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

HRID 1887041Notes

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:32])[N:13]2[C:18]1[CH:19]=[C:20]([NH:24][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:32])[N:13]2[C:18]1[CH:19]=[C:20]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:28])([CH3:30])[CH3:29])[CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of tert-butyl 3-(6-(dibenzylamino)-8-oxo-7H-purin-9(8H)-yl)phenylcarbamate (4) (3.0 g, 5.7 mmol) in 120 mL MeOH was added 3.0 g Pd(OH)2/C (20 wt %) and 6 drops of con. HCl. After two vacuum/H2 cycles to remove air from the reaction flask, the stirred mixture was heated at 60° C. under hydrogen atmosphere overnight. The reaction mixture was filtered through a Celite pad and the filtrate was concentrated to dryness in vacuo. The residue was purified by column chromatography (silica gel, 0 to 5% methanol in DCM) to give tert-butyl 3-(6-amino-8-oxo-7H-purin-9(8H)-yl)phenylcarbamate (5) (1.5 g, 76%) as a white solid. LC-MS (ESI): m/z (M+1) 343.

Workup

customAfter two vacuum/H2 cycles to remove air from the reaction flask
filtrationThe reaction mixture was filtered through a Celite pad
concentrationthe filtrate was concentrated to dryness in vacuo
customThe residue was purified by column chromatography (silica gel, 0 to 5% methanol in DCM)

Sources & evidence

ORD record: ord-b97a36d0c15943a6aac5d6f0855c700c
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501724B1

Reaction notes

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