N,N-Dimethylaniline → {2-[2-(4-Chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-5-methanesulfonyl-phenoxy]-ethyl}-dimethyl-amine

HRID 1864138Notes

Reaction equation

HRID 1864138 reaction equation
[CH3:1][N:2]([CH3:26])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:9]=[CH:8][C:7]=1[N:16]1[C:20]2=[N:21][CH:22]=[N:23][C:24](O)=[C:19]2[CH:18]=[N:17]1.O=P(Cl)(Cl)[Cl:29].CN(C)C1C=CC=CC=1>>[Cl:29][C:24]1[N:23]=[CH:22][N:21]=[C:20]2[N:16]([C:7]3[CH:8]=[CH:9][C:10]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:11][C:6]=3[O:5][CH2:4][CH2:3][N:2]([CH3:26])[CH3:1])[N:17]=[CH:18][C:19]=12

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178483892HCID 178483892, compound

Product 1

HCID 21897434{2-[2-(4-Chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-5-methanesulfonyl-phenoxy]-ethyl}-dimethyl-amine

Conditions

Temperature
100 °C

Procedure

In a reaction vial was placed a stir bar, 1-[2-(2-dimethylamino-ethoxy)-4-methanesulfonyl-phenyl]-1H-pyrazolo[3,4-d]pyrimidin-4-ol (50 mg), POCl3 (0.5 mL) and N,N-dimethylaniline (15 μl). The reaction mixture was stirred at 100° C. for 1 hour. Upon cooling the reaction mixture to the room temperature, a white precipitate formed. The mixture was left sealed over the weekend at room temperature. After concentrated under the vacuum, the residue was washed with Et2O and filtered to give {2-[2-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-5-methanesulfonyl-phenoxy]-ethyl}-dimethyl-amine as a white solid. Exact mass calculated for C16H18ClN5O3S 395.08, found 396 (MH+).

Workup

  1. temperatureUpon cooling the reaction mixture to the room temperature
  2. customa white precipitate formed
  3. waitThe mixture was left
  4. customsealed over the weekend at room temperature
  5. concentrationAfter concentrated under the vacuum
  6. washthe residue was washed with Et2O
  7. filtrationfiltered

Sources & evidence

ORD record
ord-a9aec5f9b1e04d19a7803616c9f48cf8
Source dataset
uspto-grants-2009_12
Patent number
US07625906B2

Reaction notes

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