Aniline → 1-(but-3-enyl)-N3-(2,6-dimethylphenyl)-N6-phenyl-1H-pyrazolo[3,4-d]pyrimidine-3,6-diamine

HRID 2357981Notes

Reaction equation

HRID 2357981 reaction equation
[CH2:1]([N:5]1[C:9]2=[N:10][C:11](Cl)=[N:12][CH:13]=[C:8]2[C:7]([NH:15][C:16]2[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:23])=[N:6]1)[CH2:2][CH:3]=[CH2:4].[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(O)(C(F)(F)F)=O>O1CCOCC1>[CH2:1]([N:5]1[C:9]2=[N:10][C:11]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[N:12][CH:13]=[C:8]2[C:7]([NH:15][C:16]2[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:23])=[N:6]1)[CH2:2][CH:3]=[CH2:4]

Participants

5

Reactant 3

HCID 6115AnilineHCID 6422Trifluoroacetic acidHCID 588368811-(but-3-enyl)-6-chloro-N-(2,6-dimethylphenyl)-1H-pyrazolo[3,4-d]pyrimidin-3-amine

Product 1

HCID 160487521-(but-3-enyl)-N3-(2,6-dimethylphenyl)-N6-phenyl-1H-pyrazolo[3,4-d]pyrimidine-3,6-diamine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 815 mg (2.5 mmol) of 1-(but-3-enyl)-6-chloro-N-(2,6-dimethylphenyl)-1H-pyrazolo[3,4-d]pyrimidin-3-amine 32 (Example 1, Step D) in 17 mL of 1,4-dioxane was treated sequentially with 280 μl (3.1 mmol) of aniline and 415 μl (5.6 mmol) of TFA. The resulting orange solution was heated at reflux for 6 h, and then was concentrated. The residue was purified by chromatography on silica gel (hexanes:EtOAc, 3:1) to give the title compound 33. 1H-NMR (DMSO-d6) δ 2.24 (s, 6H), 2.45-2.52 (m, 2H), 4.08 (t, J=6.8 Hz, 2H), 4.94 (d, J=10.2 Hz, 1.1 Hz, 1H), 5.02 (dd, J=17.2 Hz, 1.6 Hz, 1H), 5.78-5.88 (m, 1H), 6.95 (t, J=7.3 Hz, 1H), 7.06-7.14 (m, 3H), 7.28 (t, J=8.0 Hz, 2H), 7.84 (d, J=8.0 Hz, 2H), 8.10 (s, 1H), 8.39 (s, 1H), 9.66 (s, 1H). Mass Spectrum (ESI) m/e=385.2 (M+1).

Workup

  1. temperatureThe resulting orange solution was heated
  2. temperatureat reflux for 6 h
  3. concentrationwas concentrated
  4. customThe residue was purified by chromatography on silica gel (hexanes:EtOAc, 3:1)

Sources & evidence

ORD record
ord-0b5c42c2741b41999a33c748b81bf55c
Source dataset
uspto-grants-2010_07
Patent number
US07763624B2

Reaction notes

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