Trifluoroacetic acid → 6-amino-9-(3-aminophenyl)-7-(4-phenoxyphenyl)-7H-purin-8(9H)-one

HRID 1887043Notes

Reaction equation

HRID 1887043 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]([C:26]1[CH:31]=[CH:30][C:29]([O:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:28][CH:27]=1)[C:5](=[O:25])[N:6]2[C:11]1[CH:12]=[C:13]([NH:17]C(=O)OC(C)(C)C)[CH:14]=[CH:15][CH:16]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]([C:26]1[CH:31]=[CH:30][C:29]([O:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[CH:28][CH:27]=1)[C:5](=[O:25])[N:6]2[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([NH2:17])[CH:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86761988tert-butyl 3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)phenylcarbamate

Product 1

HCID 866912136-amino-9-(3-aminophenyl)-7-(4-phenoxyphenyl)-7H-purin-8(9H)-oneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)phenylcarbamate (6) (404 mg, 0.8 mmol) in 8 mL DCM was added 2 mL TFA dropwise. The reaction mixture was stirred at rt for 1 hr, then concentrated to dryness. The residue was purified by column chromatography (silica gel, 0 to 5% methanol in DCM (0.3% Et3N)) to give 6-amino-9-(3-aminophenyl)-7-(4-phenoxyphenyl)-7H-purin-8(9H)-one (7) (325 mg, 100%) as a yellow solid. LC-MS (ESI): m/z (M+1) 411.

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue was purified by column chromatography (silica gel, 0 to 5% methanol in DCM (0.3% Et3N))

Sources & evidence

ORD record
ord-a6d7668db5b04c7a823b71691193be7f
Source dataset
uspto-grants-2013_08
Patent number
US08501724B1

Reaction notes

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