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

HRID 536498Notes

Reaction equation

HRID 536498 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 put in 20 ml DMF and 2.860 g (15.13 mmol) of 2-fluorobenzyl bromide dissolved in 5 ml DMF was added. The reaction mixture was stirred overnight at RT, diluted with 100 ml water and extracted with ethyl acetate. The organic phase was dried over sodium sulphate and concentrated in a rotary evaporator. The residue was purified by preparative HPLC (eluent: acetonitrile/water, gradient 30:70→95:5). 1.030 g of the target compound was obtained (20% of theor.).

Workup

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

Sources & evidence

ORD record
ord-20fb8cc509ef46789fc0a502cfe0c260
Source dataset
uspto-grants-2014_10
Patent number
US08859569B2

Reaction notes

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