10]=1[NH:11][C:12](=[O:33])[N:13]2[C:18]1[CH:19]=[C:20]([N:24]([CH3:32])[C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH:21]=[CH:22][CH:23]=1)C1C=CC=CC=1.Cl>CO.[OH-].[OH-].[Pd+2]>[NH2:8][C:9]1[N:17]=[CH:16][N:15]=[C:14]2[C:10]=1[NH:11][C:12](=[O:33])[N:13]2[C:18]1[CH:19]=[C:20]([N:24]([CH3:32])[C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:30])[CH3:28])[CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86691216tert-butyl 3-(6-(dibenzylamino)-8-oxo-7H-purin-9(8H)-yl)phenyl(methyl)carbamate

Product 1

HCID 86691218tert-butyl 3-(6-amino-8-oxo-7H-purin-9(8H)-yl)phenyl(methyl)carbamateYield 95.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of tert-butyl 3-(6-(dibenzylamino)-8-oxo-7H-purin-9(8H)-yl)phenyl(methyl)carbamate (23) (3 g, 5.6 mmol) in MeOH (120 mL) was added Pd(OH)2/C (3 g, 20 wt %) and 6 drops of con. HCl. The resulting mixture was purged with H2 (2×) before heated to 60° C. overnight under H2 atmosphere. The mixture was cooled to r.t., filtered through a Celite pad, and the solvent was removed in vacuo to give tert-butyl 3-(6-amino-8-oxo-7H-purin-9(8H)-yl)phenyl(methyl)carbamate (24) (1.9 g, 95%) as a light yellow solid. LC-MS (ESI): m/z (M+1) 357.

Workup

  1. customThe resulting mixture was purged with H2 (2×)
  2. temperatureThe mixture was cooled to r.t.
  3. filtrationfiltered through a Celite pad
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-263cab66ba58434d8e16089f4998398a
Source dataset
uspto-grants-2013_08
Patent number
US08501724B1

Reaction notes

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