Trifluoroacetic acid → 7-isobutyl-5-methyl-3-(phenylamino)-2-(4-(piperidin-2-yl)benzyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

HRID 81420Notes

Reaction equation

HRID 81420 reaction equation
[CH2:1]([N:5]1[C:10]2=[N:11][N:12]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([CH:28]4[CH2:33][CH2:32][CH2:31][CH2:30][N:29]4C(OC(C)(C)C)=O)=[CH:24][CH:23]=3)[C:13]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:9]2[C:8](=[O:41])[N:7]([CH3:42])[C:6]1=[O:43])[CH:2]([CH3:4])[CH3:3].C(O)(C(F)(F)F)=O>ClCCl>[CH2:1]([N:5]1[C:10]2=[N:11][N:12]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]([CH:28]4[CH2:33][CH2:32][CH2:31][CH2:30][NH:29]4)=[CH:26][CH:27]=3)[C:13]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:9]2[C:8](=[O:41])[N:7]([CH3:42])[C:6]1=[O:43])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67109191Tert-butyl 2-(4-((7-isobutyl-5-methyl-4,6-dioxo-3-(phenylamino)-4,5,6,7-tetrahydropyrazolo[3,4-d]pyrimidin-2-yl)methyl)phenyl)piperidine-1-carboxylate

Product 1

HCID 426411137-isobutyl-5-methyl-3-(phenylamino)-2-(4-(piperidin-2-yl)benzyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dioneYield 50.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-butyl 2-(4-((7-isobutyl-5-methyl-4,6-dioxo-3-(phenylamino)-4,5,6,7-tetrahydropyrazolo[3,4-d]pyrimidin-2-yl)methyl)phenyl)piperidine-1-carboxylate (76 mg) is dissolved in 2 mL of dichloromethane, and then TFA (2 mL) is added. The mixture is stirred at room temperature for an hour. After evaporation, the residue is purified by a semi-preparative HPLC to give 32 mg of pure product as white solids. MS (ESI) m/z 487.3 [M+H]+.

Workup

  1. customAfter evaporation
  2. customthe residue is purified by a semi-preparative HPLC

Sources & evidence

ORD record
ord-7ae0785fe5e440bbaedcf1d248ac9db5
Source dataset
uspto-grants-2014_09
Patent number
US08846693B2

Reaction notes

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