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Cesium carbonate → 1-(2-Fluorobenzyl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidine

HRID 570538
Notes
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Reaction equation

HRID 570538 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][CH:9]=2)[NH:4][N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20]Br>CN(C=O)C.O>[F:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20][N:4]1[C:5]2=[N:6][CH:7]=[N:8][CH:9]=[C:10]2[C:2]([I:1])=[N:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 67968alpha-Bromo-o-fluorotolueneHCID 178506576HCID 178506576, compound

Product 1

HCID 866921041-(2-Fluorobenzyl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidineYield 89.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6228
Dimethylformamide
Solvent
2×

Procedure

569 mg (2.313 mmol) of 3-iodo-1H-pyrazolo[3,4-d]pyrimidine and 828 mg (2.544 mmol) of caesium carbonate were initially charged in 10 ml of DMF, and 481 mg (2.544 mmol) of 2-fluorobenzyl bromide dissolved in 2 ml of DMF were added. The reaction mixture was stirred at RT overnight, diluted with 50 ml of water and filtered with suction, and the residue was dried under high vacuum. 733 mg of the target compound were obtained (purity 83%; 74% of theory).

Workup

  1. additionwere added
  2. filtrationfiltered with suction
  3. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-64df922a521f4246bdf9bcf7c4a82a29
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09023849B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes