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

HRID 1887055Notes

Reaction equation

HRID 1887055 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]([C:27]1[CH:32]=[CH:31][C:30]([O:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[CH:29][CH:28]=1)[C:5](=[O:26])[N:6]2[C:11]1[CH:12]=[C:13]([N:17](C)[C:18](=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:27]1[CH:32]=[CH:31][C:30]([O:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)=[CH:29][CH:28]=1)[C:5](=[O:26])[N:6]2[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([NH:17][CH3:18])[CH:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86691219tert-butyl 3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)phenyl(methyl)carbamate

Product 1

HCID 866912206-amino-9-(3-(methylamino)phenyl)-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)phenyl(methyl)carbamate (31) (450 mg, 0.86 mmol) in DCM (8 mL) was added TFA (2 mL) dropwise. The reaction mixture was stirred at rt for 1 h and then concentrated. The residue was purified by column chromatography (silica gel, 0 to 10% methanol in methylene chloride (0.3% Et3N)) to give 6-amino-9-(3-(methylamino)phenyl)-7-(4-phenoxyphenyl)-7H-purin-8(9H)-one (32) (364 mg, 100%). LC-MS (ESI): m/z (M+1) 425.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by column chromatography (silica gel, 0 to 10% methanol in methylene chloride (0.3% Et3N))

Sources & evidence

ORD record
ord-f509a64986d042528b7adaba812e5bdd
Source dataset
uspto-grants-2013_08
Patent number
US08501724B1

Reaction notes

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