Cesium carbonate → HCID 22346783, compound

HRID 1910001Notes

Reaction equation

HRID 1910001 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[NH:4][N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:19][CH2:20][OH:21]>CN(C)C=O>[NH2:11][C:9]1[N:8]=[CH:7][N:6]=[C:5]2[N:4]([CH2:19][CH2:20][OH:21])[N:3]=[C:2]([I:1])[C:10]=12

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 108982-BromoethanolHCID 178508725HCID 178508725, compound

Product 1

HCID 22346783HCID 22346783, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (200 mg, 0.766 mmol) in N,N-Dimethylformamide (DMF) (5 mL) was added cesium carbonate (300 mg, 0.919 mmol) followed by 2-bromoethanol (0.057 mL, 0.805 mmol), and the reaction mixture was stirred over the weekend (3 days) at 80 C into a sealed vessel. The reaction was allowed to cool down to room temperature. The mixture was concentrated and treated with water (˜10 mL). The resulting aqueous mixture was sonicated, and then filtered. The solid in the filter was washed with water (2×10 mL) to afford 2-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethanol (128 mg) as a white solid after drying. LC/MS (ES) m/z=306.0 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated
  2. additiontreated with water (˜10 mL)
  3. customThe resulting aqueous mixture was sonicated
  4. filtrationfiltered
  5. washThe solid in the filter was washed with water (2×10 mL)

Sources & evidence

ORD record
ord-c2bb6e1b13124723ae4b46d9fe316a54
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

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