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

HRID 570531Notes

Reaction equation

HRID 570531 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[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21]Br>CN(C=O)C>[F:18][C:19]1[C:26]([F:27])=[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

5

Reactant 3

HCID 10796Cesium carbonateHCID 5179841-(Bromomethyl)-2,3-difluoro-benzeneHCID 178432607HCID 178432607, compound

Product 1

HCID 866920981-(2,3-Difluorobenzyl)-3-iodo-6-methyl-1H-pyrazolo[3,4-d]pyrimidineYield 32.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

7.100 g (approx. 10.92 mmol, purity 40%) of 3-iodo-6-methyl-1H-pyrazolo[3,4-d]pyrimidine and 4.626 g (14.20 mmol) of caesium carbonate were initially charged in 100 ml of DMF, and 2.939 g (14.20 mmol) of 2,3-difluorobenzyl bromide dissolved in 50 ml of DMF were added. The reaction mixture was stirred at RT for 3 h, added to 1.5 l of ice-water and extracted with diethyl ether. 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). 1.360 g of the target compound were obtained (31% of theory).

Workup

  1. additionwere added
  2. extractionextracted with diethyl ether
  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-3a907081e4c0412c88d307d7936cf419
Source dataset
uspto-grants-2015_05
Patent number
US09023849B2

Reaction notes

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