Trifluoroacetic acid → Trifluoroacetic acid

HRID 928231Notes

Reaction equation

HRID 928231 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]2[N:9]([CH2:19][CH:20]3[CH2:25][CH2:24][CH:23]([NH:26]C(=O)OC(C)(C)C)[CH2:22][CH2:21]3)[N:10]=[C:11]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)[C:6]2=[CH:5][N:4]=1.[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37]>C(Cl)Cl>[NH2:26][CH:23]1[CH2:22][CH2:21][CH:20]([CH2:19][N:9]2[C:7]3=[N:8][C:3]([NH:2][CH3:1])=[N:4][CH:5]=[C:6]3[C:11]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)=[N:10]2)[CH2:25][CH2:24]1.[C:36]([OH:38])([C:35]([F:40])([F:39])[F:34])=[O:37]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68212721tert-butyl 4-((6-(methylamino)-3-p-tolyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)cyclohexylcarbamate

Product 2

HCID 6422Trifluoroacetic acidHCID 674709741-((4-aminocyclohexyl)methyl)-N-methyl-3-p-tolyl-1H-pyrazolo[3,4-d]pyrimidin-6-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-((6-(methylamino)-3-p-tolyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)cyclohexylcarbamate (0.064 g, 0.14 mmol) in CH2Cl2 (2 mL) was added trifluoroacetic acid (0.6 mL) at ambient temperature. After stirring for 2 h, the solvent was evaporated. The residue was purified by preparative HPLC to provide 1-((4-aminocyclohexyl)methyl)-N-methyl-3-p-tolyl-1H-pyrazolo[3,4-d]pyrimidin-6-amine (UNC00000478A) as a yellow solid (TFA salt) (0.063 g, 95%). MS m/z 351.3 [M+H]+.

Workup

  1. customthe solvent was evaporated
  2. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-e1f8dd7f78b5471f95486e2fef78b7f3
Source dataset
uspto-grants-2016_03
Patent number
US09290499B2

Reaction notes

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