Nitrogen → HCID 178483892, compound

HRID 719492

Reaction equation

HRID 719492 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH2:6][CH2:7][OH:8])[CH3:5].N#N.F[C:12]1[CH:17]=[C:16]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:15]=[CH:14][C:13]=1[N:22]1[C:26]2=[N:27][CH:28]=[N:29][C:30]([OH:31])=[C:25]2[CH:24]=[N:23]1>O1CCOCC1>[CH3:3][N:4]([CH3:5])[CH2:6][CH2:7][O:8][C:12]1[CH:17]=[C:16]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:15]=[CH:14][C:13]=1[N:22]1[C:26]2=[N:27][CH:28]=[N:29][C:30]([OH:31])=[C:25]2[CH:24]=[N:23]1

Participants

6

Reactant 4

HCID 947NitrogenHCID 79022-(Dimethylamino)ethanolHCID 24758Sodium hydrideHCID 178504786HCID 178504786, compound

Product 1

HCID 178483892HCID 178483892, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

In a reaction vial was placed a stir bar and NaH (60% in oil, 90 mg). Dimethylaminoethanol (200 mg) was dissolved in dioxane (1.5 mL) and added to the reaction vial under N2. The mixture was stirred at room temperature for 1 hour before 1-(2-fluoro-4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ol (50 mg) was added. The reaction mixture was heated at 70° C. for 60 hours. The resulting solution was concentrated under vacuum and 1-[2-(2-dimethylamino-ethoxy)-4-methanesulfonyl-phenyl]-1H-pyrazolo[3,4-d]pyrimidin-4-ol was purified by preparative HPLC. 1H NMR (DMSO-d6, 400 MHz) δ 2.68 (s, 6H), 3.36 (s, 3H), 3.40 (m, 2H), 4.54 (m, 2H), 7.74 (m, 1H), 7.78 (m, 1H), 7.85 (m, 1H), 8.10 (s, 1H), 8.37 (s, 1H), 9.75 (s, 1H), 12.5 (s, 1H). Exact mass calculated for C16H19N5O4S 377.12, found 377.9 (MH+).

Workup

  1. additionwas added
  2. concentrationThe resulting solution was concentrated under vacuum and 1-[2-(2-dimethylamino-ethoxy)-4-methanesulfonyl-phenyl]-1H-pyrazolo[3,4-d]pyrimidin-4-ol
  3. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-188c559e0fcc4c7bb4f266b0b6a57bca
Source dataset
uspto-grants-2006_11
Patent number
US07132426B2

Linked notes

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