Cesium carbonate → 1-(2-Fluorobenzyl)-3-iodo-6-methyl-1H-pyrazolo[3,4-d]pyrimidine

HRID 570525Notes

Reaction equation

HRID 570525 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([CH3:11])=[N:8][CH:9]=2)[NH:4][N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21]Br>CN(C=O)C.O>[F:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21][N:4]1[C:5]2=[N:6][C:7]([CH3:11])=[N:8][CH:9]=[C:10]2[C:2]([I:1])=[N:3]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 67968alpha-Bromo-o-fluorotolueneHCID 178432607HCID 178432607, compound

Product 1

HCID 712854301-(2-Fluorobenzyl)-3-iodo-6-methyl-1H-pyrazolo[3,4-d]pyrimidineYield 20.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

7.950 g (13.76 mmol) of 3-iodo-6-methyl-1H-pyrazolo[3,4-d]pyrimidine and 4.930 g (15.13 mmol) of caesium carbonate were initially charged in 20 ml of DMF, and 2.860 g (15.13 mmol) of 2-fluorobenzyl bromide dissolved in 5 ml of DMF were added. The reaction mixture was stirred at RT overnight, diluted with 100 ml of water and extracted with ethyl acetate. The organic phase was dried over sodium sulphate and concentrated on a rotary evaporator. The residue was purified by means of preparative HPLC (eluent: acetonitrile/water, gradient 30:70→95:5). 1.030 g of the target compound were obtained (20% of theory).

Workup

  1. additionwere added
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. concentrationconcentrated on a rotary evaporator
  5. customThe residue was purified by means of preparative HPLC (eluent: acetonitrile/water, gradient 30:70→95:5)

Sources & evidence

ORD record
ord-e5c82e039aea41ff92bd6a43497a909d
Source dataset
uspto-grants-2015_05
Patent number
US09023849B2

Reaction notes

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